diff --git a/src/Umbraco.Abstractions/Configuration/IGlobalSettings.cs b/src/Umbraco.Abstractions/Configuration/IGlobalSettings.cs
index 25466d6cf7..212e6f1843 100644
--- a/src/Umbraco.Abstractions/Configuration/IGlobalSettings.cs
+++ b/src/Umbraco.Abstractions/Configuration/IGlobalSettings.cs
@@ -1,14 +1,5 @@
 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>
     /// Contains general settings information for the entire Umbraco instance based on information from  web.config appsettings
     /// </summary>
diff --git a/src/Umbraco.Abstractions/Configuration/IHostingSettings.cs b/src/Umbraco.Abstractions/Configuration/IHostingSettings.cs
new file mode 100644
index 0000000000..ef399177a4
--- /dev/null
+++ b/src/Umbraco.Abstractions/Configuration/IHostingSettings.cs
@@ -0,0 +1,11 @@
+namespace Umbraco.Core.Configuration
+{
+    public interface IHostingSettings
+    {
+        bool DebugMode { get; }
+        /// <summary>
+        /// Gets the configuration for the location of temporary files.
+        /// </summary>
+        LocalTempStorage LocalTempStorageLocation { get; }
+    }
+}
diff --git a/src/Umbraco.Abstractions/IO/IIOHelper.cs b/src/Umbraco.Abstractions/IO/IIOHelper.cs
index 2d535a8d1e..e8ef6d2973 100644
--- a/src/Umbraco.Abstractions/IO/IIOHelper.cs
+++ b/src/Umbraco.Abstractions/IO/IIOHelper.cs
@@ -11,7 +11,6 @@ namespace Umbraco.Core.IO
         string ResolveVirtualUrl(string path);
         string ResolveUrl(string virtualPath);
         Attempt<string> TryResolveUrl(string virtualPath);
-        string MapPath(string path, bool useHttpContext);
         string MapPath(string path);
 
 
diff --git a/src/Umbraco.Abstractions/IO/IOHelper.cs b/src/Umbraco.Abstractions/IO/IOHelper.cs
index 672228e3ca..d5e1335f35 100644
--- a/src/Umbraco.Abstractions/IO/IOHelper.cs
+++ b/src/Umbraco.Abstractions/IO/IOHelper.cs
@@ -5,6 +5,7 @@ using System.Reflection;
 using System.IO;
 using System.Linq;
 using Umbraco.Core.Hosting;
+using Umbraco.Core.Strings;
 
 namespace Umbraco.Core.IO
 {
@@ -78,10 +79,9 @@ namespace Umbraco.Core.IO
             }
         }
 
-        public string MapPath(string path, bool useHttpContext)
+        public string MapPath(string path)
         {
-            if (path == null) throw new ArgumentNullException("path");
-            useHttpContext = useHttpContext && _hostingEnvironment.IsHosted;
+            if (path == null) throw new ArgumentNullException(nameof(path));
 
             // Check if the path is already mapped
             if ((path.Length >= 2 && path[1] == Path.VolumeSeparatorChar)
@@ -93,7 +93,7 @@ namespace Umbraco.Core.IO
             // http://umbraco.codeplex.com/workitem/30946
 
 
-            if (useHttpContext && _hostingEnvironment.IsHosted)
+            if (_hostingEnvironment.IsHosted)
             {
                 var result = (String.IsNullOrEmpty(path) == false && (path.StartsWith("~") || path.StartsWith(Root)))
                         ?  _hostingEnvironment.MapPath(path)
@@ -113,10 +113,6 @@ namespace Umbraco.Core.IO
             return retval;
         }
 
-        public string MapPath(string path)
-        {
-            return MapPath(path, true);
-        }
 
         /// <summary>
         /// Verifies that the current filepath matches a directory where the user is allowed to edit a file.
@@ -276,7 +272,7 @@ namespace Umbraco.Core.IO
                 path = relativePath;
             }
 
-            return path.EnsurePathIsApplicationRootPrefixed();
+            return PathUtility.EnsurePathIsApplicationRootPrefixed(path);
         }
 
         private string _root;
diff --git a/src/Umbraco.Abstractions/StringExtensions.cs b/src/Umbraco.Abstractions/StringExtensions.cs
index 37a6ae4258..c838e3ec24 100644
--- a/src/Umbraco.Abstractions/StringExtensions.cs
+++ b/src/Umbraco.Abstractions/StringExtensions.cs
@@ -1215,21 +1215,6 @@ namespace Umbraco.Core
         public static string NullOrWhiteSpaceAsNull(this string text)
             => string.IsNullOrWhiteSpace(text) ? null : text;
 
