diff --git a/src/Umbraco.Configuration/Legacy/HostingSettings.cs b/src/Umbraco.Configuration/Legacy/HostingSettings.cs
index d0d09ea86f..1858e8a4a4 100644
--- a/src/Umbraco.Configuration/Legacy/HostingSettings.cs
+++ b/src/Umbraco.Configuration/Legacy/HostingSettings.cs
@@ -19,6 +19,8 @@ namespace Umbraco.Core.Configuration.Legacy
             }
         }
 
+        public string ApplicationVirtualPath => null;
+
         /// <summary>
         /// Gets a value indicating whether umbraco is running in [debug mode].
         /// </summary>
diff --git a/src/Umbraco.Configuration/Models/HostingSettings.cs b/src/Umbraco.Configuration/Models/HostingSettings.cs
index 7cfc08d2d4..f0fbcf4cab 100644
--- a/src/Umbraco.Configuration/Models/HostingSettings.cs
+++ b/src/Umbraco.Configuration/Models/HostingSettings.cs
@@ -18,6 +18,8 @@ namespace Umbraco.Configuration.Models
         public LocalTempStorage LocalTempStorageLocation =>
             _configuration.GetValue(Prefix+"LocalTempStorage", LocalTempStorage.Default);
 
+        public string ApplicationVirtualPath => null;
+
         /// <summary>
         ///     Gets a value indicating whether umbraco is running in [debug mode].
         /// </summary>
diff --git a/src/Umbraco.Core/Configuration/GlobalSettingsExtensions.cs b/src/Umbraco.Core/Configuration/GlobalSettingsExtensions.cs
new file mode 100644
index 0000000000..a9a7f578d0
--- /dev/null
+++ b/src/Umbraco.Core/Configuration/GlobalSettingsExtensions.cs
@@ -0,0 +1,58 @@
+using System;
+using Umbraco.Core.Hosting;
+
+namespace Umbraco.Core.Configuration
+{
+    public static class GlobalSettingsExtensions
+    {
+        private static string _mvcArea;
+        private static string _backOfficePath;
+
+        /// <summary>
+        /// Returns the absolute path for the Umbraco back office
+        /// </summary>
+        /// <param name="globalSettings"></param>
+        /// <param name="hostingEnvironment"></param>
+        /// <returns></returns>
+        public static string GetBackOfficePath(this IGlobalSettings globalSettings, IHostingEnvironment hostingEnvironment)
+        {
+            if (_backOfficePath != null) return _backOfficePath;
+            _backOfficePath = hostingEnvironment.ToAbsolute(globalSettings.UmbracoPath);
+            return _backOfficePath;
+        }
+
+        /// <summary>
+        /// This returns the string of the MVC Area route.
+        /// </summary>
+        /// <remarks>
+        /// This will return the MVC area that we will route all custom routes through like surface controllers, etc...
+        /// We will use the 'Path' (default ~/umbraco) to create it but since it cannot contain '/' and people may specify a path of ~/asdf/asdf/admin
+        /// we will convert the '/' to '-' and use that as the path. its a bit lame but will work.
+        ///
+        /// We also make sure that the virtual directory (SystemDirectories.Root) is stripped off first, otherwise we'd end up with something
+        /// like "MyVirtualDirectory-Umbraco" instead of just "Umbraco".
+        /// </remarks>
+        public static string GetUmbracoMvcArea(this IGlobalSettings globalSettings, IHostingEnvironment hostingEnvironment)
+        {
+            if (_mvcArea != null) return _mvcArea;
+
+            _mvcArea = globalSettings.GetUmbracoMvcAreaNoCache(hostingEnvironment);
+
+            return _mvcArea;
+        }
+
+        internal static string GetUmbracoMvcAreaNoCache(this IGlobalSettings globalSettings, IHostingEnvironment hostingEnvironment)
+        {
+            var path = string.IsNullOrEmpty(globalSettings.UmbracoPath)
+                ? string.Empty
+                : hostingEnvironment.ToAbsolute(globalSettings.UmbracoPath);
+
+            if (path.IsNullOrWhiteSpace())
+                throw new InvalidOperationException("Cannot create an MVC Area path without the umbracoPath specified");
+
+            if (path.StartsWith(hostingEnvironment.ApplicationVirtualPath)) // beware of TrimStart, see U4-2518
+                path = path.Substring(hostingEnvironment.ApplicationVirtualPath.Length);
+            return path.TrimStart('~').TrimStart('/').Replace('/', '-').Trim().ToLower();
+        }
+    }
+}
diff --git a/src/Umbraco.Core/Configuration/IHostingSettings.cs b/src/Umbraco.Core/Configuration/IHostingSettings.cs
index ef399177a4..48ff4f216e 100644
--- a/src/Umbraco.Core/Configuration/IHostingSettings.cs
+++ b/src/Umbraco.Core/Configuration/IHostingSettings.cs
@@ -1,11 +1,24 @@
+using Umbraco.Core.Hosting;
+
 namespace Umbraco.Core.Configuration
 {
     public interface IHostingSettings
     {
         bool DebugMode { get; }
+
         /// <summary>
         /// Gets the configuration for the location of temporary files.
         /// </summary>
         LocalTempStorage LocalTempStorageLocation { get; }
+
+        /// <summary>
+        /// Optional property to explicitly configure the application's virtual path
+        /// </summary>
+        /// <remarks>
+        /// By default this is null which will mean that the <see cref="IHostingEnvironment.ApplicationVirtualPath"/> is automatically configured,
+        /// otherwise this explicitly sets it. 
+        /// If set, this value must begin with a "/" and cannot end with "/".
+        /// </remarks>
+        string ApplicationVirtualPath { get; }
     }
 }
diff --git a/src/Umbraco.Core/Hosting/IHostingEnvironment.cs b/src/Umbraco.Core/Hosting/IHostingEnvironment.cs
index 1ef66c66bb..0bdfe5c425 100644
--- a/src/Umbraco.Core/Hosting/IHostingEnvironment.cs
+++ b/src/Umbraco.Core/Hosting/IHostingEnvironment.cs
@@ -9,13 +9,23 @@ namespace Umbraco.Core.Hosting
         string ApplicationPhysicalPath { get; }
 
         string LocalTempPath { get; }
+
+        /// <summary>
+        /// The web application's hosted path
+        /// </summary>
+        /// <remarks>
+        /// In most cases this will return "/" but if the site is hosted in a virtual directory then this will return the virtual directory's path such as "/mysite".
+        /// This value must begin with a "/" and cannot end with "/".
+        /// </remarks>
         string ApplicationVirtualPath { get; }
 
         bool IsDebugMode { get; }
+
         /// <summary>
         /// Gets a value indicating whether Umbraco is hosted.
         /// </summary>
         bool IsHosted { get; }
+
         Version IISVersion { get; }
         string MapPath(string path);
 
diff --git a/src/Umbraco.Core/IO/IIOHelper.cs b/src/Umbraco.Core/IO/IIOHelper.cs
index dccd394817..ee36b2a96b 100644
--- a/src/Umbraco.Core/IO/IIOHelper.cs
+++ b/src/Umbraco.Core/IO/IIOHelper.cs
@@ -4,10 +4,9 @@ namespace Umbraco.Core.IO
 {
     public interface IIOHelper
     {
-
-        string BackOfficePath { get; }
-
+        // TODO: There is no need for this, we should just use Path.DirectorySeparatorChar which is cross platform, no need for an abstraction?
         char DirSepChar { get; }
+
         string FindFile(string virtualPath);
         
         // TODO: This is the same as IHostingEnvironment.ToAbsolute
@@ -57,12 +56,5 @@ namespace Umbraco.Core.IO
         /// <returns></returns>
         string GetRelativePath(string path);
 
-        // TODO: This is the same as IHostingEnvironment.ApplicationVirtualPath i don't think we want this
-        string Root
-        {
-            get;
-            set; //Only required for unit tests
-        }
-
     }
 }
diff --git a/src/Umbraco.Core/IO/IOHelper.cs b/src/Umbraco.Core/IO/IOHelper.cs
index 10ef478d26..91b1d70a11 100644
--- a/src/Umbraco.Core/IO/IOHelper.cs
+++ b/src/Umbraco.Core/IO/IOHelper.cs
@@ -13,29 +13,15 @@ namespace Umbraco.Core.IO
     public class IOHelper : IIOHelper
     {
         private readonly IHostingEnvironment _hostingEnvironment;
-        private readonly IGlobalSettings _globalSettings;
 
         public IOHelper(IHostingEnvironment hostingEnvironment, IGlobalSettings globalSettings)
         {
             _hostingEnvironment = hostingEnvironment ?? throw new ArgumentNullException(nameof(hostingEnvironment));
-            _globalSettings = globalSettings;
         }
 
-        public string BackOfficePath
-        {
-            get
-            {
-                var path = _globalSettings.UmbracoPath;
-
-                return string.IsNullOrEmpty(path) ? string.Empty : ResolveUrl(path);
-            }
-        }
-
-
         // static compiled regex for faster performance
         //private static readonly Regex ResolveUrlPattern = new Regex("(=[\"\']?)(\\W?\\~(?:.(?![\"\']?\\s+(?:\\S+)=|[>\"\']))+.)[\"\']?", RegexOptions.Compiled | RegexOptions.IgnoreCase | RegexOptions.IgnorePatternWhitespace);
 
-
         public char DirSepChar => Path.DirectorySeparatorChar;
 
         //helper to try and match the old path to a new virtual one
@@ -44,10 +30,10 @@ namespace Umbraco.Core.IO
             string retval = virtualPath;
 
             if (virtualPath.StartsWith("~"))
-                retval = virtualPath.Replace("~", Root);
+                retval = virtualPath.Replace("~", _hostingEnvironment.ApplicationVirtualPath);
 
-            if (virtualPath.StartsWith("/") && virtualPath.StartsWith(Root) == false)
-                retval = Root + "/" + virtualPath.TrimStart('/');
+            if (virtualPath.StartsWith("/") && virtualPath.StartsWith(_hostingEnvironment.ApplicationVirtualPath) == false)
+                retval = _hostingEnvironment.ApplicationVirtualPath + "/" + virtualPath.TrimStart('/');
 
             return retval;
         }
@@ -65,7 +51,7 @@ namespace Umbraco.Core.IO
             try
             {
                 if (virtualPath.StartsWith("~"))
-                    return Attempt.Succeed(virtualPath.Replace("~", Root).Replace("//", "/"));
+                    return Attempt.Succeed(virtualPath.Replace("~", _hostingEnvironment.ApplicationVirtualPath).Replace("//", "/"));
                 if (Uri.IsWellFormedUriString(virtualPath, UriKind.Absolute))
                     return Attempt.Succeed(virtualPath);
 
@@ -93,8 +79,8 @@ namespace Umbraco.Core.IO
 
             if (_hostingEnvironment.IsHosted)
             {
-                var result = (String.IsNullOrEmpty(path) == false && (path.StartsWith("~") || path.StartsWith(Root)))
-                        ?  _hostingEnvironment.MapPath(path)
+                var result = (!string.IsNullOrEmpty(path) && (path.StartsWith("~") || path.StartsWith(_hostingEnvironment.ApplicationVirtualPath)))
+                    ? _hostingEnvironment.MapPath(path)
                     : _hostingEnvironment.MapPath("~/" + path.TrimStart('/'));
 
                 if (result != null) return result;
@@ -136,7 +122,7 @@ namespace Umbraco.Core.IO
             // TODO: what's below is dirty, there are too many ways to get the root dir, etc.
             // not going to fix everything today
 
-            var mappedRoot = MapPath(Root);
+            var mappedRoot = MapPath(_hostingEnvironment.ApplicationVirtualPath);
             if (filePath.StartsWith(mappedRoot) == false)
                 filePath = MapPath(filePath);
 
@@ -204,32 +190,5 @@ namespace Umbraco.Core.IO
             return PathUtility.EnsurePathIsApplicationRootPrefixed(path);
         }
 
-        private string _root;
-
-        /// <summary>
-        /// Gets the root path of the application
-        /// </summary>
-        /// <remarks>
-        /// In most cases this will be an empty string which indicates the app is not running in a virtual directory.
-        /// This is NOT a physical path.
-        /// </remarks>
-        public string Root
-        {
-            get
-            {
-                if (_root != null) return _root;
-
-                var appPath = _hostingEnvironment.ApplicationVirtualPath;
-                // ReSharper disable once ConditionIsAlwaysTrueOrFalse
-                if (appPath == null || appPath == "/")
-                    appPath = string.Empty;
-
-                _root = appPath;
-
-                return _root;
-            }
-            //Only required for unit tests
-            set => _root = value;
-        }
     }
 }
diff --git a/src/Umbraco.Core/IO/IOHelperExtensions.cs b/src/Umbraco.Core/IO/IOHelperExtensions.cs
index 39bd5e6cc9..0e35f3b87b 100644
--- a/src/Umbraco.Core/IO/IOHelperExtensions.cs
+++ b/src/Umbraco.Core/IO/IOHelperExtensions.cs
@@ -5,8 +5,6 @@ namespace Umbraco.Core.IO
 {
     public static class IOHelperExtensions
     {
-        private static string _mvcArea;
-
         /// <summary>
         /// Tries to create a directory.
         /// </summary>
@@ -38,37 +36,6 @@ namespace Umbraco.Core.IO
             return "umbraco-test." + Guid.NewGuid().ToString("N").Substring(0, 8);
         }
 
-        /// <summary>
-        /// This returns the string of the MVC Area route.
-        /// </summary>
-        /// <remarks>
-        /// This will return the MVC area that we will route all custom routes through like surface controllers, etc...
-        /// We will use the 'Path' (default ~/umbraco) to create it but since it cannot contain '/' and people may specify a path of ~/asdf/asdf/admin
-        /// we will convert the '/' to '-' and use that as the path. its a bit lame but will work.
-        ///
-        /// We also make sure that the virtual directory (SystemDirectories.Root) is stripped off first, otherwise we'd end up with something
-        /// like "MyVirtualDirectory-Umbraco" instead of just "Umbraco".
-        /// </remarks>
-        public static string GetUmbracoMvcArea(this IIOHelper ioHelper)
-        {
-            if (_mvcArea != null) return _mvcArea;
-
-            _mvcArea = GetUmbracoMvcAreaNoCache(ioHelper);
-
-            return _mvcArea;
-        }
-
-        internal static string GetUmbracoMvcAreaNoCache(this IIOHelper ioHelper)
-        {
-            if (ioHelper.BackOfficePath.IsNullOrWhiteSpace())
-            {
-                throw new InvalidOperationException("Cannot create an MVC Area path without the umbracoPath specified");
-            }
-
-            var path = ioHelper.BackOfficePath;
-            if (path.StartsWith(ioHelper.Root)) // beware of TrimStart, see U4-2518
-                path = path.Substring(ioHelper.Root.Length);
-            return path.TrimStart('~').TrimStart('/').Replace('/', '-').Trim().ToLower();
-        }
+       
     }
 }
diff --git a/src/Umbraco.Core/UriExtensions.cs b/src/Umbraco.Core/UriExtensions.cs
index e7be0b6500..a8aa6f8c91 100644
--- a/src/Umbraco.Core/UriExtensions.cs
+++ b/src/Umbraco.Core/UriExtensions.cs
@@ -3,6 +3,7 @@ using System.IO;
 using System.Linq;
 using Umbraco.Composing;
 using Umbraco.Core.Configuration;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.IO;
 
 namespace Umbraco.Core
@@ -16,44 +17,42 @@ namespace Umbraco.Core
         ///  Checks if the current uri is a back office request
         ///  </summary>
         ///  <param name="url"></param>
-        ///  <param name="applicationPath">
-        ///  The current application path or VirtualPath
-        ///  </param>
-        /// <param name="globalSettings"></param>
-        ///  <param name="ioHelper"></param>
+        ///  <param name="globalSettings"></param>
+        ///  <param name="hostingEnvironment"></param>
         ///  <returns></returns>
         ///  <remarks>
         ///  There are some special routes we need to check to properly determine this:
-        ///
+        /// 
         ///      If any route has an extension in the path like .aspx = back office
-        ///
+        /// 
         ///      These are def back office:
         ///          /Umbraco/BackOffice     = back office
         ///          /Umbraco/Preview        = back office
         ///      If it's not any of the above, and there's no extension then we cannot determine if it's back office or front-end
         ///      so we can only assume that it is not back office. This will occur if people use an UmbracoApiController for the backoffice
         ///      but do not inherit from UmbracoAuthorizedApiController and do not use [IsBackOffice] attribute.
-        ///
+        /// 
         ///      These are def front-end:
         ///          /Umbraco/Surface        = front-end
         ///          /Umbraco/Api            = front-end
         ///      But if we've got this far we'll just have to assume it's front-end anyways.
-        ///
+        /// 
         ///  </remarks>
-        internal static bool IsBackOfficeRequest(this Uri url, string applicationPath, IIOHelper ioHelper)
+        internal static bool IsBackOfficeRequest(this Uri url, IGlobalSettings globalSettings, IHostingEnvironment hostingEnvironment)
         {
-            applicationPath = applicationPath ?? string.Empty;
-
+            var applicationPath = hostingEnvironment.ApplicationVirtualPath;
+            
             var fullUrlPath = url.AbsolutePath.TrimStart(new[] {'/'});
             var appPath = applicationPath.TrimStart(new[] {'/'});
             var urlPath = fullUrlPath.TrimStart(appPath).EnsureStartsWith('/');
 
             //check if this is in the umbraco back office
-            var isUmbracoPath = urlPath.InvariantStartsWith(ioHelper.BackOfficePath.EnsureStartsWith('/').TrimStart(appPath.EnsureStartsWith('/')).EnsureStartsWith('/'));
+            var backOfficePath = globalSettings.GetBackOfficePath(hostingEnvironment);
+            var isUmbracoPath = urlPath.InvariantStartsWith(backOfficePath.EnsureStartsWith('/').TrimStart(appPath.EnsureStartsWith('/')).EnsureStartsWith('/'));
             //if not, then def not back office
             if (isUmbracoPath == false) return false;
 
-            var mvcArea = ioHelper.GetUmbracoMvcArea();
+            var mvcArea = globalSettings.GetUmbracoMvcArea(hostingEnvironment);
             //if its the normal /umbraco path
             if (urlPath.InvariantEquals("/" + mvcArea)
                 || urlPath.InvariantEquals("/" + mvcArea + "/"))
@@ -108,9 +107,9 @@ namespace Umbraco.Core
         /// Checks if the current uri is an install request
         /// </summary>
         /// <param name="url"></param>
-        /// <param name="ioHelper"></param>
+        /// <param name="hostingEnvironment"></param>
         /// <returns></returns>
-        internal static bool IsInstallerRequest(this Uri url, IIOHelper ioHelper)
+        internal static bool IsInstallerRequest(this Uri url, IHostingEnvironment hostingEnvironment)
         {
             var authority = url.GetLeftPart(UriPartial.Authority);
             var afterAuthority = url.GetLeftPart(UriPartial.Query)
@@ -118,7 +117,7 @@ namespace Umbraco.Core
                                     .TrimStart("/");
 
             //check if this is in the umbraco back office
-            return afterAuthority.InvariantStartsWith(ioHelper.ResolveUrl("~/install").TrimStart("/"));
+            return afterAuthority.InvariantStartsWith(hostingEnvironment.ToAbsolute("~/install").TrimStart("/"));
         }
 
         /// <summary>
@@ -126,13 +125,15 @@ namespace Umbraco.Core
         /// </summary>
         /// <param name="url"></param>
         /// <param name="globalSettings"></param>
+        /// <param name="hostingEnvironment"></param>
         /// <returns></returns>
-        internal static bool IsDefaultBackOfficeRequest(this Uri url, IIOHelper ioHelper)
+        internal static bool IsDefaultBackOfficeRequest(this Uri url, IGlobalSettings globalSettings, IHostingEnvironment hostingEnvironment)
         {
-            if (url.AbsolutePath.InvariantEquals(ioHelper.BackOfficePath.TrimEnd("/"))
-                || url.AbsolutePath.InvariantEquals(ioHelper.BackOfficePath.EnsureEndsWith('/'))
-                || url.AbsolutePath.InvariantEquals(ioHelper.BackOfficePath.EnsureEndsWith('/') + "Default")
-                || url.AbsolutePath.InvariantEquals(ioHelper.BackOfficePath.EnsureEndsWith('/') + "Default/"))
+            var backOfficePath = globalSettings.GetBackOfficePath(hostingEnvironment);
+            if (url.AbsolutePath.InvariantEquals(backOfficePath.TrimEnd("/"))
+                || url.AbsolutePath.InvariantEquals(backOfficePath.EnsureEndsWith('/'))
+                || url.AbsolutePath.InvariantEquals(backOfficePath.EnsureEndsWith('/') + "Default")
+                || url.AbsolutePath.InvariantEquals(backOfficePath.EnsureEndsWith('/') + "Default/"))
             {
                 return true;
             }
diff --git a/src/Umbraco.Infrastructure/Models/Mapping/ContentTypeMapDefinition.cs b/src/Umbraco.Infrastructure/Models/Mapping/ContentTypeMapDefinition.cs
index 59f63f4f15..2e985bef07 100644
--- a/src/Umbraco.Infrastructure/Models/Mapping/ContentTypeMapDefinition.cs
+++ b/src/Umbraco.Infrastructure/Models/Mapping/ContentTypeMapDefinition.cs
@@ -10,6 +10,7 @@ using Umbraco.Core.PropertyEditors;
 using Umbraco.Web.Models.ContentEditing;
 using Umbraco.Core.Services;
 using Umbraco.Core.Exceptions;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.IO;
 using Umbraco.Core.Strings;
 
