diff --git a/src/Umbraco.Core/HealthChecks/Checks/Security/BaseHttpHeaderCheck.cs b/src/Umbraco.Core/HealthChecks/Checks/Security/BaseHttpHeaderCheck.cs
index 0f188bd390..0e7cbfe839 100644
--- a/src/Umbraco.Core/HealthChecks/Checks/Security/BaseHttpHeaderCheck.cs
+++ b/src/Umbraco.Core/HealthChecks/Checks/Security/BaseHttpHeaderCheck.cs
@@ -8,6 +8,7 @@ using System.Linq;
 using System.Net.Http;
 using System.Text.RegularExpressions;
 using System.Threading.Tasks;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.Services;
 using Umbraco.Web;
 
@@ -18,18 +19,18 @@ namespace Umbraco.Core.HealthChecks.Checks.Security
     /// </summary>
     public abstract class BaseHttpHeaderCheck : HealthCheck
     {
+        private readonly IHostingEnvironment _hostingEnvironment;
         private readonly string _header;
         private readonly string _value;
         private readonly string _localizedTextPrefix;
         private readonly bool _metaTagOptionAvailable;
-        private readonly IRequestAccessor _requestAccessor;
         private static HttpClient s_httpClient;
 
         /// <summary>
         /// Initializes a new instance of the <see cref="BaseHttpHeaderCheck"/> class.
         /// </summary>
         protected BaseHttpHeaderCheck(
-            IRequestAccessor requestAccessor,
+            IHostingEnvironment hostingEnvironment,
             ILocalizedTextService textService,
             string header,
             string value,
@@ -37,7 +38,7 @@ namespace Umbraco.Core.HealthChecks.Checks.Security
             bool metaTagOptionAvailable)
         {
             LocalizedTextService = textService ?? throw new ArgumentNullException(nameof(textService));
-            _requestAccessor = requestAccessor;
+            _hostingEnvironment = hostingEnvironment;
             _header = header;
             _value = value;
             _localizedTextPrefix = localizedTextPrefix;
@@ -78,7 +79,7 @@ namespace Umbraco.Core.HealthChecks.Checks.Security
             var success = false;
 
             // Access the site home page and check for the click-jack protection header or meta tag
-            Uri url = _requestAccessor.GetApplicationUrl();
+            Uri url = _hostingEnvironment.ApplicationMainUrl;
 
             try
             {
diff --git a/src/Umbraco.Core/HealthChecks/Checks/Security/ClickJackingCheck.cs b/src/Umbraco.Core/HealthChecks/Checks/Security/ClickJackingCheck.cs
index 9b654b5f8b..6bb92e4176 100644
--- a/src/Umbraco.Core/HealthChecks/Checks/Security/ClickJackingCheck.cs
+++ b/src/Umbraco.Core/HealthChecks/Checks/Security/ClickJackingCheck.cs
@@ -1,8 +1,8 @@
 // Copyright (c) Umbraco.
 // See LICENSE for more details.
 
+using Umbraco.Core.Hosting;
 using Umbraco.Core.Services;
-using Umbraco.Web;
 
 namespace Umbraco.Core.HealthChecks.Checks.Security
 {
@@ -19,8 +19,8 @@ namespace Umbraco.Core.HealthChecks.Checks.Security
         /// <summary>
         /// Initializes a new instance of the <see cref="ClickJackingCheck"/> class.
         /// </summary>
-        public ClickJackingCheck(IRequestAccessor requestAccessor, ILocalizedTextService textService)
-            : base(requestAccessor, textService, "X-Frame-Options", "sameorigin", "clickJacking", true)
+        public ClickJackingCheck(IHostingEnvironment hostingEnvironment, ILocalizedTextService textService)
+            : base(hostingEnvironment, textService, "X-Frame-Options", "sameorigin", "clickJacking", true)
         {
         }
 
diff --git a/src/Umbraco.Core/HealthChecks/Checks/Security/ExcessiveHeadersCheck.cs b/src/Umbraco.Core/HealthChecks/Checks/Security/ExcessiveHeadersCheck.cs
index 010683c6fe..000c14f93d 100644
--- a/src/Umbraco.Core/HealthChecks/Checks/Security/ExcessiveHeadersCheck.cs
+++ b/src/Umbraco.Core/HealthChecks/Checks/Security/ExcessiveHeadersCheck.cs
@@ -6,8 +6,8 @@ using System.Collections.Generic;
 using System.Linq;
 using System.Net.Http;
 using System.Threading.Tasks;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.Services;
-using Umbraco.Web;
 
 namespace Umbraco.Core.HealthChecks.Checks.Security
 {
@@ -22,16 +22,16 @@ namespace Umbraco.Core.HealthChecks.Checks.Security
     public class ExcessiveHeadersCheck : HealthCheck
     {
         private readonly ILocalizedTextService _textService;
-        private readonly IRequestAccessor _requestAccessor;
+        private readonly IHostingEnvironment _hostingEnvironment;
         private static HttpClient s_httpClient;
 