-        /// <summary>
-        /// Ensures that a path has `~/` as prefix
-        /// </summary>
-        /// <param name="path"></param>
-        /// <returns></returns>
-        public static string EnsurePathIsApplicationRootPrefixed(this string path)
-        {
-            if (path.StartsWith("~/"))
-                return path;
-            if (path.StartsWith("/") == false && path.StartsWith("\\") == false)
-                path = string.Format("/{0}", path);
-            if (path.StartsWith("~") == false)
-                path = string.Format("~{0}", path);
-            return path;
-        }
 
         /// <summary>
         /// Checks if a given path is a full path including drive letter
diff --git a/src/Umbraco.Abstractions/Strings/PathUtility.cs b/src/Umbraco.Abstractions/Strings/PathUtility.cs
new file mode 100644
index 0000000000..973f1dccf2
--- /dev/null
+++ b/src/Umbraco.Abstractions/Strings/PathUtility.cs
@@ -0,0 +1,22 @@
+namespace Umbraco.Core.Strings
+{
+    public static class PathUtility
+    {
+
+        /// <summary>
+        /// Ensures that a path has `~/` as prefix
+        /// </summary>
+        /// <param name="path"></param>
+        /// <returns></returns>
+        public static string EnsurePathIsApplicationRootPrefixed(string path)
+        {
+            if (path.StartsWith("~/"))
+                return path;
+            if (path.StartsWith("/") == false && path.StartsWith("\\") == false)
+                path = string.Format("/{0}", path);
+            if (path.StartsWith("~") == false)
+                path = string.Format("~{0}", path);
+            return path;
+        }
+    }
+}
diff --git a/src/Umbraco.Configuration/GlobalSettings.cs b/src/Umbraco.Configuration/GlobalSettings.cs
index fea5de726f..ed7fdc2a91 100644
--- a/src/Umbraco.Configuration/GlobalSettings.cs
+++ b/src/Umbraco.Configuration/GlobalSettings.cs
@@ -8,6 +8,8 @@ namespace Umbraco.Core.Configuration
 {
     public class HostingSettings : IHostingSettings
     {
+        private bool? _debugMode;
+
         /// <inheritdoc />
         public LocalTempStorage LocalTempStorageLocation
         {
@@ -29,21 +31,25 @@ namespace Umbraco.Core.Configuration
         {
             get
             {
-                try
+                if (!_debugMode.HasValue)
                 {
-                    if (ConfigurationManager.GetSection("system.web/compilation") is ConfigurationSection compilation)
+                    try
                     {
-                        var debugElement = compilation.ElementInformation.Properties["debug"];
+                        if (ConfigurationManager.GetSection("system.web/compilation") is ConfigurationSection compilation)
+                        {
+                            var debugElement = compilation.ElementInformation.Properties["debug"];
 
-                        return debugElement != null && (debugElement.Value is bool debug && debug);
+                            _debugMode = debugElement != null && (debugElement.Value is bool debug && debug);
+
+                        }
+                    }
+                    catch
+                    {
+                        _debugMode = false;
                     }
                 }
-                catch
-                {
-                    // ignored
-                }
 
-                return false;
+                return _debugMode.GetValueOrDefault();
             }
         }
     }
diff --git a/src/Umbraco.Core/Logging/Serilog/Enrichers/HttpRequestIdEnricher.cs b/src/Umbraco.Core/Logging/Serilog/Enrichers/HttpRequestIdEnricher.cs
index f1dd04bf76..45468ace9f 100644
--- a/src/Umbraco.Core/Logging/Serilog/Enrichers/HttpRequestIdEnricher.cs
+++ b/src/Umbraco.Core/Logging/Serilog/Enrichers/HttpRequestIdEnricher.cs
@@ -13,11 +13,11 @@ namespace Umbraco.Core.Logging.Serilog.Enrichers
     /// </summary>
     internal class HttpRequestIdEnricher : ILogEventEnricher
     {
-        private readonly Func<IFactory> _factoryGetter;
+        private readonly Func<IRequestCache> _requestCacheGetter;
 
-        public HttpRequestIdEnricher(Func<IFactory> factoryGetter)
+        public HttpRequestIdEnricher(Func<IRequestCache> requestCacheGetter)
         {
-            _factoryGetter = factoryGetter;
+            _requestCacheGetter = requestCacheGetter;
         }
 