@@ -28,13 +29,13 @@ namespace Umbraco.Web.Models.Mapping
         private readonly IMemberTypeService _memberTypeService;
         private readonly ILogger _logger;
         private readonly IShortStringHelper _shortStringHelper;
-        private readonly IIOHelper _ioHelper;
         private readonly IGlobalSettings _globalSettings;
+        private readonly IHostingEnvironment _hostingEnvironment;
 
 
         public ContentTypeMapDefinition(PropertyEditorCollection propertyEditors, IDataTypeService dataTypeService, IFileService fileService,
             IContentTypeService contentTypeService, IMediaTypeService mediaTypeService, IMemberTypeService memberTypeService,
-            ILogger logger, IShortStringHelper shortStringHelper, IIOHelper ioHelper, IGlobalSettings globalSettings)
+            ILogger logger, IShortStringHelper shortStringHelper, IGlobalSettings globalSettings, IHostingEnvironment hostingEnvironment)
         {
             _propertyEditors = propertyEditors;
             _dataTypeService = dataTypeService;
@@ -44,8 +45,8 @@ namespace Umbraco.Web.Models.Mapping
             _memberTypeService = memberTypeService;
             _logger = logger;
             _shortStringHelper = shortStringHelper;
-            _ioHelper = ioHelper;
             _globalSettings = globalSettings;
+            _hostingEnvironment = hostingEnvironment;
         }
 
         public void DefineMaps(UmbracoMapper mapper)
@@ -191,7 +192,7 @@ namespace Umbraco.Web.Models.Mapping
             target.Icon = source.Icon;
             target.IconFilePath = target.IconIsClass
                 ? string.Empty
-                : $"{_ioHelper.BackOfficePath.EnsureEndsWith("/")}images/umbraco/{source.Icon}";
+                : $"{_globalSettings.GetBackOfficePath(_hostingEnvironment).EnsureEndsWith("/")}images/umbraco/{source.Icon}";
 
             target.Trashed = source.Trashed;
             target.Id = source.Id;
@@ -204,7 +205,7 @@ namespace Umbraco.Web.Models.Mapping
             target.Thumbnail = source.Thumbnail;
             target.ThumbnailFilePath = target.ThumbnailIsClass
                 ? string.Empty
-                : _ioHelper.ResolveUrl("~/umbraco/images/thumbnails/" + source.Thumbnail);
+                : _hostingEnvironment.ToAbsolute("~/umbraco/images/thumbnails/" + source.Thumbnail);
             target.UpdateDate = source.UpdateDate;
         }
 
@@ -497,7 +498,7 @@ namespace Umbraco.Web.Models.Mapping
             target.Icon = source.Icon;
             target.IconFilePath = target.IconIsClass
                 ? string.Empty
-                : $"{_ioHelper.BackOfficePath.EnsureEndsWith("/")}images/umbraco/{source.Icon}";
+                : $"{_globalSettings.GetBackOfficePath(_hostingEnvironment).EnsureEndsWith("/")}images/umbraco/{source.Icon}";
             target.Id = source.Id;
             target.IsContainer = source.IsContainer;
             target.IsElement = source.IsElement;
@@ -508,7 +509,7 @@ namespace Umbraco.Web.Models.Mapping
             target.Thumbnail = source.Thumbnail;
             target.ThumbnailFilePath = target.ThumbnailIsClass
                 ? string.Empty
-                : _ioHelper.ResolveUrl("~/umbraco/images/thumbnails/" + source.Thumbnail);
+                : _hostingEnvironment.ToAbsolute("~/umbraco/images/thumbnails/" + source.Thumbnail);
             target.Udi = MapContentTypeUdi(source);
             target.UpdateDate = source.UpdateDate;
 
@@ -540,7 +541,7 @@ namespace Umbraco.Web.Models.Mapping
             target.Icon = source.Icon;
             target.IconFilePath = target.IconIsClass
                 ? string.Empty
-                : $"{_ioHelper.BackOfficePath.EnsureEndsWith("/")}images/umbraco/{source.Icon}";
+                : $"{_globalSettings.GetBackOfficePath(_hostingEnvironment).EnsureEndsWith("/")}images/umbraco/{source.Icon}";
             target.Id = source.Id;
             target.IsContainer = source.IsContainer;
             target.IsElement = source.IsElement;
@@ -551,7 +552,7 @@ namespace Umbraco.Web.Models.Mapping
             target.Thumbnail = source.Thumbnail;
             target.ThumbnailFilePath = target.ThumbnailIsClass
                 ? string.Empty
-                : _ioHelper.ResolveUrl("~/umbraco/images/thumbnails/" + source.Thumbnail);
+                : _hostingEnvironment.ToAbsolute("~/umbraco/images/thumbnails/" + source.Thumbnail);
             target.Trashed = source.Trashed;
             target.Udi = source.Udi;
         }
diff --git a/src/Umbraco.Infrastructure/Runtime/CoreRuntime.cs b/src/Umbraco.Infrastructure/Runtime/CoreRuntime.cs
index 1cedca96dc..92e47771a6 100644
--- a/src/Umbraco.Infrastructure/Runtime/CoreRuntime.cs
+++ b/src/Umbraco.Infrastructure/Runtime/CoreRuntime.cs
@@ -231,8 +231,6 @@ namespace Umbraco.Core.Runtime
             // throws if not full-trust
             _umbracoBootPermissionChecker.ThrowIfNotPermissions();
 
-            ConfigureApplicationRootPath();
-
             // run handlers
             RuntimeOptions.DoRuntimeEssentials(_factory);
 
@@ -265,13 +263,6 @@ namespace Umbraco.Core.Runtime
             };
         }
 
-        protected virtual void ConfigureApplicationRootPath()
-        {
-            var path = GetApplicationRootPath();
-            if (string.IsNullOrWhiteSpace(path) == false)
-                IOHelper.Root = path;
-        }
-
         private bool AcquireMainDom(IMainDom mainDom, IApplicationShutdownRegistry applicationShutdownRegistry)
         {
             using (var timer = ProfilingLogger.DebugDuration<CoreRuntime>("Acquiring MainDom.", "Acquired."))
diff --git a/src/Umbraco.Infrastructure/Trees/TreeNode.cs b/src/Umbraco.Infrastructure/Trees/TreeNode.cs
index 7d3c657207..1b6945bcdd 100644
--- a/src/Umbraco.Infrastructure/Trees/TreeNode.cs
+++ b/src/Umbraco.Infrastructure/Trees/TreeNode.cs
@@ -3,6 +3,7 @@ using System.Collections.Generic;
 using System.Runtime.Serialization;
 using Umbraco.Composing;
 using Umbraco.Core;
+using Umbraco.Core.Configuration;
 using Umbraco.Web.Models.ContentEditing;
 
 namespace Umbraco.Web.Models.Trees
@@ -112,7 +113,8 @@ namespace Umbraco.Web.Models.Trees
                     return Current.IOHelper.ResolveUrl("~" + Icon.TrimStart('~'));
 
                 //legacy icon path
-                return string.Format("{0}images/umbraco/{1}", Current.IOHelper.BackOfficePath.EnsureEndsWith("/"), Icon);
+                var backOfficePath = Current.Configs.Global().GetUmbracoMvcArea(Current.HostingEnvironment);
+                return string.Format("{0}images/umbraco/{1}", backOfficePath.EnsureEndsWith("/"), Icon);
             }
         }
 
diff --git a/src/Umbraco.Infrastructure/WebAssets/BackOfficeJavaScriptInitializer.cs b/src/Umbraco.Infrastructure/WebAssets/BackOfficeJavaScriptInitializer.cs
index 64de289549..18279e35ba 100644
--- a/src/Umbraco.Infrastructure/WebAssets/BackOfficeJavaScriptInitializer.cs
+++ b/src/Umbraco.Infrastructure/WebAssets/BackOfficeJavaScriptInitializer.cs
@@ -2,6 +2,7 @@
 using System.Text;
 using System.Text.RegularExpressions;
 using Umbraco.Core.Configuration;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.IO;
 
 namespace Umbraco.Web.WebAssets
@@ -28,9 +29,9 @@ namespace Umbraco.Web.WebAssets
         /// The angular module name to boot
         /// </param>
         /// <param name="globalSettings"></param>
-        /// <param name="ioHelper"></param>
+        /// <param name="hostingEnvironment"></param>
         /// <returns></returns>
-        public static string GetJavascriptInitialization(IEnumerable<string> scripts, string angularModule, IGlobalSettings globalSettings, IIOHelper ioHelper)
+        public static string GetJavascriptInitialization(IEnumerable<string> scripts, string angularModule, IGlobalSettings globalSettings, IHostingEnvironment hostingEnvironment)
         {
             var jarray = new StringBuilder();
             jarray.AppendLine("[");
@@ -46,7 +47,7 @@ namespace Umbraco.Web.WebAssets
             }
             jarray.Append("]");
 
-            return WriteScript(jarray.ToString(), ioHelper.ResolveUrl(globalSettings.UmbracoPath), angularModule);
+            return WriteScript(jarray.ToString(), hostingEnvironment.ToAbsolute(globalSettings.UmbracoPath), angularModule);
         }
 
         /// <summary>
diff --git a/src/Umbraco.Infrastructure/WebAssets/BackOfficeWebAssets.cs b/src/Umbraco.Infrastructure/WebAssets/BackOfficeWebAssets.cs
index 612e3d6b53..fcb27f7189 100644
--- a/src/Umbraco.Infrastructure/WebAssets/BackOfficeWebAssets.cs
+++ b/src/Umbraco.Infrastructure/WebAssets/BackOfficeWebAssets.cs
@@ -4,6 +4,7 @@ using System.Linq;
 using Newtonsoft.Json;
 using Newtonsoft.Json.Linq;
 using Umbraco.Core;
+using Umbraco.Core.Configuration;
 using Umbraco.Core.Hosting;
 using Umbraco.Core.IO;
 using Umbraco.Core.Manifest;
@@ -24,19 +25,22 @@ namespace Umbraco.Web.WebAssets
 
         private readonly IRuntimeMinifier _runtimeMinifier;
         private readonly IManifestParser _parser;
-        private readonly IIOHelper _ioHelper;
+        private readonly IGlobalSettings _globalSettings;
+        private readonly IHostingEnvironment _hostingEnvironment;
         private readonly PropertyEditorCollection _propertyEditorCollection;
 
         public BackOfficeWebAssets(
             IRuntimeMinifier runtimeMinifier,
             IManifestParser parser,
-            IIOHelper ioHelper,
-            PropertyEditorCollection propertyEditorCollection)
+            PropertyEditorCollection propertyEditorCollection,
+            IHostingEnvironment hostingEnvironment,
+            IGlobalSettings globalSettings)
         {
             _runtimeMinifier = runtimeMinifier;
             _parser = parser;
-            _ioHelper = ioHelper;
             _propertyEditorCollection = propertyEditorCollection;
+            _hostingEnvironment = hostingEnvironment;
+            _globalSettings = globalSettings;
         }
 
         public void CreateBundles()
@@ -150,7 +154,7 @@ namespace Umbraco.Web.WebAssets
         /// <returns></returns>
         private string[] FormatPaths(params string[] assets)
         {
-            var umbracoPath = _ioHelper.GetUmbracoMvcArea();
+            var umbracoPath = _globalSettings.GetUmbracoMvcArea(_hostingEnvironment);
 
             return assets
                 .Where(x => x.IsNullOrWhiteSpace() == false)
diff --git a/src/Umbraco.Infrastructure/WebAssets/RuntimeMinifierExtensions.cs b/src/Umbraco.Infrastructure/WebAssets/RuntimeMinifierExtensions.cs
index a7c9f65668..072afa5816 100644
--- a/src/Umbraco.Infrastructure/WebAssets/RuntimeMinifierExtensions.cs
+++ b/src/Umbraco.Infrastructure/WebAssets/RuntimeMinifierExtensions.cs
@@ -3,6 +3,7 @@ using System.Collections.Generic;
 using System.Text;
 using System.Threading.Tasks;
 using Umbraco.Core.Configuration;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.IO;
 using Umbraco.Core.WebAssets;
 
@@ -14,10 +15,10 @@ namespace Umbraco.Web.WebAssets
         /// Returns the JavaScript to load the back office's assets
         /// </summary>
         /// <returns></returns>
-        public static async Task<string> GetScriptForLoadingBackOfficeAsync(this IRuntimeMinifier minifier, IGlobalSettings globalSettings, IIOHelper ioHelper)
+        public static async Task<string> GetScriptForLoadingBackOfficeAsync(this IRuntimeMinifier minifier, IGlobalSettings globalSettings, IHostingEnvironment hostingEnvironment)
         {
             var files = await minifier.GetAssetPathsAsync(BackOfficeWebAssets.UmbracoJsBundleName);
-            var result = BackOfficeJavaScriptInitializer.GetJavascriptInitialization(files, "umbraco", globalSettings, ioHelper);
+            var result = BackOfficeJavaScriptInitializer.GetJavascriptInitialization(files, "umbraco", globalSettings, hostingEnvironment);
             result += await GetStylesheetInitializationAsync(minifier);
 
             return result;
diff --git a/src/Umbraco.Tests/Cache/DistributedCacheBinderTests.cs b/src/Umbraco.Tests/Cache/DistributedCacheBinderTests.cs
index eedcc498c5..1632944895 100644
--- a/src/Umbraco.Tests/Cache/DistributedCacheBinderTests.cs
+++ b/src/Umbraco.Tests/Cache/DistributedCacheBinderTests.cs
@@ -163,7 +163,7 @@ namespace Umbraco.Tests.Cache
                 new TestDefaultCultureAccessor(),
                 TestObjects.GetGlobalSettings(),
                 Mock.Of<IUserService>(),
-                IOHelper,
+                TestHelper.GetHostingEnvironment(),
                 UriUtility,
                 httpContextAccessor,
                 new AspNetCookieManager(httpContextAccessor));
diff --git a/src/Umbraco.Tests/Cache/PublishedCache/PublishedContentCacheTests.cs b/src/Umbraco.Tests/Cache/PublishedCache/PublishedContentCacheTests.cs
index af4c660112..524a939574 100644
--- a/src/Umbraco.Tests/Cache/PublishedCache/PublishedContentCacheTests.cs
+++ b/src/Umbraco.Tests/Cache/PublishedCache/PublishedContentCacheTests.cs
@@ -79,10 +79,10 @@ namespace Umbraco.Tests.Cache.PublishedCache
             _umbracoContext = new UmbracoContext(
                 httpContextAccessor,
                 publishedSnapshotService.Object,
-                new WebSecurity(httpContextAccessor, Mock.Of<IUserService>(), globalSettings, IOHelper),
+                new WebSecurity(httpContextAccessor, Mock.Of<IUserService>(), globalSettings, HostingEnvironment),
                 globalSettings,
+                HostingEnvironment,
                 new TestVariationContextAccessor(),
-                IOHelper,
                 UriUtility,
                 new AspNetCookieManager(httpContextAccessor));
 
diff --git a/src/Umbraco.Tests/Configurations/GlobalSettingsTests.cs b/src/Umbraco.Tests/Configurations/GlobalSettingsTests.cs
index a1f1e6a66d..327c801f5b 100644
--- a/src/Umbraco.Tests/Configurations/GlobalSettingsTests.cs
+++ b/src/Umbraco.Tests/Configurations/GlobalSettingsTests.cs
@@ -3,6 +3,7 @@ using NUnit.Framework;
 using Umbraco.Core.Configuration;
 using Umbraco.Core.IO;
 using Umbraco.Tests.TestHelpers;
+using Umbraco.Web.Hosting;
 
 namespace Umbraco.Tests.Configurations
 {
@@ -10,20 +11,6 @@ namespace Umbraco.Tests.Configurations
     [TestFixture]
     public class GlobalSettingsTests : BaseWebTest
     {
-        private string _root;
-
-        public override void SetUp()
-        {
-            base.SetUp();
-            _root = TestHelper.IOHelper.Root;
-        }
-
-        public override void TearDown()
-        {
-            base.TearDown();
-            TestHelper.IOHelper.Root = _root;
-        }
-
         [TestCase("~/umbraco", "/", "umbraco")]
         [TestCase("~/umbraco", "/MyVirtualDir", "umbraco")]
         [TestCase("~/customPath", "/MyVirtualDir/", "custompath")]
@@ -33,18 +20,15 @@ namespace Umbraco.Tests.Configurations
         {
 
             var globalSettings = SettingsForTests.GenerateMockGlobalSettings();
-            var ioHelper = new IOHelper(TestHelper.GetHostingEnvironment(), globalSettings);
+            var mockHostingSettings = Mock.Get(SettingsForTests.GetDefaultHostingSettings());
+            mockHostingSettings.Setup(x => x.ApplicationVirtualPath).Returns(rootPath);
+
+            var hostingEnvironment = new AspNetHostingEnvironment(mockHostingSettings.Object);
 
             var globalSettingsMock = Mock.Get(globalSettings);
             globalSettingsMock.Setup(x => x.UmbracoPath).Returns(() => path);
 
-            ioHelper.Root = rootPath;
-            Assert.AreEqual(outcome, ioHelper.GetUmbracoMvcAreaNoCache());
+            Assert.AreEqual(outcome, globalSettingsMock.Object.GetUmbracoMvcAreaNoCache(hostingEnvironment));
         }
-
-
-
-
-
     }
 }
diff --git a/src/Umbraco.Tests/CoreThings/UriExtensionsTests.cs b/src/Umbraco.Tests/CoreThings/UriExtensionsTests.cs
index 2fda471b70..1fe3a50d0c 100644
--- a/src/Umbraco.Tests/CoreThings/UriExtensionsTests.cs
+++ b/src/Umbraco.Tests/CoreThings/UriExtensionsTests.cs
@@ -1,28 +1,17 @@
 using System;
+using Moq;
 using NUnit.Framework;
 using Umbraco.Core;
 using Umbraco.Core.Composing;
 using Umbraco.Core.IO;
 using Umbraco.Tests.TestHelpers;
+using Umbraco.Web.Hosting;
 
 namespace Umbraco.Tests.CoreThings
 {
     [TestFixture]
     public class UriExtensionsTests
     {
-        private string _root;
-
-        [SetUp]
-        public void SetUp()
-        {
-            _root = TestHelper.IOHelper.Root;
-        }
-
-        [TearDown]
-        public void TearDown()
-        {
-            TestHelper.IOHelper.Root = _root;
-        }
 
         [TestCase("http://www.domain.com/umbraco", "", true)]
         [TestCase("http://www.domain.com/Umbraco/", "", true)]
@@ -45,10 +34,13 @@ namespace Umbraco.Tests.CoreThings
         [TestCase("http://www.domain.com/umbraco/test/legacyAjaxCalls.ashx?some=query&blah=js", "", true)]
         public void Is_Back_Office_Request(string input, string virtualPath, bool expected)
         {
-            var ioHelper = TestHelper.IOHelper;
-            ioHelper.Root = virtualPath;
+            var globalSettings = SettingsForTests.GenerateMockGlobalSettings();
+            var mockHostingSettings = Mock.Get(SettingsForTests.GetDefaultHostingSettings());
+            mockHostingSettings.Setup(x => x.ApplicationVirtualPath).Returns(virtualPath);
+            var hostingEnvironment = new AspNetHostingEnvironment(mockHostingSettings.Object);
+
             var source = new Uri(input);
-            Assert.AreEqual(expected, source.IsBackOfficeRequest(virtualPath, ioHelper));
+            Assert.AreEqual(expected, source.IsBackOfficeRequest(globalSettings, hostingEnvironment));
         }
 
         [TestCase("http://www.domain.com/install", true)]
@@ -63,7 +55,7 @@ namespace Umbraco.Tests.CoreThings
         public void Is_Installer_Request(string input, bool expected)
         {
             var source = new Uri(input);
-            Assert.AreEqual(expected, source.IsInstallerRequest(TestHelper.IOHelper));
+            Assert.AreEqual(expected, source.IsInstallerRequest(TestHelper.GetHostingEnvironment()));
         }
 