         /// <summary>
         /// Initializes a new instance of the <see cref="ExcessiveHeadersCheck"/> class.
         /// </summary>
-        public ExcessiveHeadersCheck(ILocalizedTextService textService, IRequestAccessor requestAccessor)
+        public ExcessiveHeadersCheck(ILocalizedTextService textService, IHostingEnvironment hostingEnvironment)
         {
             _textService = textService;
-            _requestAccessor = requestAccessor;
+            _hostingEnvironment = hostingEnvironment;
         }
 
         private static HttpClient HttpClient => s_httpClient ??= new HttpClient();
@@ -52,7 +52,7 @@ namespace Umbraco.Core.HealthChecks.Checks.Security
         {
             string message;
             var success = false;
-            Uri url = _requestAccessor.GetApplicationUrl();
+            Uri url = _hostingEnvironment.ApplicationMainUrl;
 
             // Access the site home page and check for the headers
             var request = new HttpRequestMessage(HttpMethod.Head, url);
diff --git a/src/Umbraco.Core/HealthChecks/Checks/Security/HstsCheck.cs b/src/Umbraco.Core/HealthChecks/Checks/Security/HstsCheck.cs
index 188e8f3080..828d2d2470 100644
--- a/src/Umbraco.Core/HealthChecks/Checks/Security/HstsCheck.cs
+++ b/src/Umbraco.Core/HealthChecks/Checks/Security/HstsCheck.cs
@@ -1,8 +1,8 @@
 // Copyright (c) Umbraco.
 // See LICENSE for more details.
 
+using Umbraco.Core.Hosting;
 using Umbraco.Core.Services;
-using Umbraco.Web;
 
 namespace Umbraco.Core.HealthChecks.Checks.Security
 {
@@ -26,8 +26,8 @@ namespace Umbraco.Core.HealthChecks.Checks.Security
         /// If you want do to it perfectly, you have to submit it https://hstspreload.org/,
         /// but then you should include subdomains and I wouldn't suggest to do that for Umbraco-sites.
         /// </remarks>
-        public HstsCheck(IRequestAccessor requestAccessor, ILocalizedTextService textService)
-            : base(requestAccessor, textService, "Strict-Transport-Security", "max-age=10886400", "hSTS", true)
+        public HstsCheck(IHostingEnvironment hostingEnvironment, ILocalizedTextService textService)
+            : base(hostingEnvironment, textService, "Strict-Transport-Security", "max-age=10886400", "hSTS", true)
         {
         }
 
diff --git a/src/Umbraco.Core/HealthChecks/Checks/Security/HttpsCheck.cs b/src/Umbraco.Core/HealthChecks/Checks/Security/HttpsCheck.cs
index 187fb2d300..5916c48b82 100644
--- a/src/Umbraco.Core/HealthChecks/Checks/Security/HttpsCheck.cs
+++ b/src/Umbraco.Core/HealthChecks/Checks/Security/HttpsCheck.cs
@@ -10,8 +10,8 @@ using System.Security.Cryptography.X509Certificates;
 using System.Threading.Tasks;
 using Microsoft.Extensions.Options;
 using Umbraco.Core.Configuration.Models;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.Services;
-using Umbraco.Web;
 
 namespace Umbraco.Core.HealthChecks.Checks.Security
 {
@@ -27,7 +27,7 @@ namespace Umbraco.Core.HealthChecks.Checks.Security
     {
         private readonly ILocalizedTextService _textService;
         private readonly IOptionsMonitor<GlobalSettings> _globalSettings;
-        private readonly IRequestAccessor _requestAccessor;
+        private readonly IHostingEnvironment _hostingEnvironment;
 
         private static HttpClient s_httpClient;
         private static HttpClientHandler s_httpClientHandler;
@@ -39,11 +39,11 @@ namespace Umbraco.Core.HealthChecks.Checks.Security
         public HttpsCheck(
             ILocalizedTextService textService,
             IOptionsMonitor<GlobalSettings> globalSettings,
-            IRequestAccessor requestAccessor)
+            IHostingEnvironment hostingEnvironment)
         {
             _textService = textService;
             _globalSettings = globalSettings;
-            _requestAccessor = requestAccessor;
+            _hostingEnvironment = hostingEnvironment;
         }
 
         private static HttpClient HttpClient => s_httpClient ??= new HttpClient(HttpClientHandler);
@@ -85,7 +85,7 @@ namespace Umbraco.Core.HealthChecks.Checks.Security
 