         /// <summary>
@@ -32,12 +32,10 @@ namespace Umbraco.Core.Logging.Serilog.Enrichers
         /// <param name="propertyFactory">Factory for creating new properties to add to the event.</param>
         public void Enrich(LogEvent logEvent, ILogEventPropertyFactory propertyFactory)
         {
-            if (logEvent == null) throw new ArgumentNullException("logEvent");
+            if (logEvent == null) throw new ArgumentNullException(nameof(logEvent));
 
-            var factory = _factoryGetter();
-            if(factory is null) return;
-
-            var requestCache = factory.GetInstance<IRequestCache>();
+            var requestCache = _requestCacheGetter();
+            if(requestCache is null) return;
 
             Guid requestId;
             if (!LogHttpRequest.TryGetCurrentHttpRequestId(out requestId, requestCache))
diff --git a/src/Umbraco.Core/Logging/Serilog/Enrichers/HttpRequestNumberEnricher.cs b/src/Umbraco.Core/Logging/Serilog/Enrichers/HttpRequestNumberEnricher.cs
index 5142f3d30f..08eb6b93f0 100644
--- a/src/Umbraco.Core/Logging/Serilog/Enrichers/HttpRequestNumberEnricher.cs
+++ b/src/Umbraco.Core/Logging/Serilog/Enrichers/HttpRequestNumberEnricher.cs
@@ -15,7 +15,7 @@ namespace Umbraco.Core.Logging.Serilog.Enrichers
     /// </summary>
     internal class HttpRequestNumberEnricher : ILogEventEnricher
     {
-        private readonly Func<IFactory> _factoryFunc;
+        private readonly Func<IRequestCache> _requestCacheGetter;
         private static int _lastRequestNumber;
         private static readonly string _requestNumberItemName = typeof(HttpRequestNumberEnricher).Name + "+RequestNumber";
 
@@ -25,9 +25,9 @@ namespace Umbraco.Core.Logging.Serilog.Enrichers
         private const string _httpRequestNumberPropertyName = "HttpRequestNumber";
 
 
-        public HttpRequestNumberEnricher(Func<IFactory> factoryFunc)
+        public HttpRequestNumberEnricher(Func<IRequestCache> requestCacheGetter)
         {
-            _factoryFunc = factoryFunc;
+            _requestCacheGetter = requestCacheGetter;
         }
 
         /// <summary>
@@ -39,10 +39,9 @@ namespace Umbraco.Core.Logging.Serilog.Enrichers
         {
             if (logEvent == null) throw new ArgumentNullException(nameof(logEvent));
 
-            var factory = _factoryFunc();
-            if (factory is null) return;
+            var requestCache = _requestCacheGetter();
+            if (requestCache is null) return;
 
-            var requestCache = factory.GetInstance<IRequestCache>();
             var requestNumber = requestCache.Get(_requestNumberItemName,
                     () => Interlocked.Increment(ref _lastRequestNumber));
 
diff --git a/src/Umbraco.Core/Logging/Serilog/LoggerConfigExtensions.cs b/src/Umbraco.Core/Logging/Serilog/LoggerConfigExtensions.cs
index 39b02d4684..f4e8f85281 100644
--- a/src/Umbraco.Core/Logging/Serilog/LoggerConfigExtensions.cs
+++ b/src/Umbraco.Core/Logging/Serilog/LoggerConfigExtensions.cs
@@ -25,7 +25,7 @@ namespace Umbraco.Core.Logging.Serilog
         /// </summary>
         /// <param name="logConfig">A Serilog LoggerConfiguration</param>
         /// <param name="hostingEnvironment"></param>
-        public static LoggerConfiguration MinimalConfiguration(this LoggerConfiguration logConfig, IHostingEnvironment hostingEnvironment, ISessionIdResolver sessionIdResolver, Func<IFactory> factoryFunc)
+        public static LoggerConfiguration MinimalConfiguration(this LoggerConfiguration logConfig, IHostingEnvironment hostingEnvironment, ISessionIdResolver sessionIdResolver, Func<IRequestCache> requestCacheGetter)
         {
             global::Serilog.Debugging.SelfLog.Enable(msg => System.Diagnostics.Debug.WriteLine(msg));
 