         [TestCase("http://www.domain.com/foo/bar", "/", "http://www.domain.com/")]
diff --git a/src/Umbraco.Tests/PublishedContent/PublishedContentSnapshotTestBase.cs b/src/Umbraco.Tests/PublishedContent/PublishedContentSnapshotTestBase.cs
index 756f452f71..02d380d843 100644
--- a/src/Umbraco.Tests/PublishedContent/PublishedContentSnapshotTestBase.cs
+++ b/src/Umbraco.Tests/PublishedContent/PublishedContentSnapshotTestBase.cs
@@ -74,10 +74,10 @@ namespace Umbraco.Tests.PublishedContent
             var umbracoContext = new UmbracoContext(
                 httpContextAccessor,
                 publishedSnapshotService.Object,
-                new WebSecurity(httpContextAccessor, ServiceContext.UserService, globalSettings, IOHelper),
+                new WebSecurity(httpContextAccessor, ServiceContext.UserService, globalSettings, HostingEnvironment),
                 globalSettings,
+                HostingEnvironment,
                 new TestVariationContextAccessor(),
-                IOHelper,
                 UriUtility,
                 new AspNetCookieManager(httpContextAccessor));
 
diff --git a/src/Umbraco.Tests/Routing/RenderRouteHandlerTests.cs b/src/Umbraco.Tests/Routing/RenderRouteHandlerTests.cs
index bc58282795..b900453a5e 100644
--- a/src/Umbraco.Tests/Routing/RenderRouteHandlerTests.cs
+++ b/src/Umbraco.Tests/Routing/RenderRouteHandlerTests.cs
@@ -44,7 +44,7 @@ namespace Umbraco.Tests.Routing
                 ShortStringHelper,
                 new SurfaceControllerTypeCollection(Enumerable.Empty<Type>()),
                 new UmbracoApiControllerTypeCollection(Enumerable.Empty<Type>()),
-                IOHelper);
+                HostingEnvironment);
         }
 
         public class TestRuntime : WebRuntime
diff --git a/src/Umbraco.Tests/Routing/UmbracoModuleTests.cs b/src/Umbraco.Tests/Routing/UmbracoModuleTests.cs
index f9de3579c2..2e83427b07 100644
--- a/src/Umbraco.Tests/Routing/UmbracoModuleTests.cs
+++ b/src/Umbraco.Tests/Routing/UmbracoModuleTests.cs
@@ -43,7 +43,8 @@ namespace Umbraco.Tests.Routing
                 new RoutableDocumentFilter(globalSettings, IOHelper),
                 UriUtility,
                 AppCaches.RequestCache,
-                IOHelper
+                globalSettings,
+                HostingEnvironment
             );
 
             runtime.Level = RuntimeLevel.Run;
diff --git a/src/Umbraco.Tests/Runtimes/WebRuntimeComponentTests.cs b/src/Umbraco.Tests/Runtimes/WebRuntimeComponentTests.cs
index c03fe04a2d..42a0eeba54 100644
--- a/src/Umbraco.Tests/Runtimes/WebRuntimeComponentTests.cs
+++ b/src/Umbraco.Tests/Runtimes/WebRuntimeComponentTests.cs
@@ -16,7 +16,7 @@ namespace Umbraco.Tests.Runtimes
         {
             IList<IViewEngine> engines = new List<IViewEngine>
                 {
-                    new RenderViewEngine(TestHelper.IOHelper),
+                    new RenderViewEngine(TestHelper.GetHostingEnvironment()),
                     new PluginViewEngine()
                 };
 
@@ -32,7 +32,7 @@ namespace Umbraco.Tests.Runtimes
         {
             IList<IViewEngine> engines = new List<IViewEngine>
                 {
-                    new RenderViewEngine(TestHelper.IOHelper),
+                    new RenderViewEngine(TestHelper.GetHostingEnvironment()),
                     new PluginViewEngine()
                 };
 
diff --git a/src/Umbraco.Tests/Scoping/ScopedNuCacheTests.cs b/src/Umbraco.Tests/Scoping/ScopedNuCacheTests.cs
index 8603d901c2..0113237486 100644
--- a/src/Umbraco.Tests/Scoping/ScopedNuCacheTests.cs
+++ b/src/Umbraco.Tests/Scoping/ScopedNuCacheTests.cs
@@ -123,10 +123,10 @@ namespace Umbraco.Tests.Scoping
             var umbracoContext = new UmbracoContext(
                 httpContextAccessor,
                 service,
-                new WebSecurity(httpContextAccessor, ServiceContext.UserService, globalSettings, IOHelper),
+                new WebSecurity(httpContextAccessor, ServiceContext.UserService, globalSettings, HostingEnvironment),
                 globalSettings,
+                HostingEnvironment,
                 new TestVariationContextAccessor(),
-                IOHelper,
                 UriUtility,
                 new AspNetCookieManager(httpContextAccessor));
 
diff --git a/src/Umbraco.Tests/Security/BackOfficeCookieManagerTests.cs b/src/Umbraco.Tests/Security/BackOfficeCookieManagerTests.cs
index 8b84579fec..988dfb178d 100644
--- a/src/Umbraco.Tests/Security/BackOfficeCookieManagerTests.cs
+++ b/src/Umbraco.Tests/Security/BackOfficeCookieManagerTests.cs
@@ -34,15 +34,16 @@ namespace Umbraco.Tests.Security
             var umbracoContext = new UmbracoContext(
                 httpContextAccessor,
                 Mock.Of<IPublishedSnapshotService>(),
-                new WebSecurity(httpContextAccessor, ServiceContext.UserService, globalSettings, IOHelper), globalSettings,
+                new WebSecurity(httpContextAccessor, ServiceContext.UserService, globalSettings, HostingEnvironment),
+                globalSettings,
+                HostingEnvironment,
                 new TestVariationContextAccessor(),
-                IOHelper,
                 UriUtility,
                 new AspNetCookieManager(httpContextAccessor));
 
             var runtime = Mock.Of<IRuntimeState>(x => x.Level == RuntimeLevel.Install);
             var mgr = new BackOfficeCookieManager(
-                Mock.Of<IUmbracoContextAccessor>(accessor => accessor.UmbracoContext == umbracoContext), runtime,  IOHelper, AppCaches.RequestCache);
+                Mock.Of<IUmbracoContextAccessor>(accessor => accessor.UmbracoContext == umbracoContext), runtime, HostingEnvironment, globalSettings, AppCaches.RequestCache);
 
             var result = mgr.ShouldAuthenticateRequest(Mock.Of<IOwinContext>(), new Uri("http://localhost/umbraco"));
 
@@ -57,15 +58,15 @@ namespace Umbraco.Tests.Security
             var umbCtx = new UmbracoContext(
                 httpContextAccessor,
                 Mock.Of<IPublishedSnapshotService>(),
-                new WebSecurity(httpContextAccessor, ServiceContext.UserService, globalSettings, IOHelper),
+                new WebSecurity(httpContextAccessor, ServiceContext.UserService, globalSettings, HostingEnvironment),
                 globalSettings,
+                HostingEnvironment,
                 new TestVariationContextAccessor(),
-                IOHelper,
                 UriUtility,
                 new AspNetCookieManager(httpContextAccessor));
 
             var runtime = Mock.Of<IRuntimeState>(x => x.Level == RuntimeLevel.Run);
-            var mgr = new BackOfficeCookieManager(Mock.Of<IUmbracoContextAccessor>(accessor => accessor.UmbracoContext == umbCtx), runtime,  IOHelper, AppCaches.RequestCache);
+            var mgr = new BackOfficeCookieManager(Mock.Of<IUmbracoContextAccessor>(accessor => accessor.UmbracoContext == umbCtx), runtime, HostingEnvironment, globalSettings, AppCaches.RequestCache);
 
             var request = new Mock<OwinRequest>();
             request.Setup(owinRequest => owinRequest.Uri).Returns(new Uri("http://localhost/umbraco"));
diff --git a/src/Umbraco.Tests/TestHelpers/ControllerTesting/TestControllerActivatorBase.cs b/src/Umbraco.Tests/TestHelpers/ControllerTesting/TestControllerActivatorBase.cs
index a39219a570..66310caea9 100644
--- a/src/Umbraco.Tests/TestHelpers/ControllerTesting/TestControllerActivatorBase.cs
+++ b/src/Umbraco.Tests/TestHelpers/ControllerTesting/TestControllerActivatorBase.cs
@@ -143,8 +143,8 @@ namespace Umbraco.Tests.TestHelpers.ControllerTesting
                 publishedSnapshotService.Object,
                 webSecurity.Object,
                 globalSettings,
+                TestHelper.GetHostingEnvironment(),
                 new TestVariationContextAccessor(),
-                TestHelper.IOHelper,
                 TestHelper.UriUtility,
                 new AspNetCookieManager(httpContextAccessor));
 
diff --git a/src/Umbraco.Tests/TestHelpers/TestObjects-Mocks.cs b/src/Umbraco.Tests/TestHelpers/TestObjects-Mocks.cs
index 49444f8b68..585ad6cc9e 100644
--- a/src/Umbraco.Tests/TestHelpers/TestObjects-Mocks.cs
+++ b/src/Umbraco.Tests/TestHelpers/TestObjects-Mocks.cs
@@ -127,7 +127,7 @@ namespace Umbraco.Tests.TestHelpers
                 new TestDefaultCultureAccessor(),
                 globalSettings,
                 Mock.Of<IUserService>(),
-                TestHelper.IOHelper,
+                TestHelper.GetHostingEnvironment(),
                 TestHelper.UriUtility,
                 httpContextAccessor,
                 new AspNetCookieManager(httpContextAccessor));
diff --git a/src/Umbraco.Tests/TestHelpers/TestWithDatabaseBase.cs b/src/Umbraco.Tests/TestHelpers/TestWithDatabaseBase.cs
index 159baa5c79..1245e7d59e 100644
--- a/src/Umbraco.Tests/TestHelpers/TestWithDatabaseBase.cs
+++ b/src/Umbraco.Tests/TestHelpers/TestWithDatabaseBase.cs
@@ -378,10 +378,10 @@ namespace Umbraco.Tests.TestHelpers
                 httpContextAccessor,
                 service,
                 new WebSecurity(httpContextAccessor, Factory.GetInstance<IUserService>(),
-                    Factory.GetInstance<IGlobalSettings>(), IOHelper),
+                    Factory.GetInstance<IGlobalSettings>(), HostingEnvironment),
                 globalSettings ?? Factory.GetInstance<IGlobalSettings>(),
+                HostingEnvironment,
                 new TestVariationContextAccessor(),
-                IOHelper,
                 UriUtility,
                 new AspNetCookieManager(httpContextAccessor));
 
diff --git a/src/Umbraco.Tests/Testing/Objects/TestUmbracoContextFactory.cs b/src/Umbraco.Tests/Testing/Objects/TestUmbracoContextFactory.cs
index d6a1606853..cb20c56d6d 100644
--- a/src/Umbraco.Tests/Testing/Objects/TestUmbracoContextFactory.cs
+++ b/src/Umbraco.Tests/Testing/Objects/TestUmbracoContextFactory.cs
@@ -43,7 +43,7 @@ namespace Umbraco.Tests.Testing.Objects
                 new TestDefaultCultureAccessor(),
                 globalSettings,
                 Mock.Of<IUserService>(),
-                TestHelper.IOHelper,
+                TestHelper.GetHostingEnvironment(),
                 TestHelper.UriUtility,
                 httpContextAccessor,
                 new AspNetCookieManager(httpContextAccessor));
diff --git a/src/Umbraco.Tests/Web/Controllers/AuthenticationControllerTests.cs b/src/Umbraco.Tests/Web/Controllers/AuthenticationControllerTests.cs
index 1499c5274e..c09842f730 100644
--- a/src/Umbraco.Tests/Web/Controllers/AuthenticationControllerTests.cs
+++ b/src/Umbraco.Tests/Web/Controllers/AuthenticationControllerTests.cs
@@ -33,6 +33,7 @@ using Umbraco.Web.Features;
 using Umbraco.Web.Models.ContentEditing;
 using IUser = Umbraco.Core.Models.Membership.IUser;
 using Umbraco.Core.Configuration.UmbracoSettings;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.IO;
 using Umbraco.Web.Routing;
 
@@ -81,6 +82,7 @@ namespace Umbraco.Tests.Web.Controllers
                 var usersController = new AuthenticationController(
                     new TestUserPasswordConfig(),
                     Factory.GetInstance<IGlobalSettings>(),
+                    Factory.GetInstance<IHostingEnvironment>(),
                     umbracoContextAccessor,
                     Factory.GetInstance<ISqlContext>(),
                     Factory.GetInstance<ServiceContext>(),
@@ -89,7 +91,6 @@ namespace Umbraco.Tests.Web.Controllers
                     Factory.GetInstance<IRuntimeState>(),
                     Factory.GetInstance<UmbracoMapper>(),
                     Factory.GetInstance<ISecuritySettings>(),
-                    Factory.GetInstance<IIOHelper>(),
                     Factory.GetInstance<IPublishedUrlProvider>()
                     );
                 return usersController;
diff --git a/src/Umbraco.Tests/Web/Controllers/PluginControllerAreaTests.cs b/src/Umbraco.Tests/Web/Controllers/PluginControllerAreaTests.cs
index 23131b04e6..59209f3e7d 100644
--- a/src/Umbraco.Tests/Web/Controllers/PluginControllerAreaTests.cs
+++ b/src/Umbraco.Tests/Web/Controllers/PluginControllerAreaTests.cs
@@ -14,7 +14,7 @@ namespace Umbraco.Tests.Web.Controllers
         public void Ensure_Same_Area1()
         {
             Assert.Throws<InvalidOperationException>(() =>
-                                                     new PluginControllerArea(TestObjects.GetGlobalSettings(), IOHelper,
+                                                     new PluginControllerArea(TestObjects.GetGlobalSettings(), HostingEnvironment,
                                                          new PluginControllerMetadata[]
                                                          {
                                                             PluginController.GetMetadata(typeof(Plugin1Controller)),
@@ -27,7 +27,7 @@ namespace Umbraco.Tests.Web.Controllers
         public void Ensure_Same_Area3()
         {
             Assert.Throws<InvalidOperationException>(() =>
-                                                     new PluginControllerArea(TestObjects.GetGlobalSettings(), IOHelper,
+                                                     new PluginControllerArea(TestObjects.GetGlobalSettings(), HostingEnvironment,
                                                          new PluginControllerMetadata[]
                                                          {
                                                             PluginController.GetMetadata(typeof(Plugin1Controller)),
@@ -39,7 +39,7 @@ namespace Umbraco.Tests.Web.Controllers
         [Test]
         public void Ensure_Same_Area2()
         {
-            var area = new PluginControllerArea(TestObjects.GetGlobalSettings(), IOHelper,
+            var area = new PluginControllerArea(TestObjects.GetGlobalSettings(), HostingEnvironment,
                 new PluginControllerMetadata[]
                 {
                     PluginController.GetMetadata(typeof(Plugin1Controller)),
diff --git a/src/Umbraco.Tests/Web/Controllers/UsersControllerTests.cs b/src/Umbraco.Tests/Web/Controllers/UsersControllerTests.cs
index d6c9385aa9..563d9b80f8 100644
--- a/src/Umbraco.Tests/Web/Controllers/UsersControllerTests.cs
+++ b/src/Umbraco.Tests/Web/Controllers/UsersControllerTests.cs
@@ -36,6 +36,7 @@ using Umbraco.Web.Models.ContentEditing;
 using IUser = Umbraco.Core.Models.Membership.IUser;
 using Umbraco.Core.Mapping;
 using Umbraco.Core.Configuration.UmbracoSettings;
+using Umbraco.Core.Hosting;
 using Umbraco.Web.Routing;
 using Umbraco.Core.Media;
 
@@ -91,7 +92,7 @@ namespace Umbraco.Tests.Web.Controllers
                     ShortStringHelper,
                     Factory.GetInstance<UmbracoMapper>(),
                     Factory.GetInstance<IContentSettings>(),
-                    Factory.GetInstance<IIOHelper>(),
+                    Factory.GetInstance<IHostingEnvironment>(),
                     Factory.GetInstance<IImageUrlGenerator>(),
                     Factory.GetInstance<IPublishedUrlProvider>(),
                     Factory.GetInstance<ISecuritySettings>()
@@ -164,7 +165,7 @@ namespace Umbraco.Tests.Web.Controllers
                     ShortStringHelper,
                     Factory.GetInstance<UmbracoMapper>(),
                     Factory.GetInstance<IContentSettings>(),
-                    Factory.GetInstance<IIOHelper>(),
+                    Factory.GetInstance<IHostingEnvironment>(),
                     Factory.GetInstance<IImageUrlGenerator>(),
                     Factory.GetInstance<IPublishedUrlProvider>(),
                     Factory.GetInstance<ISecuritySettings>()
@@ -207,7 +208,7 @@ namespace Umbraco.Tests.Web.Controllers
                     ShortStringHelper,
                     Factory.GetInstance<UmbracoMapper>(),
                     Factory.GetInstance<IContentSettings>(),
-                    Factory.GetInstance<IIOHelper>(),
+                    Factory.GetInstance<IHostingEnvironment>(),
                     Factory.GetInstance<IImageUrlGenerator>(),
                     Factory.GetInstance<IPublishedUrlProvider>(),
                     Factory.GetInstance<ISecuritySettings>()
@@ -285,7 +286,7 @@ namespace Umbraco.Tests.Web.Controllers
                     ShortStringHelper,
                     Factory.GetInstance<UmbracoMapper>(),
                     Factory.GetInstance<IContentSettings>(),
-                    Factory.GetInstance<IIOHelper>(),
+                    Factory.GetInstance<IHostingEnvironment>(),
                     Factory.GetInstance<IImageUrlGenerator>(),
                     Factory.GetInstance<IPublishedUrlProvider>(),
                     Factory.GetInstance<ISecuritySettings>()
diff --git a/src/Umbraco.Tests/Web/Mvc/RenderIndexActionSelectorAttributeTests.cs b/src/Umbraco.Tests/Web/Mvc/RenderIndexActionSelectorAttributeTests.cs
index 7906047520..bd9b646872 100644
--- a/src/Umbraco.Tests/Web/Mvc/RenderIndexActionSelectorAttributeTests.cs
+++ b/src/Umbraco.Tests/Web/Mvc/RenderIndexActionSelectorAttributeTests.cs
@@ -72,7 +72,7 @@ namespace Umbraco.Tests.Web.Mvc
                 new TestDefaultCultureAccessor(),
                 globalSettings,
                 Mock.Of<IUserService>(),
-                TestHelper.IOHelper,
+                TestHelper.GetHostingEnvironment(),
                 TestHelper.UriUtility,
                 httpContextAccessor,
                 new AspNetCookieManager(httpContextAccessor));
@@ -104,7 +104,7 @@ namespace Umbraco.Tests.Web.Mvc
                 new TestDefaultCultureAccessor(),
                 globalSettings,
                 Mock.Of<IUserService>(),
-                TestHelper.IOHelper,
+                TestHelper.GetHostingEnvironment(),
                 TestHelper.UriUtility,
                 httpContextAccessor,
                 new AspNetCookieManager(httpContextAccessor));
@@ -136,7 +136,7 @@ namespace Umbraco.Tests.Web.Mvc
                 new TestDefaultCultureAccessor(),
                 globalSettings,
                 Mock.Of<IUserService>(),
-                TestHelper.IOHelper,
+                TestHelper.GetHostingEnvironment(),
                 TestHelper.UriUtility,
                 httpContextAccessor,
                 new AspNetCookieManager(httpContextAccessor));
@@ -168,7 +168,7 @@ namespace Umbraco.Tests.Web.Mvc
                 new TestDefaultCultureAccessor(),
                 globalSettings,
                 Mock.Of<IUserService>(),
-                TestHelper.IOHelper,
+                TestHelper.GetHostingEnvironment(),
                 TestHelper.UriUtility,
                 httpContextAccessor,
                 new AspNetCookieManager(httpContextAccessor));
diff --git a/src/Umbraco.Tests/Web/Mvc/SurfaceControllerTests.cs b/src/Umbraco.Tests/Web/Mvc/SurfaceControllerTests.cs
index 2a9b85aba5..4c222b9116 100644
--- a/src/Umbraco.Tests/Web/Mvc/SurfaceControllerTests.cs
+++ b/src/Umbraco.Tests/Web/Mvc/SurfaceControllerTests.cs
@@ -47,7 +47,7 @@ namespace Umbraco.Tests.Web.Mvc
                 new TestDefaultCultureAccessor(),
                 globalSettings,
                 Mock.Of<IUserService>(),
-                IOHelper,
+                HostingEnvironment,
                 UriUtility,
                 httpContextAccessor,
                 new AspNetCookieManager(httpContextAccessor));
@@ -77,7 +77,7 @@ namespace Umbraco.Tests.Web.Mvc
                 new TestDefaultCultureAccessor(),
                 globalSettings,
                 Mock.Of<IUserService>(),
-                IOHelper,
+                HostingEnvironment,
                 UriUtility,
                 httpContextAccessor,
                 new AspNetCookieManager(httpContextAccessor));
@@ -110,7 +110,7 @@ namespace Umbraco.Tests.Web.Mvc
                 new TestDefaultCultureAccessor(),
                 globalSettings,
                 Mock.Of<IUserService>(),
-                IOHelper,
+                HostingEnvironment,
                 UriUtility,
                 httpContextAccessor,
                 new AspNetCookieManager(httpContextAccessor));
@@ -143,7 +143,7 @@ namespace Umbraco.Tests.Web.Mvc
                 new TestDefaultCultureAccessor(),
                 globalSettings,
                 Mock.Of<IUserService>(),
-                IOHelper,
+                HostingEnvironment,
                 UriUtility,
                 httpContextAccessor,
                 new AspNetCookieManager(httpContextAccessor));
diff --git a/src/Umbraco.Tests/Web/Mvc/UmbracoViewPageTests.cs b/src/Umbraco.Tests/Web/Mvc/UmbracoViewPageTests.cs
index c5e9556d05..dbe45ccd29 100644
--- a/src/Umbraco.Tests/Web/Mvc/UmbracoViewPageTests.cs
+++ b/src/Umbraco.Tests/Web/Mvc/UmbracoViewPageTests.cs
@@ -438,10 +438,10 @@ namespace Umbraco.Tests.Web.Mvc
             var ctx = new UmbracoContext(
                 httpContextAccessor,
                 _service,
-                new WebSecurity(httpContextAccessor, ServiceContext.UserService, globalSettings, IOHelper),
+                new WebSecurity(httpContextAccessor, ServiceContext.UserService, globalSettings, HostingEnvironment),
                 globalSettings,
+                HostingEnvironment,
                 new TestVariationContextAccessor(),
-                IOHelper,
                 UriUtility,
                 new AspNetCookieManager(httpContextAccessor));
 
diff --git a/src/Umbraco.Tests/Web/WebExtensionMethodTests.cs b/src/Umbraco.Tests/Web/WebExtensionMethodTests.cs
index 123c5d3f62..a9610c6de2 100644
--- a/src/Umbraco.Tests/Web/WebExtensionMethodTests.cs
+++ b/src/Umbraco.Tests/Web/WebExtensionMethodTests.cs
@@ -32,10 +32,10 @@ namespace Umbraco.Tests.Web
             var umbCtx = new UmbracoContext(
                 httpContextAccessor,
                 Mock.Of<IPublishedSnapshotService>(),
-                new WebSecurity(httpContextAccessor, ServiceContext.UserService, TestObjects.GetGlobalSettings(), IOHelper),
+                new WebSecurity(httpContextAccessor, ServiceContext.UserService, TestObjects.GetGlobalSettings(), HostingEnvironment),
                 TestObjects.GetGlobalSettings(),
+                HostingEnvironment,
                 new TestVariationContextAccessor(),
-                IOHelper,
                 UriUtility,
                 new AspNetCookieManager(httpContextAccessor));
             var r1 = new RouteData();
@@ -53,10 +53,10 @@ namespace Umbraco.Tests.Web
             var umbCtx = new UmbracoContext(
                 httpContextAccessor,
                 Mock.Of<IPublishedSnapshotService>(),
-                new WebSecurity(httpContextAccessor, ServiceContext.UserService, TestObjects.GetGlobalSettings(), IOHelper),
+                new WebSecurity(httpContextAccessor, ServiceContext.UserService, TestObjects.GetGlobalSettings(), HostingEnvironment),
                 TestObjects.GetGlobalSettings(),
+                HostingEnvironment,
                 new TestVariationContextAccessor(),
-                IOHelper,
                 UriUtility,
                 new AspNetCookieManager(httpContextAccessor));
 