             // Attempt to access the site over HTTPS to see if it HTTPS is supported
             // and a valid certificate has been configured
-            var url = _requestAccessor.GetApplicationUrl().ToString().Replace("http:", "https:");
+            var url = _hostingEnvironment.ApplicationMainUrl.ToString().Replace("http:", "https:");
 
             var request = new HttpRequestMessage(HttpMethod.Head, url);
 
@@ -148,7 +148,7 @@ namespace Umbraco.Core.HealthChecks.Checks.Security
 
         private Task<HealthCheckStatus> CheckIfCurrentSchemeIsHttps()
         {
-            Uri uri = _requestAccessor.GetApplicationUrl();
+            Uri uri = _hostingEnvironment.ApplicationMainUrl;
             var success = uri.Scheme == "https";
 
             return Task.FromResult(new HealthCheckStatus(_textService.Localize("healthcheck/httpsCheckIsCurrentSchemeHttps", new[] { success ? string.Empty : "not" }))
@@ -161,7 +161,7 @@ namespace Umbraco.Core.HealthChecks.Checks.Security
         private Task<HealthCheckStatus> CheckHttpsConfigurationSetting()
         {
             bool httpsSettingEnabled = _globalSettings.CurrentValue.UseHttps;
-            Uri uri = _requestAccessor.GetApplicationUrl();
+            Uri uri = _hostingEnvironment.ApplicationMainUrl;
 
             string resultMessage;
             StatusResultType resultType;
diff --git a/src/Umbraco.Core/HealthChecks/Checks/Security/NoSniffCheck.cs b/src/Umbraco.Core/HealthChecks/Checks/Security/NoSniffCheck.cs
index b74be4ca6b..0722f4cf64 100644
--- a/src/Umbraco.Core/HealthChecks/Checks/Security/NoSniffCheck.cs
+++ b/src/Umbraco.Core/HealthChecks/Checks/Security/NoSniffCheck.cs
@@ -1,8 +1,8 @@
 // Copyright (c) Umbraco.
 // See LICENSE for more details.
 
+using Umbraco.Core.Hosting;
 using Umbraco.Core.Services;
-using Umbraco.Web;
 
 namespace Umbraco.Core.HealthChecks.Checks.Security
 {
@@ -19,8 +19,8 @@ namespace Umbraco.Core.HealthChecks.Checks.Security
         /// <summary>
         /// Initializes a new instance of the <see cref="NoSniffCheck"/> class.
         /// </summary>
-        public NoSniffCheck(IRequestAccessor requestAccessor, ILocalizedTextService textService)
-            : base(requestAccessor, textService, "X-Content-Type-Options", "nosniff", "noSniff", false)
+        public NoSniffCheck(IHostingEnvironment hostingEnvironment, ILocalizedTextService textService)
+            : base(hostingEnvironment, textService, "X-Content-Type-Options", "nosniff", "noSniff", false)
         {
         }
 
diff --git a/src/Umbraco.Core/HealthChecks/Checks/Security/XssProtectionCheck.cs b/src/Umbraco.Core/HealthChecks/Checks/Security/XssProtectionCheck.cs
index 29d14ee238..5a1973d05b 100644
--- a/src/Umbraco.Core/HealthChecks/Checks/Security/XssProtectionCheck.cs
+++ b/src/Umbraco.Core/HealthChecks/Checks/Security/XssProtectionCheck.cs
@@ -1,8 +1,8 @@
 // Copyright (c) Umbraco.
 // See LICENSE for more details.
 