@@ -43,8 +43,8 @@ namespace Umbraco.Core.Logging.Serilog
                 .Enrich.WithProperty("MachineName", Environment.MachineName)
                 .Enrich.With<Log4NetLevelMapperEnricher>()
                 .Enrich.With(new HttpSessionIdEnricher(sessionIdResolver))
-                .Enrich.With(new HttpRequestNumberEnricher(factoryFunc))
-                .Enrich.With(new HttpRequestIdEnricher(factoryFunc));
+                .Enrich.With(new HttpRequestNumberEnricher(requestCacheGetter))
+                .Enrich.With(new HttpRequestIdEnricher(requestCacheGetter));
 
             return logConfig;
         }
diff --git a/src/Umbraco.Core/Logging/Serilog/SerilogLogger.cs b/src/Umbraco.Core/Logging/Serilog/SerilogLogger.cs
index 47623145ef..af5f712489 100644
--- a/src/Umbraco.Core/Logging/Serilog/SerilogLogger.cs
+++ b/src/Umbraco.Core/Logging/Serilog/SerilogLogger.cs
@@ -38,11 +38,11 @@ namespace Umbraco.Core.Logging.Serilog
         /// Creates a logger with some pre-defined configuration and remainder from config file
         /// </summary>
         /// <remarks>Used by UmbracoApplicationBase to get its logger.</remarks>
-        public static SerilogLogger CreateWithDefaultConfiguration(IHostingEnvironment hostingEnvironment, ISessionIdResolver sessionIdResolver, Func<IFactory> factoryFunc)
+        public static SerilogLogger CreateWithDefaultConfiguration(IHostingEnvironment hostingEnvironment, ISessionIdResolver sessionIdResolver, Func<IRequestCache> requestCacheGetter)
         {
             var loggerConfig = new LoggerConfiguration();
             loggerConfig
-                .MinimalConfiguration(hostingEnvironment, sessionIdResolver, factoryFunc)
+                .MinimalConfiguration(hostingEnvironment, sessionIdResolver, requestCacheGetter)
                 .ReadFromConfigFile()
                 .ReadFromUserConfigFile();
 
diff --git a/src/Umbraco.Tests/IO/IoHelperTests.cs b/src/Umbraco.Tests/IO/IoHelperTests.cs
index 910feb47be..9458f384ce 100644
--- a/src/Umbraco.Tests/IO/IoHelperTests.cs
+++ b/src/Umbraco.Tests/IO/IoHelperTests.cs
@@ -4,6 +4,7 @@ using Umbraco.Core.IO;
 using Umbraco.Core;
 using Umbraco.Core.Composing;
 using Umbraco.Core.Configuration;
+using Umbraco.Core.Strings;
 using Umbraco.Tests.TestHelpers;
 
 namespace Umbraco.Tests.IO
@@ -30,35 +31,13 @@ namespace Umbraco.Tests.IO
             }
         }
 