@@ -84,10 +84,10 @@ namespace Umbraco.Tests.Web
             var umbCtx = new UmbracoContext(
                 httpContextAccessor,
                 Mock.Of<IPublishedSnapshotService>(),
-                new WebSecurity(httpContextAccessor, ServiceContext.UserService, TestObjects.GetGlobalSettings(), IOHelper),
+                new WebSecurity(httpContextAccessor, ServiceContext.UserService, TestObjects.GetGlobalSettings(), HostingEnvironment),
                 TestObjects.GetGlobalSettings(),
+                HostingEnvironment,
                 new TestVariationContextAccessor(),
-                IOHelper,
                 UriUtility,
                 new AspNetCookieManager(httpContextAccessor));
 
diff --git a/src/Umbraco.Web.BackOffice/Controllers/BackOfficeController.cs b/src/Umbraco.Web.BackOffice/Controllers/BackOfficeController.cs
index 5c65b638c5..79612fec45 100644
--- a/src/Umbraco.Web.BackOffice/Controllers/BackOfficeController.cs
+++ b/src/Umbraco.Web.BackOffice/Controllers/BackOfficeController.cs
@@ -1,6 +1,7 @@
 using System.Threading.Tasks;
 using Microsoft.AspNetCore.Mvc;
 using Umbraco.Core.Configuration;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.IO;
 using Umbraco.Core.Runtime;
 using Umbraco.Core.WebAssets;
@@ -14,13 +15,13 @@ namespace Umbraco.Web.BackOffice.Controllers
     {
         private readonly IRuntimeMinifier _runtimeMinifier;
         private readonly IGlobalSettings _globalSettings;
-        private readonly IIOHelper _ioHelper;
+        private readonly IHostingEnvironment _hostingEnvironment;
 
-        public BackOfficeController(IRuntimeMinifier runtimeMinifier, IGlobalSettings globalSettings, IIOHelper ioHelper)
+        public BackOfficeController(IRuntimeMinifier runtimeMinifier, IGlobalSettings globalSettings, IHostingEnvironment hostingEnvironment)
         {
             _runtimeMinifier = runtimeMinifier;
             _globalSettings = globalSettings;
-            _ioHelper = ioHelper;
+            _hostingEnvironment = hostingEnvironment;
         }
 
         // GET
@@ -36,7 +37,7 @@ namespace Umbraco.Web.BackOffice.Controllers
         [MinifyJavaScriptResult(Order = 0)]
         public async Task<IActionResult> Application()
         {
-            var result = await _runtimeMinifier.GetScriptForLoadingBackOfficeAsync(_globalSettings, _ioHelper);
+            var result = await _runtimeMinifier.GetScriptForLoadingBackOfficeAsync(_globalSettings, _hostingEnvironment);
 
             return new JavaScriptResult(result);
         }
diff --git a/src/Umbraco.Web.Common/AspNetCore/AspNetCoreHostingEnvironment.cs b/src/Umbraco.Web.Common/AspNetCore/AspNetCoreHostingEnvironment.cs
index e22e4871c8..9344901273 100644
--- a/src/Umbraco.Web.Common/AspNetCore/AspNetCoreHostingEnvironment.cs
+++ b/src/Umbraco.Web.Common/AspNetCore/AspNetCoreHostingEnvironment.cs
@@ -91,13 +91,11 @@ namespace Umbraco.Web.Common.AspNetCore
             if (!virtualPath.StartsWith("~/") && !virtualPath.StartsWith("/"))
                 throw new InvalidOperationException($"{nameof(virtualPath)} must start with ~/ or /");
 
-            var root = ApplicationVirtualPath.EnsureStartsWith('/');
-            
             // will occur if it starts with "/"
             if (Uri.IsWellFormedUriString(virtualPath, UriKind.Absolute))
                 return virtualPath;
 
-            var fullPath = root.EnsureEndsWith('/') + virtualPath.TrimStart("~/");
+            var fullPath = ApplicationVirtualPath.EnsureEndsWith('/') + virtualPath.TrimStart("~/");
 
             return fullPath;
         }
diff --git a/src/Umbraco.Web.UI/Umbraco/Views/AuthorizeUpgrade.cshtml b/src/Umbraco.Web.UI/Umbraco/Views/AuthorizeUpgrade.cshtml
index 8321256d0a..7984bf14f7 100644
--- a/src/Umbraco.Web.UI/Umbraco/Views/AuthorizeUpgrade.cshtml
+++ b/src/Umbraco.Web.UI/Umbraco/Views/AuthorizeUpgrade.cshtml
@@ -14,7 +14,7 @@
 
 <html lang="en">
 <head>
-    <base href="@Model.IOHelper.BackOfficePath.EnsureEndsWith('/')" />
+    <base href="@Model.BackOfficePath.EnsureEndsWith('/')" />
     <meta charset="utf-8">
     <meta name="viewport" content="width=device-width, initial-scale=1.0">
 
@@ -44,9 +44,10 @@
             redirectUrl = Url.Action("AuthorizeUpgrade", "BackOffice")
         });
     }
-    @Html.BareMinimumServerVariablesScript(Url, externalLoginUrl, Model.Features, Model.GlobalSettings, Model.UmbracoVersion, Model.ContentSettings, Model.IOHelper, Model.TreeCollection, Model.HttpContextAccessor, Model.HostingEnvironment, Model.RuntimeSettings, Model.SecuritySettings, runtimeMinifier)
 
-    <script type="text/javascript">
+@Html.BareMinimumServerVariablesScript(Url, Model.Features, Model.GlobalSettings, Model.UmbracoVersion, Model.ContentSettings, Model.TreeCollection, Model.HttpContextAccessor, Model.HostingEnvironment, Model.RuntimeSettings, Model.SecuritySettings, runtimeMinifier)
+
+<script type="text/javascript">
     document.angularReady = function (app) {
 
         @Html.AngularValueExternalLoginInfoScript(ViewData.GetExternalSignInError())
diff --git a/src/Umbraco.Web.UI/Umbraco/Views/Default.cshtml b/src/Umbraco.Web.UI/Umbraco/Views/Default.cshtml
index 135d01755f..a150e0c7e3 100644
--- a/src/Umbraco.Web.UI/Umbraco/Views/Default.cshtml
+++ b/src/Umbraco.Web.UI/Umbraco/Views/Default.cshtml
@@ -105,9 +105,9 @@
                on-login="hideLoginScreen()">
     </umb-login>
 
-    @Html.BareMinimumServerVariablesScript(Url, Url.Action("ExternalLogin", "BackOffice", new { area = ViewData.GetUmbracoPath() }), Model.Features, Model.GlobalSettings, Model.UmbracoVersion, Model.ContentSettings, Model.IOHelper, Model.TreeCollection, Model.HttpContextAccessor, Model.HostingEnvironment, Model.RuntimeSettings, Model.SecuritySettings, Current.RuntimeMinifier)
+@Html.BareMinimumServerVariablesScript(Url, Model.Features, Model.GlobalSettings, Model.UmbracoVersion, Model.ContentSettings, Model.TreeCollection, Model.HttpContextAccessor, Model.HostingEnvironment, Model.RuntimeSettings, Model.SecuritySettings, Current.RuntimeMinifier)
 
-    <script>
+<script>
 
         document.angularReady = function(app) {
             @Html.AngularValueExternalLoginInfoScript(ViewData.GetExternalSignInError())
diff --git a/src/Umbraco.Web/AppBuilderExtensions.cs b/src/Umbraco.Web/AppBuilderExtensions.cs
index e9833e4379..c8c6cbdf5c 100644
--- a/src/Umbraco.Web/AppBuilderExtensions.cs
+++ b/src/Umbraco.Web/AppBuilderExtensions.cs
@@ -3,6 +3,7 @@ using Microsoft.AspNet.SignalR;
 using Microsoft.Owin.Logging;
 using Owin;
 using Umbraco.Core.Configuration;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.IO;
 using Umbraco.Web.Composing;
 using Umbraco.Web.Logging;
@@ -43,10 +44,11 @@ namespace Umbraco.Web
         /// Configures SignalR.
         /// </summary>
         /// <param name="app">The app builder.</param>
-        /// <param name="ioHelper"></param>
-        public static IAppBuilder UseSignalR(this IAppBuilder app, IIOHelper ioHelper)
+        /// <param name="globalSettings"></param>
+        /// <param name="hostingEnvironment"></param>
+        public static IAppBuilder UseSignalR(this IAppBuilder app, IGlobalSettings globalSettings, IHostingEnvironment hostingEnvironment)
         {
-            var umbracoPath = ioHelper.GetUmbracoMvcArea();
+            var umbracoPath = globalSettings.GetUmbracoMvcArea(hostingEnvironment);
             var signalrPath = HttpRuntime.AppDomainAppVirtualPath + umbracoPath + "/BackOffice/signalr";
             return app.MapSignalR(signalrPath, new HubConfiguration { EnableDetailedErrors = true });
         }
diff --git a/src/Umbraco.Web/AspNet/AspNetHostingEnvironment.cs b/src/Umbraco.Web/AspNet/AspNetHostingEnvironment.cs
index bf9d344e9a..b9791b99dd 100644
--- a/src/Umbraco.Web/AspNet/AspNetHostingEnvironment.cs
+++ b/src/Umbraco.Web/AspNet/AspNetHostingEnvironment.cs
@@ -21,7 +21,7 @@ namespace Umbraco.Web.Hosting
             ApplicationId = HostingEnvironment.ApplicationID;
             // when we are not hosted (i.e. unit test or otherwise) we'll need to get the root path from the executing assembly
             ApplicationPhysicalPath = HostingEnvironment.ApplicationPhysicalPath ?? Assembly.GetExecutingAssembly().GetRootDirectorySafe();
-            ApplicationVirtualPath = HostingEnvironment.ApplicationVirtualPath;
+            ApplicationVirtualPath = hostingSettings.ApplicationVirtualPath ?? HostingEnvironment.ApplicationVirtualPath.EnsureStartsWith("/");
             IISVersion = HttpRuntime.IISVersion;
         }
 
@@ -41,7 +41,7 @@ namespace Umbraco.Web.Hosting
             return HostingEnvironment.MapPath(path);
         }
 
-        public string ToAbsolute(string virtualPath) => VirtualPathUtility.ToAbsolute(virtualPath, ApplicationVirtualPath.EnsureStartsWith('/'));
+        public string ToAbsolute(string virtualPath) => VirtualPathUtility.ToAbsolute(virtualPath, ApplicationVirtualPath);
         
 
         public string LocalTempPath
diff --git a/src/Umbraco.Web/Editors/AuthenticationController.cs b/src/Umbraco.Web/Editors/AuthenticationController.cs
index 6519cf4cf6..29a13ea6aa 100644
--- a/src/Umbraco.Web/Editors/AuthenticationController.cs
+++ b/src/Umbraco.Web/Editors/AuthenticationController.cs
@@ -27,6 +27,7 @@ using IUser = Umbraco.Core.Models.Membership.IUser;
 using Umbraco.Core.Mapping;
 using Umbraco.Web.Models.Identity;
 using Umbraco.Core.Configuration.UmbracoSettings;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.IO;
 using Umbraco.Web.Routing;
 
@@ -44,13 +45,14 @@ namespace Umbraco.Web.Editors
         private BackOfficeUserManager<BackOfficeIdentityUser> _userManager;
         private BackOfficeSignInManager _signInManager;
         private readonly IUserPasswordConfiguration _passwordConfiguration;
+        private readonly IHostingEnvironment _hostingEnvironment;
         private readonly IRuntimeState _runtimeState;
         private readonly ISecuritySettings _securitySettings;
-        private readonly IIOHelper _ioHelper;
 
         public AuthenticationController(
             IUserPasswordConfiguration passwordConfiguration,
             IGlobalSettings globalSettings,
+            IHostingEnvironment hostingEnvironment,
             IUmbracoContextAccessor umbracoContextAccessor,
             ISqlContext sqlContext,
             ServiceContext services,
@@ -59,14 +61,13 @@ namespace Umbraco.Web.Editors
             IRuntimeState runtimeState,
             UmbracoMapper umbracoMapper,
             ISecuritySettings securitySettings,
-            IIOHelper ioHelper,
             IPublishedUrlProvider publishedUrlProvider)
             : base(globalSettings, umbracoContextAccessor, sqlContext, services, appCaches, logger, runtimeState, umbracoMapper, publishedUrlProvider)
         {
             _passwordConfiguration = passwordConfiguration ?? throw new ArgumentNullException(nameof(passwordConfiguration));
+            _hostingEnvironment = hostingEnvironment ?? throw new ArgumentNullException(nameof(hostingEnvironment));
             _runtimeState = runtimeState ?? throw new ArgumentNullException(nameof(runtimeState));
             _securitySettings = securitySettings ?? throw new ArgumentNullException(nameof(securitySettings));
-            _ioHelper = ioHelper ?? throw new ArgumentNullException(nameof(ioHelper));
         }
 
         protected BackOfficeUserManager<BackOfficeIdentityUser> UserManager => _userManager
@@ -534,7 +535,7 @@ namespace Umbraco.Web.Editors
             var action = urlHelper.Action("ValidatePasswordResetCode", "BackOffice",
                 new
                 {
-                    area = _ioHelper.GetUmbracoMvcArea(),
+                    area = GlobalSettings.GetUmbracoMvcArea(_hostingEnvironment),
                     u = userId,
                     r = code
                 });
diff --git a/src/Umbraco.Web/Editors/BackOfficeController.cs b/src/Umbraco.Web/Editors/BackOfficeController.cs
index 22c744621a..587e6c5ea3 100644
--- a/src/Umbraco.Web/Editors/BackOfficeController.cs
+++ b/src/Umbraco.Web/Editors/BackOfficeController.cs
@@ -44,7 +44,6 @@ namespace Umbraco.Web.Editors
     [DisableBrowserCache]
     public class BackOfficeController : UmbracoController
     {
-        private readonly IManifestParser _manifestParser;
         private readonly UmbracoFeatures _features;
         private readonly IRuntimeState _runtimeState;
         private BackOfficeUserManager<BackOfficeIdentityUser> _userManager;
@@ -52,7 +51,6 @@ namespace Umbraco.Web.Editors
         private readonly IUmbracoVersion _umbracoVersion;
         private readonly IGridConfig _gridConfig;
         private readonly IContentSettings _contentSettings;
-        private readonly IIOHelper _ioHelper;
         private readonly TreeCollection _treeCollection;
         private readonly IHostingEnvironment _hostingEnvironment;
         private readonly IHttpContextAccessor _httpContextAccessor;
@@ -61,7 +59,6 @@ namespace Umbraco.Web.Editors
         private readonly IRuntimeMinifier _runtimeMinifier;
 
         public BackOfficeController(
-            IManifestParser manifestParser,
             UmbracoFeatures features,
             IGlobalSettings globalSettings,
             IUmbracoContextAccessor umbracoContextAccessor,
@@ -72,7 +69,6 @@ namespace Umbraco.Web.Editors
             IUmbracoVersion umbracoVersion,
             IGridConfig gridConfig,
             IContentSettings contentSettings,
-            IIOHelper ioHelper,
             TreeCollection treeCollection,
             IHostingEnvironment hostingEnvironment,
             IHttpContextAccessor httpContextAccessor,
@@ -82,13 +78,11 @@ namespace Umbraco.Web.Editors
             : base(globalSettings, umbracoContextAccessor, services, appCaches, profilingLogger)
 
         {
-            _manifestParser = manifestParser;
             _features = features;
             _runtimeState = runtimeState;
             _umbracoVersion = umbracoVersion;
             _gridConfig = gridConfig ?? throw new ArgumentNullException(nameof(gridConfig));
             _contentSettings = contentSettings ?? throw new ArgumentNullException(nameof(contentSettings));
-            _ioHelper = ioHelper ?? throw new ArgumentNullException(nameof(ioHelper));
             _treeCollection = treeCollection ?? throw new ArgumentNullException(nameof(treeCollection));
             _hostingEnvironment = hostingEnvironment;
             _httpContextAccessor = httpContextAccessor;
@@ -111,9 +105,9 @@ namespace Umbraco.Web.Editors
         {
             return await RenderDefaultOrProcessExternalLoginAsync(
                 () =>
-                    View(_ioHelper.BackOfficePath.EnsureEndsWith('/') + "Views/Default.cshtml", new BackOfficeModel(_features, GlobalSettings, _umbracoVersion, _contentSettings,_ioHelper, _treeCollection, _httpContextAccessor, _hostingEnvironment, _runtimeSettings, _securitySettings)),
+                    View(GlobalSettings.GetBackOfficePath(_hostingEnvironment).EnsureEndsWith('/') + "Views/Default.cshtml", new BackOfficeModel(_features, GlobalSettings, _umbracoVersion, _contentSettings, _treeCollection, _httpContextAccessor, _hostingEnvironment, _runtimeSettings, _securitySettings)),
                 () =>
-                    View(_ioHelper.BackOfficePath.EnsureEndsWith('/') + "Views/Default.cshtml", new BackOfficeModel(_features, GlobalSettings, _umbracoVersion, _contentSettings, _ioHelper, _treeCollection, _httpContextAccessor, _hostingEnvironment, _runtimeSettings, _securitySettings))
+                    View(GlobalSettings.GetBackOfficePath(_hostingEnvironment).EnsureEndsWith('/') + "Views/Default.cshtml", new BackOfficeModel(_features, GlobalSettings, _umbracoVersion, _contentSettings, _treeCollection, _httpContextAccessor, _hostingEnvironment, _runtimeSettings, _securitySettings))
                     );
         }
 
@@ -197,7 +191,7 @@ namespace Umbraco.Web.Editors
         {
             return await RenderDefaultOrProcessExternalLoginAsync(
                 //The default view to render when there is no external login info or errors
-                () => View(_ioHelper.BackOfficePath.EnsureEndsWith('/') + "Views/AuthorizeUpgrade.cshtml", new BackOfficeModel(_features, GlobalSettings, _umbracoVersion, _contentSettings, _ioHelper, _treeCollection, _httpContextAccessor, _hostingEnvironment, _runtimeSettings, _securitySettings)),
+                () => View(GlobalSettings.GetBackOfficePath(_hostingEnvironment).EnsureEndsWith('/') + "Views/AuthorizeUpgrade.cshtml", new BackOfficeModel(_features, GlobalSettings, _umbracoVersion, _contentSettings, _treeCollection, _httpContextAccessor, _hostingEnvironment, _runtimeSettings, _securitySettings)),
                 //The ActionResult to perform if external login is successful
                 () => Redirect("/"));
         }
@@ -248,7 +242,7 @@ namespace Umbraco.Web.Editors
         [OutputCache(Order = 1, VaryByParam = "none", Location = OutputCacheLocation.Server, Duration = 5000)]
         public async Task<JavaScriptResult> Application()
         {
-            var result = await _runtimeMinifier.GetScriptForLoadingBackOfficeAsync(GlobalSettings, _ioHelper);
+            var result = await _runtimeMinifier.GetScriptForLoadingBackOfficeAsync(GlobalSettings, _hostingEnvironment);
 
             return JavaScript(result);
         }
@@ -270,7 +264,7 @@ namespace Umbraco.Web.Editors
         [MinifyJavaScriptResult(Order = 1)]
         public JavaScriptResult ServerVariables()
         {
-            var serverVars = new BackOfficeServerVariables(Url, _runtimeState, _features, GlobalSettings, _umbracoVersion, _contentSettings, _ioHelper, _treeCollection, _httpContextAccessor, _hostingEnvironment, _runtimeSettings, _securitySettings, _runtimeMinifier);
+            var serverVars = new BackOfficeServerVariables(Url, _runtimeState, _features, GlobalSettings, _umbracoVersion, _contentSettings, _treeCollection, _httpContextAccessor, _hostingEnvironment, _runtimeSettings, _securitySettings, _runtimeMinifier);
 
             //cache the result if debugging is disabled
             var result = _hostingEnvironment.IsDebugMode
@@ -364,7 +358,7 @@ namespace Umbraco.Web.Editors
             if (defaultResponse == null) throw new ArgumentNullException("defaultResponse");
             if (externalSignInResponse == null) throw new ArgumentNullException("externalSignInResponse");
 
-            ViewData.SetUmbracoPath(_ioHelper.GetUmbracoMvcArea());
+            ViewData.SetUmbracoPath(GlobalSettings.GetUmbracoMvcArea(_hostingEnvironment));
 
             //check if there is the TempData with the any token name specified, if so, assign to view bag and render the view
             if (ViewData.FromTempData(TempData, ViewDataExtensions.TokenExternalSignInError) ||
diff --git a/src/Umbraco.Web/Editors/BackOfficeModel.cs b/src/Umbraco.Web/Editors/BackOfficeModel.cs
index 3aefd58e8f..cf1b4a3879 100644
--- a/src/Umbraco.Web/Editors/BackOfficeModel.cs
+++ b/src/Umbraco.Web/Editors/BackOfficeModel.cs
@@ -11,7 +11,7 @@ namespace Umbraco.Web.Editors
     public class BackOfficeModel
     {
         public BackOfficeModel(UmbracoFeatures features, IGlobalSettings globalSettings, IUmbracoVersion umbracoVersion,
-            IContentSettings contentSettings, IIOHelper ioHelper, TreeCollection treeCollection,
+            IContentSettings contentSettings, TreeCollection treeCollection,
             IHttpContextAccessor httpContextAccessor, IHostingEnvironment hostingEnvironment,
             IRuntimeSettings runtimeSettings, ISecuritySettings securitySettings)
         {
@@ -19,23 +19,24 @@ namespace Umbraco.Web.Editors
             GlobalSettings = globalSettings;
             UmbracoVersion = umbracoVersion;
             ContentSettings = contentSettings;
-            IOHelper = ioHelper;
             TreeCollection = treeCollection;
             HttpContextAccessor = httpContextAccessor;
             HostingEnvironment = hostingEnvironment;
             RuntimeSettings = runtimeSettings;
             SecuritySettings = securitySettings;
+            BackOfficePath = GlobalSettings.GetBackOfficePath(HostingEnvironment);
         }
 
         public UmbracoFeatures Features { get; }
         public IGlobalSettings GlobalSettings { get; }
         public IUmbracoVersion UmbracoVersion { get; }
         public IContentSettings ContentSettings { get; }
-        public IIOHelper IOHelper { get; }
         public TreeCollection TreeCollection { get; }
         public IHttpContextAccessor HttpContextAccessor { get; }
         public IHostingEnvironment HostingEnvironment { get; }
         public IRuntimeSettings RuntimeSettings { get; set; }
         public ISecuritySettings SecuritySettings { get; set; }
+
+        public string BackOfficePath { get; } 
     }
 }
diff --git a/src/Umbraco.Web/Editors/BackOfficePreviewModel.cs b/src/Umbraco.Web/Editors/BackOfficePreviewModel.cs
index 394a0366af..2235d8fdaf 100644
--- a/src/Umbraco.Web/Editors/BackOfficePreviewModel.cs
+++ b/src/Umbraco.Web/Editors/BackOfficePreviewModel.cs
@@ -14,8 +14,8 @@ namespace Umbraco.Web.Editors
         private readonly UmbracoFeatures _features;
         public IEnumerable<ILanguage> Languages { get; }
 
-        public BackOfficePreviewModel(UmbracoFeatures features, IGlobalSettings globalSettings, IUmbracoVersion umbracoVersion, IEnumerable<ILanguage> languages, IContentSettings contentSettings, IIOHelper ioHelper, TreeCollection treeCollection, IHttpContextAccessor httpContextAccessor, IHostingEnvironment hostingEnvironment, IRuntimeSettings runtimeSettings, ISecuritySettings securitySettings)
-            : base(features, globalSettings, umbracoVersion, contentSettings, ioHelper, treeCollection, httpContextAccessor, hostingEnvironment, runtimeSettings, securitySettings)
+        public BackOfficePreviewModel(UmbracoFeatures features, IGlobalSettings globalSettings, IUmbracoVersion umbracoVersion, IEnumerable<ILanguage> languages, IContentSettings contentSettings, TreeCollection treeCollection, IHttpContextAccessor httpContextAccessor, IHostingEnvironment hostingEnvironment, IRuntimeSettings runtimeSettings, ISecuritySettings securitySettings)
+            : base(features, globalSettings, umbracoVersion, contentSettings, treeCollection, httpContextAccessor, hostingEnvironment, runtimeSettings, securitySettings)
         {
             _features = features;
             Languages = languages;
diff --git a/src/Umbraco.Web/Editors/BackOfficeServerVariables.cs b/src/Umbraco.Web/Editors/BackOfficeServerVariables.cs
index 6db8650f19..058f787324 100644
--- a/src/Umbraco.Web/Editors/BackOfficeServerVariables.cs
+++ b/src/Umbraco.Web/Editors/BackOfficeServerVariables.cs
@@ -35,7 +35,6 @@ namespace Umbraco.Web.Editors
         private readonly IGlobalSettings _globalSettings;
         private readonly IUmbracoVersion _umbracoVersion;
         private readonly IContentSettings _contentSettings;
-        private readonly IIOHelper _ioHelper;
         private readonly TreeCollection _treeCollection;
         private readonly IHttpContextAccessor _httpContextAccessor;
         private readonly IHostingEnvironment _hostingEnvironment;
@@ -50,7 +49,6 @@ namespace Umbraco.Web.Editors
             IGlobalSettings globalSettings,
             IUmbracoVersion umbracoVersion,
             IContentSettings contentSettings,
-            IIOHelper ioHelper,
             TreeCollection treeCollection,
             IHttpContextAccessor httpContextAccessor,
             IHostingEnvironment hostingEnvironment,
@@ -64,7 +62,6 @@ namespace Umbraco.Web.Editors
             _globalSettings = globalSettings;
             _umbracoVersion = umbracoVersion;
             _contentSettings = contentSettings ?? throw new ArgumentNullException(nameof(contentSettings));
-            _ioHelper = ioHelper ?? throw new ArgumentNullException(nameof(ioHelper));
             _treeCollection = treeCollection ?? throw new ArgumentNullException(nameof(treeCollection));
             _httpContextAccessor = httpContextAccessor;
             _hostingEnvironment = hostingEnvironment;
@@ -347,9 +344,9 @@ namespace Umbraco.Web.Editors
                 {
                     "umbracoSettings", new Dictionary<string, object>
                     {
-                        {"umbracoPath", _ioHelper.BackOfficePath},
-                        {"mediaPath", _ioHelper.ResolveUrl(globalSettings.UmbracoMediaPath).TrimEnd('/')},
-                        {"appPluginsPath", _ioHelper.ResolveUrl(Constants.SystemDirectories.AppPlugins).TrimEnd('/')},
+                        {"umbracoPath", _globalSettings.GetBackOfficePath(_hostingEnvironment)},
+                        {"mediaPath", _hostingEnvironment.ToAbsolute(globalSettings.UmbracoMediaPath).TrimEnd('/')},
+                        {"appPluginsPath", _hostingEnvironment.ToAbsolute(Constants.SystemDirectories.AppPlugins).TrimEnd('/')},
                         {
                             "imageFileTypes",
                             string.Join(",", _contentSettings.ImageFileTypes)
@@ -368,7 +365,7 @@ namespace Umbraco.Web.Editors
                         },
                         {"keepUserLoggedIn", _securitySettings.KeepUserLoggedIn},
                         {"usernameIsEmail", _securitySettings.UsernameIsEmail},
-                        {"cssPath", _ioHelper.ResolveUrl(globalSettings.UmbracoCssPath).TrimEnd('/')},
+                        {"cssPath", _hostingEnvironment.ToAbsolute(globalSettings.UmbracoCssPath).TrimEnd('/')},
                         {"allowPasswordReset", _securitySettings.AllowPasswordReset},
                         {"loginBackgroundImage", _contentSettings.LoginBackgroundImage},
                         {"showUserInvite", EmailSender.CanSendRequiredEmail(globalSettings)},
diff --git a/src/Umbraco.Web/Editors/CurrentUserController.cs b/src/Umbraco.Web/Editors/CurrentUserController.cs
index 0b288735fe..5715d0ca7c 100644
--- a/src/Umbraco.Web/Editors/CurrentUserController.cs
+++ b/src/Umbraco.Web/Editors/CurrentUserController.cs
@@ -22,6 +22,7 @@ using Umbraco.Web.Security;
 using Umbraco.Web.WebApi.Filters;
 using Umbraco.Core.Mapping;
 using Umbraco.Core.Configuration.UmbracoSettings;
+using Umbraco.Core.Hosting;
 using Umbraco.Web.Routing;
 using Umbraco.Core.Media;
 
@@ -35,7 +36,7 @@ namespace Umbraco.Web.Editors
     {
         private readonly IMediaFileSystem _mediaFileSystem;
         private readonly IContentSettings _contentSettings;
-        private readonly IIOHelper _ioHelper;
+        private readonly IHostingEnvironment _hostingEnvironment;
         private readonly IImageUrlGenerator _imageUrlGenerator;
 
         public CurrentUserController(
@@ -50,14 +51,14 @@ namespace Umbraco.Web.Editors
             IShortStringHelper shortStringHelper,
             UmbracoMapper umbracoMapper,
             IContentSettings contentSettings,
-            IIOHelper ioHelper,
+            IHostingEnvironment hostingEnvironment,
             IImageUrlGenerator imageUrlGenerator,
             IPublishedUrlProvider publishedUrlProvider)
             : base(globalSettings, umbracoContextAccessor, sqlContext, services, appCaches, logger, runtimeState, shortStringHelper, umbracoMapper, publishedUrlProvider)
         {
             _mediaFileSystem = mediaFileSystem;
             _contentSettings = contentSettings ?? throw new ArgumentNullException(nameof(contentSettings));
-            _ioHelper = ioHelper ?? throw new ArgumentNullException(nameof(ioHelper));
+            _hostingEnvironment = hostingEnvironment ?? throw new ArgumentNullException(nameof(hostingEnvironment));
             _imageUrlGenerator = imageUrlGenerator;
         }
 
@@ -192,7 +193,7 @@ namespace Umbraco.Web.Editors
         public async Task<HttpResponseMessage> PostSetAvatar()
         {
             //borrow the logic from the user controller
-            return await UsersController.PostSetAvatarInternal(Request, Services.UserService, AppCaches.RuntimeCache,  _mediaFileSystem, ShortStringHelper, _contentSettings, _ioHelper, _imageUrlGenerator, Security.GetUserId().ResultOr(0));
+            return await UsersController.PostSetAvatarInternal(Request, Services.UserService, AppCaches.RuntimeCache,  _mediaFileSystem, ShortStringHelper, _contentSettings, _hostingEnvironment, _imageUrlGenerator, Security.GetUserId().ResultOr(0));
         }
 
         /// <summary>
diff --git a/src/Umbraco.Web/Editors/PreviewController.cs b/src/Umbraco.Web/Editors/PreviewController.cs
index db14be84ec..45aa8a4295 100644
--- a/src/Umbraco.Web/Editors/PreviewController.cs
+++ b/src/Umbraco.Web/Editors/PreviewController.cs
@@ -32,7 +32,6 @@ namespace Umbraco.Web.Editors
         private readonly ILocalizationService _localizationService;
         private readonly IUmbracoVersion _umbracoVersion;
         private readonly IContentSettings _contentSettings;
-        private readonly IIOHelper _ioHelper;
         private readonly TreeCollection _treeCollection;
         private readonly IHttpContextAccessor _httpContextAccessor;
         private readonly IHostingEnvironment _hostingEnvironment;
@@ -49,7 +48,6 @@ namespace Umbraco.Web.Editors
             ILocalizationService localizationService,
             IUmbracoVersion umbracoVersion,
             IContentSettings contentSettings,
-            IIOHelper ioHelper,
             TreeCollection treeCollection,
             IHttpContextAccessor httpContextAccessor,
             IHostingEnvironment hostingEnvironment,
@@ -65,7 +63,6 @@ namespace Umbraco.Web.Editors
             _localizationService = localizationService;
             _umbracoVersion = umbracoVersion;
             _contentSettings = contentSettings ?? throw new ArgumentNullException(nameof(contentSettings));
-            _ioHelper = ioHelper ?? throw new ArgumentNullException(nameof(ioHelper));
             _treeCollection = treeCollection;
             _httpContextAccessor = httpContextAccessor;
             _hostingEnvironment = hostingEnvironment;
@@ -81,7 +78,7 @@ namespace Umbraco.Web.Editors
         {
             var availableLanguages = _localizationService.GetAllLanguages();
 
-            var model = new BackOfficePreviewModel(_features, _globalSettings, _umbracoVersion, availableLanguages, _contentSettings, _ioHelper, _treeCollection, _httpContextAccessor, _hostingEnvironment, _runtimeSettings, _securitySettings);
+            var model = new BackOfficePreviewModel(_features, _globalSettings, _umbracoVersion, availableLanguages, _contentSettings, _treeCollection, _httpContextAccessor, _hostingEnvironment, _runtimeSettings, _securitySettings);
 
             if (model.PreviewExtendedHeaderView.IsNullOrWhiteSpace() == false)
             {
@@ -92,7 +89,7 @@ namespace Umbraco.Web.Editors
                 }
             }
 
-            return View(_ioHelper.BackOfficePath.EnsureEndsWith('/') + "Views/Preview/" + "Index.cshtml", model);
+            return View(_globalSettings.GetBackOfficePath(_hostingEnvironment).EnsureEndsWith('/') + "Views/Preview/" + "Index.cshtml", model);
         }
 
         /// <summary>
@@ -104,7 +101,7 @@ namespace Umbraco.Web.Editors
         public async Task<JavaScriptResult> Application()
         {
             var files = await _runtimeMinifier.GetAssetPathsAsync(BackOfficeWebAssets.UmbracoPreviewJsBundleName);
-            var result = BackOfficeJavaScriptInitializer.GetJavascriptInitialization(files, "umbraco.preview", _globalSettings, _ioHelper);
+            var result = BackOfficeJavaScriptInitializer.GetJavascriptInitialization(files, "umbraco.preview", _globalSettings, _hostingEnvironment);
 
             return JavaScript(result);
         }
diff --git a/src/Umbraco.Web/Editors/UsersController.cs b/src/Umbraco.Web/Editors/UsersController.cs
index eec10be1ac..843b7cc583 100644
--- a/src/Umbraco.Web/Editors/UsersController.cs
+++ b/src/Umbraco.Web/Editors/UsersController.cs
@@ -35,6 +35,7 @@ using IUser = Umbraco.Core.Models.Membership.IUser;
 using Task = System.Threading.Tasks.Task;
 using Umbraco.Core.Mapping;
 using Umbraco.Core.Configuration.UmbracoSettings;
+using Umbraco.Core.Hosting;
 using Umbraco.Web.Routing;
 using Umbraco.Core.Media;
 
@@ -48,7 +49,7 @@ namespace Umbraco.Web.Editors
     {
         private readonly IMediaFileSystem _mediaFileSystem;
         private readonly IContentSettings _contentSettings;
-        private readonly IIOHelper _ioHelper;
+        private readonly IHostingEnvironment _hostingEnvironment;
         private readonly ISqlContext _sqlContext;
         private readonly IImageUrlGenerator _imageUrlGenerator;
         private readonly ISecuritySettings _securitySettings;
@@ -65,7 +66,7 @@ namespace Umbraco.Web.Editors
             IShortStringHelper shortStringHelper,
             UmbracoMapper umbracoMapper,
             IContentSettings contentSettings,
-            IIOHelper ioHelper,
+            IHostingEnvironment hostingEnvironment,
             IImageUrlGenerator imageUrlGenerator,
             IPublishedUrlProvider publishedUrlProvider,
             ISecuritySettings securitySettings)
@@ -73,7 +74,7 @@ namespace Umbraco.Web.Editors
         {
             _mediaFileSystem = mediaFileSystem;
             _contentSettings = contentSettings ?? throw new ArgumentNullException(nameof(contentSettings));
-            _ioHelper = ioHelper;
+            _hostingEnvironment = hostingEnvironment;
             _sqlContext = sqlContext;
             _imageUrlGenerator = imageUrlGenerator;
             _securitySettings = securitySettings;
@@ -97,17 +98,17 @@ namespace Umbraco.Web.Editors
         [AdminUsersAuthorize]
         public async Task<HttpResponseMessage> PostSetAvatar(int id)
         {
-            return await PostSetAvatarInternal(Request, Services.UserService, AppCaches.RuntimeCache, _mediaFileSystem, ShortStringHelper, _contentSettings, _ioHelper, _imageUrlGenerator, id);
+            return await PostSetAvatarInternal(Request, Services.UserService, AppCaches.RuntimeCache, _mediaFileSystem, ShortStringHelper, _contentSettings, _hostingEnvironment, _imageUrlGenerator, id);
         }
 
-        internal static async Task<HttpResponseMessage> PostSetAvatarInternal(HttpRequestMessage request, IUserService userService, IAppCache cache, IMediaFileSystem mediaFileSystem, IShortStringHelper shortStringHelper, IContentSettings contentSettings, IIOHelper ioHelper, IImageUrlGenerator imageUrlGenerator, int id)
+        internal static async Task<HttpResponseMessage> PostSetAvatarInternal(HttpRequestMessage request, IUserService userService, IAppCache cache, IMediaFileSystem mediaFileSystem, IShortStringHelper shortStringHelper, IContentSettings contentSettings, IHostingEnvironment hostingEnvironment, IImageUrlGenerator imageUrlGenerator, int id)
         {
             if (request.Content.IsMimeMultipartContent() == false)
             {
                 throw new HttpResponseException(HttpStatusCode.UnsupportedMediaType);
             }
 
-            var root = ioHelper.MapPath(Constants.SystemDirectories.TempFileUploads);
+            var root = hostingEnvironment.MapPath(Constants.SystemDirectories.TempFileUploads);
             //ensure it exists
             Directory.CreateDirectory(root);
             var provider = new MultipartFormDataStreamProvider(root);
@@ -488,7 +489,7 @@ namespace Umbraco.Web.Editors
             var action = urlHelper.Action("VerifyInvite", "BackOffice",
                 new
                 {
-                    area = _ioHelper.GetUmbracoMvcArea(),
+                    area = GlobalSettings.GetUmbracoMvcArea(_hostingEnvironment),
                     invite = inviteToken
                 });
 
diff --git a/src/Umbraco.Web/HtmlHelperBackOfficeExtensions.cs b/src/Umbraco.Web/HtmlHelperBackOfficeExtensions.cs
index c20b82a6de..eefb02ef6d 100644
--- a/src/Umbraco.Web/HtmlHelperBackOfficeExtensions.cs
+++ b/src/Umbraco.Web/HtmlHelperBackOfficeExtensions.cs
@@ -30,20 +30,24 @@ namespace Umbraco.Web
         /// </summary>
         /// <param name="html"></param>
         /// <param name="uri"></param>
-        /// <param name="externalLoginsUrl">
-        /// The post url used to sign in with external logins - this can change depending on for what service the external login is service.
-        /// Example: normal back office login or authenticating upgrade login
-        /// </param>
         /// <param name="features"></param>
         /// <param name="globalSettings"></param>
+        /// <param name="umbracoVersion"></param>
+        /// <param name="contentSettings"></param>
+        /// <param name="treeCollection"></param>
+        /// <param name="httpContextAccessor"></param>
+        /// <param name="hostingEnvironment"></param>
+        /// <param name="settings"></param>
+        /// <param name="securitySettings"></param>
+        /// <param name="runtimeMinifier"></param>
         /// <returns></returns>
         /// <remarks>
         /// These are the bare minimal server variables that are required for the application to start without being authenticated,
         /// we will load the rest of the server vars after the user is authenticated.
         /// </remarks>
-        public static IHtmlString BareMinimumServerVariablesScript(this HtmlHelper html, UrlHelper uri, string externalLoginsUrl, UmbracoFeatures features, IGlobalSettings globalSettings, IUmbracoVersion umbracoVersion, IContentSettings contentSettings, IIOHelper ioHelper, TreeCollection treeCollection, IHttpContextAccessor httpContextAccessor, IHostingEnvironment hostingEnvironment, IRuntimeSettings settings, ISecuritySettings securitySettings, IRuntimeMinifier runtimeMinifier)
+        public static IHtmlString BareMinimumServerVariablesScript(this HtmlHelper html, UrlHelper uri, UmbracoFeatures features, IGlobalSettings globalSettings, IUmbracoVersion umbracoVersion, IContentSettings contentSettings, TreeCollection treeCollection, IHttpContextAccessor httpContextAccessor, IHostingEnvironment hostingEnvironment, IRuntimeSettings settings, ISecuritySettings securitySettings, IRuntimeMinifier runtimeMinifier)
         {
-            var serverVars = new BackOfficeServerVariables(uri, Current.RuntimeState, features, globalSettings, umbracoVersion, contentSettings, ioHelper, treeCollection, httpContextAccessor, hostingEnvironment, settings, securitySettings, runtimeMinifier);
+            var serverVars = new BackOfficeServerVariables(uri, Current.RuntimeState, features, globalSettings, umbracoVersion, contentSettings, treeCollection, httpContextAccessor, hostingEnvironment, settings, securitySettings, runtimeMinifier);
             var minVars = serverVars.BareMinimumServerVariables();
 
             var str = @"<script type=""text/javascript"">
diff --git a/src/Umbraco.Web/Install/Controllers/InstallController.cs b/src/Umbraco.Web/Install/Controllers/InstallController.cs
index 02824489ee..b59692db79 100644
--- a/src/Umbraco.Web/Install/Controllers/InstallController.cs
+++ b/src/Umbraco.Web/Install/Controllers/InstallController.cs
@@ -1,6 +1,7 @@
 using System.Web.Mvc;
 using Umbraco.Core;
 using Umbraco.Core.Configuration;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.IO;
 using Umbraco.Core.Logging;
 using Umbraco.Core.WebAssets;
@@ -21,30 +22,24 @@ namespace Umbraco.Web.Install.Controllers
         private readonly IUmbracoContextAccessor _umbracoContextAccessor;
         private readonly InstallHelper _installHelper;
         private readonly IRuntimeState _runtime;
-        private readonly ILogger _logger;
         private readonly IGlobalSettings _globalSettings;
-        private readonly IUmbracoVersion _umbracoVersion;
-        private readonly IIOHelper _ioHelper;
+        private readonly IHostingEnvironment _hostingEnvironment;
         private readonly IRuntimeMinifier _runtimeMinifier;
 
         public InstallController(
             IUmbracoContextAccessor umbracoContextAccessor,
             InstallHelper installHelper,
             IRuntimeState runtime,
-            ILogger logger,
             IGlobalSettings globalSettings,
-            IUmbracoVersion umbracoVersion,
-            IIOHelper ioHelper,
-            IRuntimeMinifier runtimeMinifier)
+            IRuntimeMinifier runtimeMinifier,
+            IHostingEnvironment hostingEnvironment)
         {
             _umbracoContextAccessor = umbracoContextAccessor;
             _installHelper = installHelper;
             _runtime = runtime;
-            _logger = logger;
             _globalSettings = globalSettings;
-            _umbracoVersion = umbracoVersion;
-            _ioHelper = ioHelper;
             _runtimeMinifier = runtimeMinifier;
+            _hostingEnvironment = hostingEnvironment;
         }
 