-        /// <summary>
-        ///A test for MapPath verifying that HttpContext method (which includes vdirs) matches non-HttpContext method
-        ///</summary>
-        [Test]
-        public void IOHelper_MapPathTestVDirTraversal()
-        {
-            //System.Diagnostics.Debugger.Break();
-            var globalSettings = SettingsForTests.GenerateMockGlobalSettings();
-
-            Assert.AreEqual(_ioHelper.MapPath(Constants.SystemDirectories.Bin, true), _ioHelper.MapPath(Constants.SystemDirectories.Bin, false));
-            Assert.AreEqual(_ioHelper.MapPath(Constants.SystemDirectories.Config, true), _ioHelper.MapPath(Constants.SystemDirectories.Config, false));
-            Assert.AreEqual(_ioHelper.MapPath(globalSettings.UmbracoCssPath, true), _ioHelper.MapPath(globalSettings.UmbracoCssPath, false));
-            Assert.AreEqual(_ioHelper.MapPath(Constants.SystemDirectories.Data, true), _ioHelper.MapPath(Constants.SystemDirectories.Data, false));
-            Assert.AreEqual(_ioHelper.MapPath(Constants.SystemDirectories.Install, true), _ioHelper.MapPath(Constants.SystemDirectories.Install, false));
-            Assert.AreEqual(_ioHelper.MapPath(globalSettings.UmbracoMediaPath, true), _ioHelper.MapPath(globalSettings.UmbracoMediaPath, false));
-            Assert.AreEqual(_ioHelper.MapPath(Constants.SystemDirectories.Packages, true), _ioHelper.MapPath(Constants.SystemDirectories.Packages, false));
-            Assert.AreEqual(_ioHelper.MapPath(Constants.SystemDirectories.Preview, true), _ioHelper.MapPath(Constants.SystemDirectories.Preview, false));
-            Assert.AreEqual(_ioHelper.MapPath(_ioHelper.Root, true), _ioHelper.MapPath(_ioHelper.Root, false));
-            Assert.AreEqual(_ioHelper.MapPath(globalSettings.UmbracoScriptsPath, true), _ioHelper.MapPath(globalSettings.UmbracoScriptsPath, false));
-            Assert.AreEqual(_ioHelper.MapPath(globalSettings.UmbracoPath, true), _ioHelper.MapPath(globalSettings.UmbracoPath, false));
-        }
-
         [Test]
         public void EnsurePathIsApplicationRootPrefixed()
         {
             //Assert
-            Assert.AreEqual("~/Views/Template.cshtml", "Views/Template.cshtml".EnsurePathIsApplicationRootPrefixed());
-            Assert.AreEqual("~/Views/Template.cshtml", "/Views/Template.cshtml".EnsurePathIsApplicationRootPrefixed());
-            Assert.AreEqual("~/Views/Template.cshtml", "~/Views/Template.cshtml".EnsurePathIsApplicationRootPrefixed());
+            Assert.AreEqual("~/Views/Template.cshtml", PathUtility.EnsurePathIsApplicationRootPrefixed("Views/Template.cshtml"));
+            Assert.AreEqual("~/Views/Template.cshtml", PathUtility.EnsurePathIsApplicationRootPrefixed("/Views/Template.cshtml"));
+            Assert.AreEqual("~/Views/Template.cshtml", PathUtility.EnsurePathIsApplicationRootPrefixed("~/Views/Template.cshtml"));
         }
     }
 }
diff --git a/src/Umbraco.Tests/Web/Controllers/AuthenticationControllerTests.cs b/src/Umbraco.Tests/Web/Controllers/AuthenticationControllerTests.cs
index 4d7815b991..e99d3eb165 100644
--- a/src/Umbraco.Tests/Web/Controllers/AuthenticationControllerTests.cs
+++ b/src/Umbraco.Tests/Web/Controllers/AuthenticationControllerTests.cs
@@ -71,7 +71,7 @@ namespace Umbraco.Tests.Web.Controllers
                 }
                 else
                 {
-                    var baseDir = IOHelper.MapPath("", false).TrimEnd(IOHelper.DirSepChar);
+                    var baseDir = IOHelper.MapPath("").TrimEnd(IOHelper.DirSepChar);
                     HttpContext.Current = new HttpContext(new SimpleWorkerRequest("/", baseDir, "", "", new StringWriter()));
                 }
                 IOHelper.ForceNotHosted = true;
diff --git a/src/Umbraco.Web/Mvc/UmbracoViewPageOfTModel.cs b/src/Umbraco.Web/Mvc/UmbracoViewPageOfTModel.cs
index 8e231de38d..c25a42195e 100644
--- a/src/Umbraco.Web/Mvc/UmbracoViewPageOfTModel.cs
+++ b/src/Umbraco.Web/Mvc/UmbracoViewPageOfTModel.cs
@@ -5,10 +5,6 @@ using System.Web.Mvc;
 using System.Web.WebPages;
 using Umbraco.Core;
 using Umbraco.Core.Cache;
-using Umbraco.Core.Composing;
-using Umbraco.Core.Configuration;
-using Umbraco.Core.Dictionary;
-using Umbraco.Core.IO;
 using Umbraco.Core.Models.PublishedContent;
 using Umbraco.Core.Services;
 using Umbraco.Core.Strings;
@@ -238,9 +234,9 @@ namespace Umbraco.Web.Mvc
 
         public override void Write(object value)
         {
-            if (value is IHtmlEncodedString)
+            if (value is IHtmlEncodedString htmlEncodedString)
             {
-                base.WriteLiteral(value);
+                base.WriteLiteral(htmlEncodedString.ToHtmlString());
             }
             else
             {
diff --git a/src/Umbraco.Web/UmbracoApplicationBase.cs b/src/Umbraco.Web/UmbracoApplicationBase.cs
index 313df4b619..b93e52088f 100644
--- a/src/Umbraco.Web/UmbracoApplicationBase.cs
+++ b/src/Umbraco.Web/UmbracoApplicationBase.cs
@@ -4,6 +4,7 @@ using System.Threading;
 using System.Web;
 using System.Web.Hosting;
 using Umbraco.Core;
+using Umbraco.Core.Cache;
 using Umbraco.Core.Composing;
 using Umbraco.Core.Configuration;
 using Umbraco.Core.Hosting;
@@ -45,7 +46,7 @@ namespace Umbraco.Web
 
             _profiler = new LogProfiler(_logger);
 
-            _logger = SerilogLogger.CreateWithDefaultConfiguration(_hostingEnvironment, new AspNetSessionIdResolver(), () => _factory);
+            _logger = SerilogLogger.CreateWithDefaultConfiguration(_hostingEnvironment, new AspNetSessionIdResolver(), () => _factory?.GetInstance<IRequestCache>());
             _backOfficeInfo = new AspNetBackOfficeInfo(_configs.Global(), _ioHelper, _configs.Settings(), _logger);
         }