         [HttpGet]
@@ -73,12 +68,12 @@ namespace Umbraco.Web.Install.Controllers
             ViewData.SetInstallApiBaseUrl(Url.GetUmbracoApiService("GetSetup", "InstallApi", "UmbracoInstall").TrimEnd("GetSetup"));
 
             // get the base umbraco folder
-            ViewData.SetUmbracoBaseFolder(_ioHelper.ResolveUrl(_globalSettings.UmbracoPath));
+            ViewData.SetUmbracoBaseFolder(_hostingEnvironment.ToAbsolute(_globalSettings.UmbracoPath));
 
             _installHelper.InstallStatus(false, "");
 
             // always ensure full path (see NOTE in the class remarks)
-            return View(_ioHelper.BackOfficePath.EnsureEndsWith('/') + "install/views/index.cshtml");
+            return View(_globalSettings.GetBackOfficePath(_hostingEnvironment).EnsureEndsWith('/') + "install/views/index.cshtml");
         }
     }
 }
diff --git a/src/Umbraco.Web/Mvc/AreaRegistrationExtensions.cs b/src/Umbraco.Web/Mvc/AreaRegistrationExtensions.cs
index 22e5911cf8..118c53a7f0 100644
--- a/src/Umbraco.Web/Mvc/AreaRegistrationExtensions.cs
+++ b/src/Umbraco.Web/Mvc/AreaRegistrationExtensions.cs
@@ -7,6 +7,7 @@ using System.Web.SessionState;
 using Umbraco.Core;
 using Umbraco.Core.Configuration;
 using Umbraco.Core.Exceptions;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.IO;
 using Umbraco.Web.Composing;
 using Umbraco.Web.WebApi;
@@ -19,7 +20,7 @@ namespace Umbraco.Web.Mvc
         /// Creates a custom individual route for the specified controller plugin. Individual routes
         /// are required by controller plugins to map to a unique URL based on ID.
         /// </summary>
-        /// <param name="ioHelper"></param>
+        /// <param name="hostingEnvironment"></param>
         /// <param name="controllerName"></param>
         /// <param name="controllerType"></param>
         /// <param name="routes">An existing route collection</param>
@@ -39,10 +40,11 @@ namespace Umbraco.Web.Mvc
         /// if not specified, will just route like:
         ///     /umbraco/areaname
         /// </param>
+        /// <param name="globalSettings"></param>
         /// <remarks>
         /// </remarks>
         internal static Route RouteControllerPlugin(this AreaRegistration area,
-            IIOHelper ioHelper,
+            IGlobalSettings globalSettings, IHostingEnvironment hostingEnvironment,
             string controllerName, Type controllerType, RouteCollection routes,
             string controllerSuffixName, string defaultAction, object defaultId,
             string umbracoTokenValue = "backoffice",
@@ -58,7 +60,7 @@ namespace Umbraco.Web.Mvc
             if (routes == null) throw new ArgumentNullException(nameof(routes));
             if (defaultId == null) throw new ArgumentNullException(nameof(defaultId));
 
-            var umbracoArea = ioHelper.GetUmbracoMvcArea();
+            var umbracoArea = globalSettings.GetUmbracoMvcArea(hostingEnvironment);
 
             //routes are explicitly named with controller names and IDs
             var url = umbracoArea + "/" +
diff --git a/src/Umbraco.Web/Mvc/BackOfficeArea.cs b/src/Umbraco.Web/Mvc/BackOfficeArea.cs
index 82c0bbf909..37b9f7e44b 100644
--- a/src/Umbraco.Web/Mvc/BackOfficeArea.cs
+++ b/src/Umbraco.Web/Mvc/BackOfficeArea.cs
@@ -1,6 +1,7 @@
 using System.Web.Mvc;
 using Umbraco.Web.Composing;
 using Umbraco.Core.Configuration;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.IO;
 using Umbraco.Web.Editors;
 
@@ -11,11 +12,13 @@ namespace Umbraco.Web.Mvc
     /// </summary>
     internal class BackOfficeArea : AreaRegistration
     {
-        private readonly IIOHelper _ioHelper;
+        private readonly IGlobalSettings _globalSettings;
+        private readonly IHostingEnvironment _hostingEnvironment;
 
-        public BackOfficeArea(IIOHelper ioHelper)
+        public BackOfficeArea(IGlobalSettings globalSettings, IHostingEnvironment hostingEnvironment)
         {
-            _ioHelper = ioHelper;
+            _globalSettings = globalSettings;
+            _hostingEnvironment = hostingEnvironment;
         }
 
         /// <summary>
@@ -49,6 +52,6 @@ namespace Umbraco.Web.Mvc
                 new[] {typeof (BackOfficeController).Namespace});
         }
 
-        public override string AreaName => _ioHelper.GetUmbracoMvcArea();
+        public override string AreaName => _globalSettings.GetUmbracoMvcArea(_hostingEnvironment);
     }
 }
diff --git a/src/Umbraco.Web/Mvc/PluginControllerArea.cs b/src/Umbraco.Web/Mvc/PluginControllerArea.cs
index fddf04b391..838e304847 100644
--- a/src/Umbraco.Web/Mvc/PluginControllerArea.cs
+++ b/src/Umbraco.Web/Mvc/PluginControllerArea.cs
@@ -6,6 +6,7 @@ using System.Web.Routing;
 using Umbraco.Core;
 using Umbraco.Core.Configuration;
 using Umbraco.Core.Composing;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.IO;
 using Umbraco.Web.WebApi;
 
@@ -17,7 +18,7 @@ namespace Umbraco.Web.Mvc
     internal class PluginControllerArea : AreaRegistration
     {
         private readonly IGlobalSettings _globalSettings;
-        private readonly IIOHelper _ioHelper;
+        private readonly IHostingEnvironment _hostingEnvironment;
         private readonly IEnumerable<PluginControllerMetadata> _surfaceControllers;
         private readonly IEnumerable<PluginControllerMetadata> _apiControllers;
         private readonly string _areaName;
@@ -27,11 +28,12 @@ namespace Umbraco.Web.Mvc
         /// based on their PluginControllerAttribute. If they are not the same an exception will be thrown.
         /// </summary>
         /// <param name="globalSettings"></param>
+        /// <param name="hostingEnvironment"></param>
         /// <param name="pluginControllers"></param>
-        public PluginControllerArea(IGlobalSettings globalSettings, IIOHelper ioHelper, IEnumerable<PluginControllerMetadata> pluginControllers)
+        public PluginControllerArea(IGlobalSettings globalSettings, IHostingEnvironment hostingEnvironment, IEnumerable<PluginControllerMetadata> pluginControllers)
         {
             _globalSettings = globalSettings;
-            _ioHelper = ioHelper;
+            _hostingEnvironment = hostingEnvironment;
             var controllers = pluginControllers.ToArray();
 
             if (controllers.Any(x => x.AreaName.IsNullOrWhiteSpace()))
@@ -77,7 +79,7 @@ namespace Umbraco.Web.Mvc
         {
             foreach (var s in surfaceControllers)
             {
-                var route = this.RouteControllerPlugin(_ioHelper,  s.ControllerName, s.ControllerType, routes, "", "Index", UrlParameter.Optional, "surface");
+                var route = this.RouteControllerPlugin(_globalSettings, _hostingEnvironment,  s.ControllerName, s.ControllerType, routes, "", "Index", UrlParameter.Optional, "surface");
                 //set the route handler to our SurfaceRouteHandler
                 route.RouteHandler = new SurfaceRouteHandler();
             }
@@ -92,7 +94,7 @@ namespace Umbraco.Web.Mvc
         {
             foreach (var s in apiControllers)
             {
-                this.RouteControllerPlugin(_ioHelper, s.ControllerName, s.ControllerType, routes, "", "", UrlParameter.Optional, "api",
+                this.RouteControllerPlugin(_globalSettings, _hostingEnvironment, s.ControllerName, s.ControllerType, routes, "", "", UrlParameter.Optional, "api",
                     isMvc: false,
                     areaPathPrefix: s.IsBackOffice ? "backoffice" : null);
             }
diff --git a/src/Umbraco.Web/Mvc/RenderViewEngine.cs b/src/Umbraco.Web/Mvc/RenderViewEngine.cs
index 2253bde03c..46ebf2f383 100644
--- a/src/Umbraco.Web/Mvc/RenderViewEngine.cs
+++ b/src/Umbraco.Web/Mvc/RenderViewEngine.cs
@@ -4,6 +4,7 @@ using System.IO;
 using System.Linq;
 using System.Web.Mvc;
 using Umbraco.Core.Composing;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.IO;
 using Umbraco.Web.Models;
 
@@ -15,7 +16,7 @@ namespace Umbraco.Web.Mvc
     /// </summary>
     public class RenderViewEngine : RazorViewEngine
     {
-        private readonly IIOHelper _ioHelper;
+        private readonly IHostingEnvironment _hostingEnvironment;
 
         private readonly IEnumerable<string> _supplementedViewLocations = new[] { "/{0}.cshtml" };
         //NOTE: we will make the main view location the last to be searched since if it is the first to be searched and there is both a view and a partial
@@ -26,9 +27,9 @@ namespace Umbraco.Web.Mvc
         /// <summary>
         /// Constructor
         /// </summary>
-        public RenderViewEngine(IIOHelper ioHelper)
+        public RenderViewEngine(IHostingEnvironment hostingEnvironment)
         {
-            _ioHelper = ioHelper ?? throw new ArgumentNullException(nameof(ioHelper));
+            _hostingEnvironment = hostingEnvironment ?? throw new ArgumentNullException(nameof(hostingEnvironment));
 
             const string templateFolder = Constants.ViewLocation;
 
@@ -47,7 +48,7 @@ namespace Umbraco.Web.Mvc
         /// </summary>
         private void EnsureFoldersAndFiles()
         {
-            var viewFolder = _ioHelper.MapPath(Constants.ViewLocation);
+            var viewFolder = _hostingEnvironment.MapPath(Constants.ViewLocation);
 
             // ensure the web.config file is in the ~/Views folder
             Directory.CreateDirectory(viewFolder);
diff --git a/src/Umbraco.Web/Mvc/UmbracoAuthorizeAttribute.cs b/src/Umbraco.Web/Mvc/UmbracoAuthorizeAttribute.cs
index 593289812f..cb594d1e7d 100644
--- a/src/Umbraco.Web/Mvc/UmbracoAuthorizeAttribute.cs
+++ b/src/Umbraco.Web/Mvc/UmbracoAuthorizeAttribute.cs
@@ -57,7 +57,7 @@ namespace Umbraco.Web.Mvc
         {
             if (redirectToUmbracoLogin)
             {
-                _redirectUrl = Current.IOHelper.BackOfficePath.EnsureStartsWith("~");
+                _redirectUrl = Current.Configs.Global().GetBackOfficePath(Current.HostingEnvironment).EnsureStartsWith("~");
             }
         }
 
diff --git a/src/Umbraco.Web/Runtime/WebInitialComponent.cs b/src/Umbraco.Web/Runtime/WebInitialComponent.cs
index 37d989edef..0243d2c887 100644
--- a/src/Umbraco.Web/Runtime/WebInitialComponent.cs
+++ b/src/Umbraco.Web/Runtime/WebInitialComponent.cs
@@ -8,6 +8,7 @@ using System.Web.Routing;
 using Umbraco.Core;
 using Umbraco.Core.Composing;
 using Umbraco.Core.Configuration;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.Strings;
 using Umbraco.Core.IO;
 using Umbraco.Web.Install;
@@ -25,7 +26,7 @@ namespace Umbraco.Web.Runtime
         private readonly SurfaceControllerTypeCollection _surfaceControllerTypes;
         private readonly UmbracoApiControllerTypeCollection _apiControllerTypes;
         private readonly IGlobalSettings _globalSettings;
-        private readonly IIOHelper _ioHelper;
+        private readonly IHostingEnvironment _hostingEnvironment;
         private readonly IShortStringHelper _shortStringHelper;
 
         public WebInitialComponent(
@@ -33,14 +34,14 @@ namespace Umbraco.Web.Runtime
             SurfaceControllerTypeCollection surfaceControllerTypes,
             UmbracoApiControllerTypeCollection apiControllerTypes,
             IGlobalSettings globalSettings,
-            IIOHelper ioHelper,
+            IHostingEnvironment hostingEnvironment,
             IShortStringHelper shortStringHelper)
         {
             _umbracoContextAccessor = umbracoContextAccessor;
             _surfaceControllerTypes = surfaceControllerTypes;
             _apiControllerTypes = apiControllerTypes;
             _globalSettings = globalSettings;
-            _ioHelper = ioHelper;
+            _hostingEnvironment = hostingEnvironment;
             _shortStringHelper = shortStringHelper;
         }
 
@@ -59,7 +60,7 @@ namespace Umbraco.Web.Runtime
             ConfigureGlobalFilters();
 
             // set routes
-            CreateRoutes(_umbracoContextAccessor, _globalSettings, _shortStringHelper, _surfaceControllerTypes, _apiControllerTypes, _ioHelper);
+            CreateRoutes(_umbracoContextAccessor, _globalSettings, _shortStringHelper, _surfaceControllerTypes, _apiControllerTypes, _hostingEnvironment);
         }
 
         public void Terminate()
@@ -94,7 +95,7 @@ namespace Umbraco.Web.Runtime
             ControllerBuilder.Current.SetControllerFactory(controllerFactory);
 
             // set the render & plugin view engines
-            ViewEngines.Engines.Add(new RenderViewEngine(_ioHelper));
+            ViewEngines.Engines.Add(new RenderViewEngine(_hostingEnvironment));
             ViewEngines.Engines.Add(new PluginViewEngine());
 
             //set model binder
@@ -114,9 +115,9 @@ namespace Umbraco.Web.Runtime
             IShortStringHelper shortStringHelper,
             SurfaceControllerTypeCollection surfaceControllerTypes,
             UmbracoApiControllerTypeCollection apiControllerTypes,
-            IIOHelper ioHelper)
+            IHostingEnvironment hostingEnvironment)
         {
-            var umbracoPath = ioHelper.GetUmbracoMvcArea();
+            var umbracoPath = globalSettings.GetUmbracoMvcArea(hostingEnvironment);
 
             // create the front-end route
             var defaultRoute = RouteTable.Routes.MapRoute(
@@ -133,10 +134,10 @@ namespace Umbraco.Web.Runtime
             RouteTable.Routes.RegisterArea<UmbracoInstallArea>();
 
             // register all back office routes
-            RouteTable.Routes.RegisterArea(new BackOfficeArea(ioHelper));
+            RouteTable.Routes.RegisterArea(new BackOfficeArea(globalSettings, hostingEnvironment));
 
             // plugin controllers must come first because the next route will catch many things
-            RoutePluginControllers(globalSettings, surfaceControllerTypes, apiControllerTypes, ioHelper);
+            RoutePluginControllers(globalSettings, surfaceControllerTypes, apiControllerTypes, hostingEnvironment);
         }
 
         private static void RouteNoContentController(string umbracoPath)
@@ -151,9 +152,9 @@ namespace Umbraco.Web.Runtime
             IGlobalSettings globalSettings,
             SurfaceControllerTypeCollection surfaceControllerTypes,
             UmbracoApiControllerTypeCollection apiControllerTypes,
-            IIOHelper ioHelper)
+            IHostingEnvironment hostingEnvironment)
         {
-            var umbracoPath = ioHelper.GetUmbracoMvcArea();
+            var umbracoPath = globalSettings.GetUmbracoMvcArea(hostingEnvironment);
 
             // need to find the plugin controllers and route them
             var pluginControllers = surfaceControllerTypes.Concat(apiControllerTypes).ToArray();
@@ -175,7 +176,7 @@ namespace Umbraco.Web.Runtime
             foreach (var g in groupedAreas)
             {
                 // create & register an area for the controllers (this will throw an exception if all controllers are not in the same area)
-                var pluginControllerArea = new PluginControllerArea(globalSettings, ioHelper, g.Select(PluginController.GetMetadata));
+                var pluginControllerArea = new PluginControllerArea(globalSettings, hostingEnvironment, g.Select(PluginController.GetMetadata));
                 RouteTable.Routes.RegisterArea(pluginControllerArea);
             }
         }
diff --git a/src/Umbraco.Web/Security/AppBuilderExtensions.cs b/src/Umbraco.Web/Security/AppBuilderExtensions.cs
index b3f950433c..c2f7c00b35 100644
--- a/src/Umbraco.Web/Security/AppBuilderExtensions.cs
+++ b/src/Umbraco.Web/Security/AppBuilderExtensions.cs
@@ -14,6 +14,7 @@ using Umbraco.Core;
 using Umbraco.Core.Cache;
 using Umbraco.Core.Configuration;
 using Umbraco.Core.Configuration.UmbracoSettings;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.IO;
 using Umbraco.Core.Mapping;
 using Umbraco.Core.Models.Identity;
@@ -36,9 +37,11 @@ namespace Umbraco.Web.Security
         /// </summary>
         /// <param name="app"></param>
         /// <param name="services"></param>
+        /// <param name="mapper"></param>
         /// <param name="contentSettings"></param>
         /// <param name="globalSettings"></param>
-        /// <param name="userMembershipProvider"></param>
+        /// <param name="passwordConfiguration"></param>
+        /// <param name="ipResolver"></param>
         public static void ConfigureUserManagerForUmbracoBackOffice(this IAppBuilder app,
             ServiceContext services,
             UmbracoMapper mapper,
@@ -75,9 +78,9 @@ namespace Umbraco.Web.Security
         /// <param name="app"></param>
         /// <param name="runtimeState"></param>
         /// <param name="globalSettings"></param>
-        /// <param name="userMembershipProvider"></param>
         /// <param name="customUserStore"></param>
         /// <param name="contentSettings"></param>
+        /// <param name="passwordConfiguration"></param>
         /// <param name="ipResolver"></param>
         public static void ConfigureUserManagerForUmbracoBackOffice(this IAppBuilder app,
             IRuntimeState runtimeState,
@@ -143,6 +146,8 @@ namespace Umbraco.Web.Security
         /// <param name="userService"></param>
         /// <param name="globalSettings"></param>
         /// <param name="securitySettings"></param>
+        /// <param name="hostingEnvironment"></param>
+        /// <param name="requestCache"></param>
         /// <returns></returns>
         /// <remarks>
         /// By default this will be configured to execute on PipelineStage.Authenticate
@@ -153,10 +158,10 @@ namespace Umbraco.Web.Security
             IUserService userService,
             IGlobalSettings globalSettings,
             ISecuritySettings securitySettings,
-            IIOHelper ioHelper,
+            IHostingEnvironment hostingEnvironment,
             IRequestCache requestCache)
         {
-            return app.UseUmbracoBackOfficeCookieAuthentication(umbracoContextAccessor, runtimeState, userService, globalSettings, securitySettings, ioHelper, requestCache, PipelineStage.Authenticate);
+            return app.UseUmbracoBackOfficeCookieAuthentication(umbracoContextAccessor, runtimeState, userService, globalSettings, securitySettings, hostingEnvironment, requestCache, PipelineStage.Authenticate);
         }
 
         /// <summary>
@@ -168,7 +173,8 @@ namespace Umbraco.Web.Security
         /// <param name="userService"></param>
         /// <param name="globalSettings"></param>
         /// <param name="securitySettings"></param>
-        /// <param name="ioHelper"></param>
+        /// <param name="hostingEnvironment"></param>
+        /// <param name="requestCache"></param>
         /// <param name="stage">
         /// Configurable pipeline stage
         /// </param>
@@ -179,14 +185,14 @@ namespace Umbraco.Web.Security
             IUserService userService,
             IGlobalSettings globalSettings,
             ISecuritySettings securitySettings,
-            IIOHelper ioHelper,
+            IHostingEnvironment hostingEnvironment,
             IRequestCache requestCache,
             PipelineStage stage)
         {
             //Create the default options and provider
-            var authOptions = app.CreateUmbracoCookieAuthOptions(umbracoContextAccessor, globalSettings, runtimeState, securitySettings, ioHelper, requestCache);
+            var authOptions = app.CreateUmbracoCookieAuthOptions(umbracoContextAccessor, globalSettings, runtimeState, securitySettings, hostingEnvironment, requestCache);
 
-            authOptions.Provider = new BackOfficeCookieAuthenticationProvider(userService, runtimeState, globalSettings, ioHelper, securitySettings)
+            authOptions.Provider = new BackOfficeCookieAuthenticationProvider(userService, runtimeState, globalSettings, hostingEnvironment, securitySettings)
             {
                 // Enables the application to validate the security stamp when the user
                 // logs in. This is a security feature which is used when you
@@ -199,7 +205,7 @@ namespace Umbraco.Web.Security
 
             };
 
-            return app.UseUmbracoBackOfficeCookieAuthentication(umbracoContextAccessor, runtimeState, globalSettings, securitySettings, ioHelper, requestCache, authOptions, stage);
+            return app.UseUmbracoBackOfficeCookieAuthentication(umbracoContextAccessor, runtimeState, globalSettings, securitySettings, hostingEnvironment, requestCache, authOptions, stage);
         }
 
         /// <summary>
@@ -210,14 +216,15 @@ namespace Umbraco.Web.Security
         /// <param name="runtimeState"></param>
         /// <param name="globalSettings"></param>
         /// <param name="securitySettings"></param>
-        /// <param name="ioHelper"></param>
+        /// <param name="hostingEnvironment"></param>
+        /// <param name="requestCache"></param>
         /// <param name="cookieOptions">Custom auth cookie options can be specified to have more control over the cookie authentication logic</param>
         /// <param name="stage">
         /// Configurable pipeline stage
         /// </param>
         /// <returns></returns>
         public static IAppBuilder UseUmbracoBackOfficeCookieAuthentication(this IAppBuilder app, IUmbracoContextAccessor umbracoContextAccessor, IRuntimeState runtimeState, IGlobalSettings globalSettings,
-            ISecuritySettings securitySettings, IIOHelper ioHelper, IRequestCache requestCache, CookieAuthenticationOptions cookieOptions, PipelineStage stage)
+            ISecuritySettings securitySettings, IHostingEnvironment hostingEnvironment, IRequestCache requestCache, CookieAuthenticationOptions cookieOptions, PipelineStage stage)
         {
             if (app == null) throw new ArgumentNullException(nameof(app));
             if (runtimeState == null) throw new ArgumentNullException(nameof(runtimeState));
@@ -232,10 +239,11 @@ namespace Umbraco.Web.Security
             //don't apply if app is not ready
             if (runtimeState.Level != RuntimeLevel.Upgrade && runtimeState.Level != RuntimeLevel.Run) return app;
 
+            var backOfficePath = globalSettings.GetBackOfficePath(hostingEnvironment);
             var cookieAuthOptions = app.CreateUmbracoCookieAuthOptions(
                 umbracoContextAccessor, globalSettings, runtimeState, securitySettings,
                 //This defines the explicit path read cookies from for this middleware
-                ioHelper, requestCache, new[] {$"{ioHelper.BackOfficePath}/backoffice/UmbracoApi/Authentication/GetRemainingTimeoutSeconds"});
+                hostingEnvironment, requestCache, new[] {$"{backOfficePath}/backoffice/UmbracoApi/Authentication/GetRemainingTimeoutSeconds"});
             cookieAuthOptions.Provider = cookieOptions.Provider;
 
             //This is a custom middleware, we need to return the user's remaining logged in seconds
@@ -310,13 +318,15 @@ namespace Umbraco.Web.Security
         /// <param name="umbracoContextAccessor"></param>
         /// <param name="runtimeState"></param>
         /// <param name="globalSettings"></param>
+        /// <param name="hostingEnvironment"></param>
+        /// <param name="requestCache"></param>
         /// <returns></returns>
         /// <remarks>
         /// By default this will be configured to execute on PipelineStage.Authenticate
         /// </remarks>
-        public static IAppBuilder UseUmbracoBackOfficeExternalCookieAuthentication(this IAppBuilder app, IUmbracoContextAccessor umbracoContextAccessor, IRuntimeState runtimeState,IGlobalSettings globalSettings, IIOHelper ioHelper, IRequestCache requestCache)
+        public static IAppBuilder UseUmbracoBackOfficeExternalCookieAuthentication(this IAppBuilder app, IUmbracoContextAccessor umbracoContextAccessor, IRuntimeState runtimeState,IGlobalSettings globalSettings, IHostingEnvironment hostingEnvironment, IRequestCache requestCache)
         {
-            return app.UseUmbracoBackOfficeExternalCookieAuthentication(umbracoContextAccessor, runtimeState, globalSettings, ioHelper, requestCache, PipelineStage.Authenticate);
+            return app.UseUmbracoBackOfficeExternalCookieAuthentication(umbracoContextAccessor, runtimeState, globalSettings, hostingEnvironment, requestCache, PipelineStage.Authenticate);
         }
 
         /// <summary>
@@ -327,16 +337,17 @@ namespace Umbraco.Web.Security
         /// <param name="umbracoContextAccessor"></param>
         /// <param name="runtimeState"></param>
         /// <param name="globalSettings"></param>
-        /// <param name="ioHelper"></param>
+        /// <param name="hostingEnvironment"></param>
+        /// <param name="requestCache"></param>
         /// <param name="stage"></param>
         /// <returns></returns>
         public static IAppBuilder UseUmbracoBackOfficeExternalCookieAuthentication(this IAppBuilder app,
             IUmbracoContextAccessor umbracoContextAccessor, IRuntimeState runtimeState,
-            IGlobalSettings globalSettings, IIOHelper ioHelper, IRequestCache requestCache, PipelineStage stage)
+            IGlobalSettings globalSettings, IHostingEnvironment hostingEnvironment, IRequestCache requestCache, PipelineStage stage)
         {
             if (app == null) throw new ArgumentNullException(nameof(app));
             if (runtimeState == null) throw new ArgumentNullException(nameof(runtimeState));
-            if (ioHelper == null) throw new ArgumentNullException(nameof(ioHelper));
+            if (hostingEnvironment == null) throw new ArgumentNullException(nameof(hostingEnvironment));
 
             app.UseCookieAuthentication(new CookieAuthenticationOptions
             {
@@ -345,7 +356,7 @@ namespace Umbraco.Web.Security
                 CookieName = Constants.Security.BackOfficeExternalCookieName,
                 ExpireTimeSpan = TimeSpan.FromMinutes(5),
                 //Custom cookie manager so we can filter requests
-                CookieManager = new BackOfficeCookieManager(umbracoContextAccessor, runtimeState, ioHelper, requestCache),
+                CookieManager = new BackOfficeCookieManager(umbracoContextAccessor, runtimeState, hostingEnvironment, globalSettings, requestCache),
                 CookiePath = "/",
                 CookieSecure = globalSettings.UseHttps ? CookieSecureOption.Always : CookieSecureOption.SameAsRequest,
                 CookieHttpOnly = true,
@@ -364,6 +375,8 @@ namespace Umbraco.Web.Security
         /// <param name="globalSettings"></param>
         /// <param name="securitySettings"></param>
         /// <param name="ioHelper"></param>
+        /// <param name="hostingEnvironment"></param>
+        /// <param name="requestCache"></param>
         /// <returns></returns>
         /// <remarks>
         /// This ensures that during a preview request that the back office use is also Authenticated and that the back office Identity
@@ -372,9 +385,9 @@ namespace Umbraco.Web.Security
         /// <remarks>
         /// By default this will be configured to execute on PipelineStage.PostAuthenticate
         /// </remarks>
-        public static IAppBuilder UseUmbracoPreviewAuthentication(this IAppBuilder app, IUmbracoContextAccessor umbracoContextAccessor, IRuntimeState runtimeState, IGlobalSettings globalSettings, ISecuritySettings securitySettings, IIOHelper ioHelper, IRequestCache requestCache)
+        public static IAppBuilder UseUmbracoPreviewAuthentication(this IAppBuilder app, IUmbracoContextAccessor umbracoContextAccessor, IRuntimeState runtimeState, IGlobalSettings globalSettings, ISecuritySettings securitySettings, IHostingEnvironment hostingEnvironment, IRequestCache requestCache)
         {
-            return app.UseUmbracoPreviewAuthentication(umbracoContextAccessor, runtimeState, globalSettings, securitySettings, ioHelper, requestCache, PipelineStage.PostAuthenticate);
+            return app.UseUmbracoPreviewAuthentication(umbracoContextAccessor, runtimeState, globalSettings, securitySettings, hostingEnvironment, requestCache, PipelineStage.PostAuthenticate);
         }
 
         /// <summary>
@@ -386,18 +399,20 @@ namespace Umbraco.Web.Security
         /// <param name="globalSettings"></param>
         /// <param name="securitySettings"></param>
         /// <param name="ioHelper"></param>
+        /// <param name="hostingEnvironment"></param>
+        /// <param name="requestCache"></param>
         /// <param name="stage"></param>
         /// <returns></returns>
         /// <remarks>
         /// This ensures that during a preview request that the back office use is also Authenticated and that the back office Identity
         /// is added as a secondary identity to the current IPrincipal so it can be used to Authorize the previewed document.
         /// </remarks>
-        public static IAppBuilder UseUmbracoPreviewAuthentication(this IAppBuilder app, IUmbracoContextAccessor umbracoContextAccessor, IRuntimeState runtimeState, IGlobalSettings globalSettings, ISecuritySettings securitySettings, IIOHelper ioHelper, IRequestCache requestCache, PipelineStage stage)
+        public static IAppBuilder UseUmbracoPreviewAuthentication(this IAppBuilder app, IUmbracoContextAccessor umbracoContextAccessor, IRuntimeState runtimeState, IGlobalSettings globalSettings, ISecuritySettings securitySettings, IHostingEnvironment hostingEnvironment, IRequestCache requestCache, PipelineStage stage)
         {
             if (runtimeState.Level != RuntimeLevel.Run) return app;
 
-            var authOptions = app.CreateUmbracoCookieAuthOptions(umbracoContextAccessor, globalSettings, runtimeState, securitySettings, ioHelper, requestCache);
-            app.Use(typeof(PreviewAuthenticationMiddleware),  authOptions, ioHelper);
+            var authOptions = app.CreateUmbracoCookieAuthOptions(umbracoContextAccessor, globalSettings, runtimeState, securitySettings, hostingEnvironment, requestCache);
+            app.Use(typeof(PreviewAuthenticationMiddleware), authOptions, globalSettings, hostingEnvironment);
 
             // This middleware must execute at least on PostAuthentication, by default it is on Authorize
             // The middleware needs to execute after the RoleManagerModule executes which is during PostAuthenticate,
@@ -423,11 +438,13 @@ namespace Umbraco.Web.Security
         /// <param name="globalSettings"></param>
         /// <param name="runtimeState"></param>
         /// <param name="securitySettings"></param>
+        /// <param name="hostingEnvironment"></param>
+        /// <param name="requestCache"></param>
         /// <param name="explicitPaths"></param>
         /// <returns></returns>
         public static UmbracoBackOfficeCookieAuthOptions CreateUmbracoCookieAuthOptions(this IAppBuilder app,
             IUmbracoContextAccessor umbracoContextAccessor,
-            IGlobalSettings globalSettings, IRuntimeState runtimeState, ISecuritySettings securitySettings, IIOHelper ioHelper, IRequestCache requestCache, string[] explicitPaths = null)
+            IGlobalSettings globalSettings, IRuntimeState runtimeState, ISecuritySettings securitySettings, IHostingEnvironment hostingEnvironment, IRequestCache requestCache, string[] explicitPaths = null)
         {
             //this is how aspnet wires up the default AuthenticationTicket protector so we'll use the same code
             var ticketDataFormat = new TicketDataFormat(
@@ -440,9 +457,9 @@ namespace Umbraco.Web.Security
                 umbracoContextAccessor,
                 securitySettings,
                 globalSettings,
+                hostingEnvironment,
                 runtimeState,
                 ticketDataFormat,
-                ioHelper,
                 requestCache);
 
             return authOptions;
diff --git a/src/Umbraco.Web/Security/BackOfficeCookieAuthenticationProvider.cs b/src/Umbraco.Web/Security/BackOfficeCookieAuthenticationProvider.cs
index 59b20bdd75..8290b8f9b7 100644
--- a/src/Umbraco.Web/Security/BackOfficeCookieAuthenticationProvider.cs
+++ b/src/Umbraco.Web/Security/BackOfficeCookieAuthenticationProvider.cs
@@ -11,6 +11,7 @@ using Umbraco.Core.IO;
 using Umbraco.Core.Security;
 using Umbraco.Core.Services;
 using Umbraco.Core.Configuration.UmbracoSettings;
+using Umbraco.Core.Hosting;
 
 namespace Umbraco.Web.Security
 {
@@ -19,15 +20,15 @@ namespace Umbraco.Web.Security
         private readonly IUserService _userService;
         private readonly IRuntimeState _runtimeState;
         private readonly IGlobalSettings _globalSettings;
-        private readonly IIOHelper _ioHelper;
+        private readonly IHostingEnvironment _hostingEnvironment;
         private readonly ISecuritySettings _securitySettings;
 
-        public BackOfficeCookieAuthenticationProvider(IUserService userService, IRuntimeState runtimeState, IGlobalSettings globalSettings, IIOHelper ioHelper, ISecuritySettings securitySettings)
+        public BackOfficeCookieAuthenticationProvider(IUserService userService, IRuntimeState runtimeState, IGlobalSettings globalSettings, IHostingEnvironment hostingEnvironment, ISecuritySettings securitySettings)
         {
             _userService = userService;
             _runtimeState = runtimeState;
             _globalSettings = globalSettings;
-            _ioHelper = ioHelper;
+            _hostingEnvironment = hostingEnvironment;
             _securitySettings = securitySettings;
         }
 
@@ -118,7 +119,7 @@ namespace Umbraco.Web.Security
         protected virtual async Task EnsureValidSessionId(CookieValidateIdentityContext context)
         {
             if (_runtimeState.Level == RuntimeLevel.Run)
-                await SessionIdValidator.ValidateSessionAsync(TimeSpan.FromMinutes(1), context, _globalSettings, _ioHelper);
+                await SessionIdValidator.ValidateSessionAsync(TimeSpan.FromMinutes(1), context, _globalSettings, _hostingEnvironment);
         }
 
 
diff --git a/src/Umbraco.Web/Security/BackOfficeCookieManager.cs b/src/Umbraco.Web/Security/BackOfficeCookieManager.cs
index 17c5f1befb..435396cac9 100644
--- a/src/Umbraco.Web/Security/BackOfficeCookieManager.cs
+++ b/src/Umbraco.Web/Security/BackOfficeCookieManager.cs
@@ -7,6 +7,7 @@ using Microsoft.Owin.Infrastructure;
 using Umbraco.Core;
 using Umbraco.Core.Cache;
 using Umbraco.Core.Configuration;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.IO;
 using Umbraco.Core.Security;
 
@@ -23,23 +24,26 @@ namespace Umbraco.Web.Security
     {
         private readonly IUmbracoContextAccessor _umbracoContextAccessor;
         private readonly IRuntimeState _runtime;
-        private readonly IIOHelper _ioHelper;
+        private readonly IHostingEnvironment _hostingEnvironment;
+        private readonly IGlobalSettings _globalSettings;
         private readonly IRequestCache _requestCache;
         private readonly string[] _explicitPaths;
         private readonly string _getRemainingSecondsPath;
 
-        public BackOfficeCookieManager(IUmbracoContextAccessor umbracoContextAccessor, IRuntimeState runtime, IIOHelper ioHelper, IRequestCache requestCache)
-            : this(umbracoContextAccessor, runtime, ioHelper,requestCache, null)
+        public BackOfficeCookieManager(IUmbracoContextAccessor umbracoContextAccessor, IRuntimeState runtime, IHostingEnvironment hostingEnvironment, IGlobalSettings globalSettings, IRequestCache requestCache)
+            : this(umbracoContextAccessor, runtime, hostingEnvironment, globalSettings, requestCache, null)
         { }
 
-        public BackOfficeCookieManager(IUmbracoContextAccessor umbracoContextAccessor, IRuntimeState runtime,  IIOHelper ioHelper, IRequestCache requestCache, IEnumerable<string> explicitPaths)
+        public BackOfficeCookieManager(IUmbracoContextAccessor umbracoContextAccessor, IRuntimeState runtime,  IHostingEnvironment hostingEnvironment, IGlobalSettings globalSettings, IRequestCache requestCache, IEnumerable<string> explicitPaths)
         {
             _umbracoContextAccessor = umbracoContextAccessor;
             _runtime = runtime;
-            _ioHelper = ioHelper;
+            _hostingEnvironment = hostingEnvironment;
+            _globalSettings = globalSettings;
             _requestCache = requestCache;
             _explicitPaths = explicitPaths?.ToArray();
-            _getRemainingSecondsPath = $"{ioHelper.BackOfficePath}/backoffice/UmbracoApi/Authentication/GetRemainingTimeoutSeconds";
+            var backOfficePath = _globalSettings.GetBackOfficePath(_hostingEnvironment);
+            _getRemainingSecondsPath = $"{backOfficePath}/backoffice/UmbracoApi/Authentication/GetRemainingTimeoutSeconds";
         }
 
         /// <summary>
@@ -103,9 +107,9 @@ namespace Umbraco.Web.Security
                 (checkForceAuthTokens && owinContext.Get<bool?>(Constants.Security.ForceReAuthFlag) != null)
                 || (checkForceAuthTokens && _requestCache.IsAvailable && _requestCache.Get(Constants.Security.ForceReAuthFlag) != null)
                 //check back office
-                || request.Uri.IsBackOfficeRequest(HttpRuntime.AppDomainAppVirtualPath, _ioHelper)
+                || request.Uri.IsBackOfficeRequest(_globalSettings, _hostingEnvironment)
                 //check installer
-                || request.Uri.IsInstallerRequest(_ioHelper))
+                || request.Uri.IsInstallerRequest(_hostingEnvironment))
             {
                 return true;
             }
diff --git a/src/Umbraco.Web/Security/GetUserSecondsMiddleWare.cs b/src/Umbraco.Web/Security/GetUserSecondsMiddleWare.cs
index 448ec88915..f6b8fa765d 100644
--- a/src/Umbraco.Web/Security/GetUserSecondsMiddleWare.cs
+++ b/src/Umbraco.Web/Security/GetUserSecondsMiddleWare.cs
@@ -8,6 +8,7 @@ using Microsoft.Owin.Logging;
 using Umbraco.Core;
 using Umbraco.Core.Configuration;
 using Umbraco.Core.Configuration.UmbracoSettings;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.IO;
 using Umbraco.Core.Security;
 
@@ -27,7 +28,7 @@ namespace Umbraco.Web.Security
         private readonly IGlobalSettings _globalSettings;
         private readonly ISecuritySettings _security;
         private readonly ILogger _logger;
-        private readonly IIOHelper _ioHelper;
+        private readonly IHostingEnvironment _hostingEnvironment;
 
         public GetUserSecondsMiddleWare(
             OwinMiddleware next,
@@ -35,14 +36,14 @@ namespace Umbraco.Web.Security
             IGlobalSettings globalSettings,
             ISecuritySettings security,
             ILogger logger,
-            IIOHelper ioHelper)
+            IHostingEnvironment hostingEnvironment)
             : base(next)
         {
             _authOptions = authOptions ?? throw new ArgumentNullException(nameof(authOptions));
             _globalSettings = globalSettings;
             _security = security;
             _logger = logger ?? throw new ArgumentNullException(nameof(logger));
-            _ioHelper = ioHelper;
+            _hostingEnvironment = hostingEnvironment;
         }
 
         public override async Task Invoke(IOwinContext context)
@@ -52,7 +53,7 @@ namespace Umbraco.Web.Security
 
             if (request.Uri.Scheme.InvariantStartsWith("http")
                 && request.Uri.AbsolutePath.InvariantEquals(
-                    $"{_ioHelper.BackOfficePath}/backoffice/UmbracoApi/Authentication/GetRemainingTimeoutSeconds"))
+                    $"{_globalSettings.GetBackOfficePath(_hostingEnvironment)}/backoffice/UmbracoApi/Authentication/GetRemainingTimeoutSeconds"))
             {
                 var cookie = _authOptions.CookieManager.GetRequestCookie(context, _security.AuthCookieName);
                 if (cookie.IsNullOrWhiteSpace() == false)
diff --git a/src/Umbraco.Web/Security/PreviewAuthenticationMiddleware.cs b/src/Umbraco.Web/Security/PreviewAuthenticationMiddleware.cs
index c73cd061c9..2f9648d1f7 100644
--- a/src/Umbraco.Web/Security/PreviewAuthenticationMiddleware.cs
+++ b/src/Umbraco.Web/Security/PreviewAuthenticationMiddleware.cs
@@ -4,6 +4,7 @@ using System.Web;
 using Microsoft.Owin;
 using Umbraco.Core;
 using Umbraco.Core.Configuration;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.IO;
 using Umbraco.Core.Security;
 
@@ -12,7 +13,8 @@ namespace Umbraco.Web.Security
     internal class PreviewAuthenticationMiddleware : OwinMiddleware
     {
         private readonly UmbracoBackOfficeCookieAuthOptions _cookieOptions;
-        private readonly IIOHelper _ioHelper;
+        private readonly IGlobalSettings _globalSettings;
+        private readonly IHostingEnvironment _hostingEnvironment;
 
         /// <summary>
         /// Instantiates the middleware with an optional pointer to the next component.
@@ -20,11 +22,13 @@ namespace Umbraco.Web.Security
         /// <param name="next"/>
         /// <param name="cookieOptions"></param>
         /// <param name="globalSettings"></param>
+        /// <param name="hostingEnvironment"></param>
         public PreviewAuthenticationMiddleware(OwinMiddleware next,
-            UmbracoBackOfficeCookieAuthOptions cookieOptions, IIOHelper ioHelper) : base(next)
+            UmbracoBackOfficeCookieAuthOptions cookieOptions, IGlobalSettings globalSettings, IHostingEnvironment hostingEnvironment) : base(next)
         {
             _cookieOptions = cookieOptions;
-            _ioHelper = ioHelper;
+            _globalSettings = globalSettings;
+            _hostingEnvironment = hostingEnvironment;
         }
 
         /// <summary>
@@ -41,7 +45,7 @@ namespace Umbraco.Web.Security
                 var isPreview = request.HasPreviewCookie()
                     && claimsPrincipal != null
                     && request.Uri != null
-                    && request.Uri.IsBackOfficeRequest(HttpRuntime.AppDomainAppVirtualPath, _ioHelper) == false;
+                    && request.Uri.IsBackOfficeRequest(_globalSettings, _hostingEnvironment) == false;
                 if (isPreview)
                 {
                     //If we've gotten this far it means a preview cookie has been set and a front-end umbraco document request is executing.
diff --git a/src/Umbraco.Web/Security/SessionIdValidator.cs b/src/Umbraco.Web/Security/SessionIdValidator.cs
index 2339bff7f6..cd3dd457d0 100644
--- a/src/Umbraco.Web/Security/SessionIdValidator.cs
+++ b/src/Umbraco.Web/Security/SessionIdValidator.cs
@@ -9,6 +9,7 @@ using Microsoft.Owin.Infrastructure;
 using Microsoft.Owin.Security.Cookies;
 using Umbraco.Core;
 using Umbraco.Core.Configuration;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.IO;
 
 using Constants = Umbraco.Core.Constants;
@@ -29,9 +30,9 @@ namespace Umbraco.Web.Security
     {
         public const string CookieName = "UMB_UCONTEXT_C";
 
-        public static async Task ValidateSessionAsync(TimeSpan validateInterval, CookieValidateIdentityContext context, IGlobalSettings globalSettings, IIOHelper ioHelper)
+        public static async Task ValidateSessionAsync(TimeSpan validateInterval, CookieValidateIdentityContext context, IGlobalSettings globalSettings, IHostingEnvironment hostingEnvironment)
         {
-            if (context.Request.Uri.IsBackOfficeRequest(HttpRuntime.AppDomainAppVirtualPath, ioHelper) == false)
+            if (context.Request.Uri.IsBackOfficeRequest(globalSettings, hostingEnvironment) == false)
                 return;
 
             var valid = await ValidateSessionAsync(validateInterval, context.OwinContext, context.Options.CookieManager, context.Options.SystemClock, context.Properties.IssuedUtc, context.Identity, globalSettings);
diff --git a/src/Umbraco.Web/Security/UmbracoBackOfficeCookieAuthOptions.cs b/src/Umbraco.Web/Security/UmbracoBackOfficeCookieAuthOptions.cs
index 5e8bdffbed..68155f47b7 100644
--- a/src/Umbraco.Web/Security/UmbracoBackOfficeCookieAuthOptions.cs
+++ b/src/Umbraco.Web/Security/UmbracoBackOfficeCookieAuthOptions.cs
@@ -6,6 +6,7 @@ using Umbraco.Core;
 using Umbraco.Core.Cache;
 using Umbraco.Core.Configuration;
 using Umbraco.Core.Configuration.UmbracoSettings;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.IO;
 
 namespace Umbraco.Web.Security
@@ -22,9 +23,9 @@ namespace Umbraco.Web.Security
             IUmbracoContextAccessor umbracoContextAccessor,
             ISecuritySettings securitySettings,
             IGlobalSettings globalSettings,
+            IHostingEnvironment hostingEnvironment,
             IRuntimeState runtimeState,
             ISecureDataFormat<AuthenticationTicket> secureDataFormat,
-            IIOHelper ioHelper,
             IRequestCache requestCache)
         {
             var secureDataFormat1 = secureDataFormat ?? throw new ArgumentNullException(nameof(secureDataFormat));
@@ -42,7 +43,7 @@ namespace Umbraco.Web.Security
             TicketDataFormat = new UmbracoSecureDataFormat(LoginTimeoutMinutes, secureDataFormat1);
 
             //Custom cookie manager so we can filter requests
-            CookieManager = new BackOfficeCookieManager(umbracoContextAccessor, runtimeState, ioHelper, requestCache, explicitPaths);
+            CookieManager = new BackOfficeCookieManager(umbracoContextAccessor, runtimeState, hostingEnvironment, globalSettings, requestCache, explicitPaths);
         }
 
         /// <summary>
diff --git a/src/Umbraco.Web/Security/WebSecurity.cs b/src/Umbraco.Web/Security/WebSecurity.cs
index 6f16eb3c52..4538666374 100644
--- a/src/Umbraco.Web/Security/WebSecurity.cs
+++ b/src/Umbraco.Web/Security/WebSecurity.cs
@@ -8,6 +8,7 @@ using Umbraco.Core.Models.Membership;
 using Microsoft.AspNet.Identity.Owin;
 using Microsoft.Owin;
 using Umbraco.Core.Configuration;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.IO;
 using Umbraco.Core.Models;
 using Umbraco.Web.Models.Identity;
@@ -23,14 +24,14 @@ namespace Umbraco.Web.Security
         private readonly IHttpContextAccessor _httpContextAccessor;
         private readonly IUserService _userService;
         private readonly IGlobalSettings _globalSettings;
-        private readonly IIOHelper _ioHelper;
+        private readonly IHostingEnvironment _hostingEnvironment;
 
-        public WebSecurity(IHttpContextAccessor httpContextAccessor, IUserService userService, IGlobalSettings globalSettings, IIOHelper ioHelper)
+        public WebSecurity(IHttpContextAccessor httpContextAccessor, IUserService userService, IGlobalSettings globalSettings, IHostingEnvironment hostingEnvironment)
         {
             _httpContextAccessor = httpContextAccessor;
             _userService = userService;
             _globalSettings = globalSettings;
-            _ioHelper = ioHelper;
+            _hostingEnvironment = hostingEnvironment;
         }
 
         private IUser _currentUser;
@@ -145,7 +146,7 @@ namespace Umbraco.Web.Security
             var user = CurrentUser;
 
             // Check for console access
-            if (user == null || (requiresApproval && user.IsApproved == false) || (user.IsLockedOut && RequestIsInUmbracoApplication(_httpContextAccessor, _globalSettings, _ioHelper)))
+            if (user == null || (requiresApproval && user.IsApproved == false) || (user.IsLockedOut && RequestIsInUmbracoApplication(_httpContextAccessor, _globalSettings, _hostingEnvironment)))
             {
                 if (throwExceptions) throw new ArgumentException("You have no privileges to the umbraco console. Please contact your administrator");
                 return ValidateRequestAttempt.FailedNoPrivileges;
@@ -154,9 +155,9 @@ namespace Umbraco.Web.Security
 
         }
 
-        private static bool RequestIsInUmbracoApplication(IHttpContextAccessor httpContextAccessor, IGlobalSettings globalSettings, IIOHelper ioHelper)
+        private static bool RequestIsInUmbracoApplication(IHttpContextAccessor httpContextAccessor, IGlobalSettings globalSettings, IHostingEnvironment hostingEnvironment)
         {
-            return httpContextAccessor.GetRequiredHttpContext().Request.Path.ToLower().IndexOf(ioHelper.ResolveUrl(globalSettings.UmbracoPath).ToLower(), StringComparison.Ordinal) > -1;
+            return httpContextAccessor.GetRequiredHttpContext().Request.Path.ToLower().IndexOf(hostingEnvironment.ToAbsolute(globalSettings.UmbracoPath).ToLower(), StringComparison.Ordinal) > -1;
         }
 
         /// <summary>
diff --git a/src/Umbraco.Web/UmbracoContext.cs b/src/Umbraco.Web/UmbracoContext.cs
index de3231fe2c..24b302bbbe 100644
--- a/src/Umbraco.Web/UmbracoContext.cs
+++ b/src/Umbraco.Web/UmbracoContext.cs
@@ -3,6 +3,7 @@ using System.Web;
 using Umbraco.Core;
 using Umbraco.Core.Configuration;
 using Umbraco.Core.Cookie;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.IO;
 using Umbraco.Core.Models.PublishedContent;
 using Umbraco.Web.Composing;
@@ -19,8 +20,7 @@ namespace Umbraco.Web
     {
         private readonly IHttpContextAccessor _httpContextAccessor;
         private readonly IGlobalSettings _globalSettings;
-        private readonly IIOHelper _ioHelper;
-        private readonly UriUtility _uriUtility;
+        private readonly IHostingEnvironment _hostingEnvironment;
         private readonly ICookieManager _cookieManager;
         private readonly Lazy<IPublishedSnapshot> _publishedSnapshot;
         private string _previewToken;
@@ -34,8 +34,8 @@ namespace Umbraco.Web
             IPublishedSnapshotService publishedSnapshotService,
             IWebSecurity webSecurity,
             IGlobalSettings globalSettings,
+            IHostingEnvironment hostingEnvironment,
             IVariationContextAccessor variationContextAccessor,
-            IIOHelper ioHelper,
             UriUtility uriUtility,
             ICookieManager cookieManager)
         {
@@ -45,8 +45,7 @@ namespace Umbraco.Web
             VariationContextAccessor = variationContextAccessor ??  throw new ArgumentNullException(nameof(variationContextAccessor));
             _httpContextAccessor = httpContextAccessor;
             _globalSettings = globalSettings ?? throw new ArgumentNullException(nameof(globalSettings));
-            _ioHelper = ioHelper ?? throw new ArgumentNullException(nameof(ioHelper));
-            _uriUtility = uriUtility;
+            _hostingEnvironment = hostingEnvironment;
             _cookieManager = cookieManager;
 
             // ensure that this instance is disposed when the request terminates, though we *also* ensure
@@ -74,7 +73,7 @@ namespace Umbraco.Web
             // see: http://issues.umbraco.org/issue/U4-1890
             //
             OriginalRequestUrl = GetRequestFromContext()?.Url ?? new Uri("http://localhost");
-            CleanedUmbracoUrl = _uriUtility.UriToUmbraco(OriginalRequestUrl);
+            CleanedUmbracoUrl = uriUtility.UriToUmbraco(OriginalRequestUrl);
         }
 
         /// <summary>
@@ -184,7 +183,7 @@ namespace Umbraco.Web
         {
             var request = GetRequestFromContext();
             if (request?.Url != null
-                && request.Url.IsBackOfficeRequest(HttpRuntime.AppDomainAppVirtualPath, _ioHelper) == false
+                && request.Url.IsBackOfficeRequest(_globalSettings, _hostingEnvironment) == false
                 && Security.CurrentUser != null)
             {
                 var previewToken = _cookieManager.GetPreviewCookieValue(); // may be null or empty
diff --git a/src/Umbraco.Web/UmbracoContextFactory.cs b/src/Umbraco.Web/UmbracoContextFactory.cs
index 4090da5a6d..73c4877747 100644
--- a/src/Umbraco.Web/UmbracoContextFactory.cs
+++ b/src/Umbraco.Web/UmbracoContextFactory.cs
@@ -3,6 +3,7 @@ using System.IO;
 using System.Text;
 using Umbraco.Core.Configuration;
 using Umbraco.Core.Cookie;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.IO;
 using Umbraco.Core.Models.PublishedContent;
 using Umbraco.Core.Services;
@@ -25,7 +26,7 @@ namespace Umbraco.Web
 
         private readonly IGlobalSettings _globalSettings;
         private readonly IUserService _userService;
-        private readonly IIOHelper _ioHelper;
+        private readonly IHostingEnvironment _hostingEnvironment;
         private readonly IHttpContextAccessor _httpContextAccessor;
         private readonly ICookieManager _cookieManager;
         private readonly UriUtility _uriUtility;
@@ -40,7 +41,7 @@ namespace Umbraco.Web
             IDefaultCultureAccessor defaultCultureAccessor,
             IGlobalSettings globalSettings,
             IUserService userService,
-            IIOHelper ioHelper,
+            IHostingEnvironment hostingEnvironment,
             UriUtility uriUtility,
             IHttpContextAccessor httpContextAccessor,
             ICookieManager cookieManager)
@@ -51,7 +52,7 @@ namespace Umbraco.Web
             _defaultCultureAccessor = defaultCultureAccessor ?? throw new ArgumentNullException(nameof(defaultCultureAccessor));
             _globalSettings = globalSettings ?? throw new ArgumentNullException(nameof(globalSettings));
             _userService = userService ?? throw new ArgumentNullException(nameof(userService));
-            _ioHelper = ioHelper;
+            _hostingEnvironment = hostingEnvironment;
             _uriUtility = uriUtility;
             _httpContextAccessor = httpContextAccessor;
             _cookieManager = cookieManager;
@@ -70,9 +71,9 @@ namespace Umbraco.Web
                 _variationContextAccessor.VariationContext = new VariationContext(_defaultCultureAccessor.DefaultCulture);
             }
 
-            var webSecurity = new WebSecurity(_httpContextAccessor, _userService, _globalSettings, _ioHelper);
+            var webSecurity = new WebSecurity(_httpContextAccessor, _userService, _globalSettings, _hostingEnvironment);
 
-            return new UmbracoContext(_httpContextAccessor, _publishedSnapshotService, webSecurity, _globalSettings, _variationContextAccessor, _ioHelper, _uriUtility, _cookieManager);
+            return new UmbracoContext(_httpContextAccessor, _publishedSnapshotService, webSecurity, _globalSettings, _hostingEnvironment, _variationContextAccessor, _uriUtility, _cookieManager);
         }
 
         /// <inheritdoc />
diff --git a/src/Umbraco.Web/UmbracoDefaultOwinStartup.cs b/src/Umbraco.Web/UmbracoDefaultOwinStartup.cs
index a0b7cdd225..a2b523a64e 100644
--- a/src/Umbraco.Web/UmbracoDefaultOwinStartup.cs
+++ b/src/Umbraco.Web/UmbracoDefaultOwinStartup.cs
@@ -5,6 +5,7 @@ using Umbraco.Core;
 using Umbraco.Core.Cache;
 using Umbraco.Core.Configuration;
 using Umbraco.Core.Configuration.UmbracoSettings;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.IO;
 using Umbraco.Core.Mapping;
 using Umbraco.Net;
@@ -35,7 +36,7 @@ namespace Umbraco.Web
         protected ServiceContext Services => Current.Services;
         protected UmbracoMapper Mapper => Current.Mapper;
         protected IIpResolver IpResolver => Current.IpResolver;
-        protected IIOHelper IOHelper => Current.IOHelper;
+        protected IHostingEnvironment HostingEnvironment => Current.HostingEnvironment;
         protected IRequestCache RequestCache => Current.AppCaches.RequestCache;
 
         /// <summary>
@@ -76,7 +77,7 @@ namespace Umbraco.Web
             ConfigureUmbracoAuthentication(app);
 
             app
-                .UseSignalR(IOHelper)
+                .UseSignalR(GlobalSettings, HostingEnvironment)
                 .FinalizeMiddlewareConfiguration();
         }
 
@@ -105,9 +106,9 @@ namespace Umbraco.Web
             // Ensure owin is configured for Umbraco back office authentication.
             // Front-end OWIN cookie configuration must be declared after this code.
             app
-                .UseUmbracoBackOfficeCookieAuthentication(UmbracoContextAccessor, RuntimeState, Services.UserService, GlobalSettings, SecuritySettings, IOHelper, RequestCache, PipelineStage.Authenticate)
-                .UseUmbracoBackOfficeExternalCookieAuthentication(UmbracoContextAccessor, RuntimeState, GlobalSettings, IOHelper, RequestCache, PipelineStage.Authenticate)
-                .UseUmbracoPreviewAuthentication(UmbracoContextAccessor, RuntimeState, GlobalSettings, SecuritySettings, IOHelper, RequestCache, PipelineStage.Authorize);
+                .UseUmbracoBackOfficeCookieAuthentication(UmbracoContextAccessor, RuntimeState, Services.UserService, GlobalSettings, SecuritySettings, HostingEnvironment, RequestCache, PipelineStage.Authenticate)
+                .UseUmbracoBackOfficeExternalCookieAuthentication(UmbracoContextAccessor, RuntimeState, GlobalSettings, HostingEnvironment, RequestCache, PipelineStage.Authenticate)
+                .UseUmbracoPreviewAuthentication(UmbracoContextAccessor, RuntimeState, GlobalSettings, SecuritySettings, HostingEnvironment, RequestCache, PipelineStage.Authorize);
         }
 
         public static event EventHandler<OwinMiddlewareConfiguredEventArgs> MiddlewareConfigured;
diff --git a/src/Umbraco.Web/UmbracoInjectedModule.cs b/src/Umbraco.Web/UmbracoInjectedModule.cs
index 73e82702a3..99aece5f8c 100644
--- a/src/Umbraco.Web/UmbracoInjectedModule.cs
+++ b/src/Umbraco.Web/UmbracoInjectedModule.cs
@@ -6,6 +6,7 @@ using Umbraco.Core;
 using Umbraco.Core.Cache;
 using Umbraco.Core.Configuration;
 using Umbraco.Core.Exceptions;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.IO;
 using Umbraco.Core.Logging;
 using Umbraco.Web.Composing;
@@ -37,7 +38,8 @@ namespace Umbraco.Web
         private readonly IUmbracoContextFactory _umbracoContextFactory;
         private readonly RoutableDocumentFilter _routableDocumentLookup;
         private readonly IRequestCache _requestCache;
-        private readonly IIOHelper _ioHelper;
+        private readonly IGlobalSettings _globalSettings;
+        private readonly IHostingEnvironment _hostingEnvironment;
         private readonly UriUtility _uriUtility;
 
         public UmbracoInjectedModule(
@@ -48,7 +50,8 @@ namespace Umbraco.Web
             RoutableDocumentFilter routableDocumentLookup,
             UriUtility uriUtility,
             IRequestCache requestCache,
-            IIOHelper ioHelper)
+            IGlobalSettings globalSettings,
+            IHostingEnvironment hostingEnvironment)
         {
             _runtime = runtime;
             _logger = logger;
@@ -57,7 +60,8 @@ namespace Umbraco.Web
             _routableDocumentLookup = routableDocumentLookup;
             _uriUtility = uriUtility;
             _requestCache = requestCache;
-            _ioHelper = ioHelper;
+            _globalSettings = globalSettings;
+            _hostingEnvironment = hostingEnvironment;
         }
 
         #region HttpModule event handlers
@@ -111,7 +115,7 @@ namespace Umbraco.Web
             var umbracoContext = Current.UmbracoContext;
 
             // re-write for the default back office path
-            if (httpContext.Request.Url.IsDefaultBackOfficeRequest(_ioHelper))
+            if (httpContext.Request.Url.IsDefaultBackOfficeRequest(_globalSettings, _hostingEnvironment))
             {
                 if (EnsureRuntime(httpContext, umbracoContext.OriginalRequestUrl))
                     RewriteToBackOfficeHandler(httpContext);
@@ -257,7 +261,7 @@ namespace Umbraco.Web
         private void RewriteToBackOfficeHandler(HttpContextBase context)
         {
             // GlobalSettings.Path has already been through IOHelper.ResolveUrl() so it begins with / and vdir (if any)
-            var rewritePath = _ioHelper.BackOfficePath.TrimEnd('/') + "/Default";
+            var rewritePath = _globalSettings.GetBackOfficePath(_hostingEnvironment).TrimEnd('/') + "/Default";
             // rewrite the path to the path of the handler (i.e. /umbraco/RenderMvc)
             context.RewritePath(rewritePath, "", "", false);
 
@@ -290,7 +294,7 @@ namespace Umbraco.Web
             var query = pcr.Uri.Query.TrimStart('?');
 
             // GlobalSettings.Path has already been through IOHelper.ResolveUrl() so it begins with / and vdir (if any)
-            var rewritePath = _ioHelper.BackOfficePath.TrimEnd('/') + "/RenderMvc";
+            var rewritePath = _globalSettings.GetBackOfficePath(_hostingEnvironment).TrimEnd('/') + "/RenderMvc";
             // rewrite the path to the path of the handler (i.e. /umbraco/RenderMvc)
             context.RewritePath(rewritePath, "", query, false);