+using Umbraco.Core.Hosting;
 using Umbraco.Core.Services;
-using Umbraco.Web;
 
 namespace Umbraco.Core.HealthChecks.Checks.Security
 {
@@ -26,8 +26,8 @@ namespace Umbraco.Core.HealthChecks.Checks.Security
         /// If you want do to it perfectly, you have to submit it https://hstspreload.appspot.com/,
         /// but then you should include subdomains and I wouldn't suggest to do that for Umbraco-sites.
         /// </remarks>
-        public XssProtectionCheck(IRequestAccessor requestAccessor, ILocalizedTextService textService)
-            : base(requestAccessor, textService, "X-XSS-Protection", "1; mode=block", "xssProtection", true)
+        public XssProtectionCheck(IHostingEnvironment hostingEnvironment, ILocalizedTextService textService)
+            : base(hostingEnvironment, textService, "X-XSS-Protection", "1; mode=block", "xssProtection", true)
         {
         }
 
diff --git a/src/Umbraco.Core/HealthChecks/NotificationMethods/EmailNotificationMethod.cs b/src/Umbraco.Core/HealthChecks/NotificationMethods/EmailNotificationMethod.cs
index 7492b8b9ad..97ef86d205 100644
--- a/src/Umbraco.Core/HealthChecks/NotificationMethods/EmailNotificationMethod.cs
+++ b/src/Umbraco.Core/HealthChecks/NotificationMethods/EmailNotificationMethod.cs
@@ -2,10 +2,10 @@
 using System.Threading.Tasks;
 using Microsoft.Extensions.Options;
 using Umbraco.Core.Configuration.Models;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.Mail;
 using Umbraco.Core.Models;
 using Umbraco.Core.Services;
-using Umbraco.Web;
 
 namespace Umbraco.Core.HealthChecks.NotificationMethods
 {
@@ -13,7 +13,7 @@ namespace Umbraco.Core.HealthChecks.NotificationMethods
     public class EmailNotificationMethod : NotificationMethodBase
     {
         private readonly ILocalizedTextService _textService;
-        private readonly IRequestAccessor _requestAccessor;
+        private readonly IHostingEnvironment _hostingEnvironment;
         private readonly IEmailSender _emailSender;
         private readonly IMarkdownToHtmlConverter _markdownToHtmlConverter;
 
@@ -21,7 +21,7 @@ namespace Umbraco.Core.HealthChecks.NotificationMethods
 
         public EmailNotificationMethod(
             ILocalizedTextService textService,
-            IRequestAccessor requestAccessor,
+            IHostingEnvironment hostingEnvironment,
             IEmailSender emailSender,
             IOptions<HealthChecksSettings> healthChecksSettings,
             IOptions<ContentSettings> contentSettings,
@@ -38,7 +38,7 @@ namespace Umbraco.Core.HealthChecks.NotificationMethods
             RecipientEmail = recipientEmail;
 
             _textService = textService ?? throw new ArgumentNullException(nameof(textService));
-            _requestAccessor = requestAccessor;
+            _hostingEnvironment = hostingEnvironment;
             _emailSender = emailSender;
             _markdownToHtmlConverter = markdownToHtmlConverter;
             _contentSettings = contentSettings.Value ?? throw new ArgumentNullException(nameof(contentSettings));
@@ -67,9 +67,9 @@ namespace Umbraco.Core.HealthChecks.NotificationMethods
 
             // Include the umbraco Application URL host in the message subject so that
             // you can identify the site that these results are for.
-            var host = _requestAccessor.GetApplicationUrl();
+            var host = _hostingEnvironment.ApplicationMainUrl?.ToString();
 
-            var subject = _textService.Localize("healthcheck/scheduledHealthCheckEmailSubject", new[] { host.ToString() });
+            var subject = _textService.Localize("healthcheck/scheduledHealthCheckEmailSubject", new[] { host });
 
 
             var mailMessage = CreateMailMessage(subject, message);
diff --git a/src/Umbraco.Core/Hosting/IHostingEnvironment.cs b/src/Umbraco.Core/Hosting/IHostingEnvironment.cs
index ff2b3adfa5..e01435422d 100644
--- a/src/Umbraco.Core/Hosting/IHostingEnvironment.cs
+++ b/src/Umbraco.Core/Hosting/IHostingEnvironment.cs
@@ -31,6 +31,11 @@ namespace Umbraco.Core.Hosting
         /// </summary>
         bool IsHosted { get; }
 
+        /// <summary>
+        /// Gets the main application url.
+        /// </summary>
+        Uri ApplicationMainUrl { get; }
+
         /// <summary>
         /// Maps a virtual path to a physical path to the application's web root
         /// </summary>
@@ -61,5 +66,10 @@ namespace Umbraco.Core.Hosting
         /// If virtualPath does not start with ~/ or /
         /// </exception>
         string ToAbsolute(string virtualPath);
+
+        /// <summary>
+        /// Ensures that the application know its main Url.
+        /// </summary>
+        void EnsureApplicationMainUrl(Uri currentApplicationUrl);
     }
 }
diff --git a/src/Umbraco.Core/Web/IRequestAccessor.cs b/src/Umbraco.Core/Web/IRequestAccessor.cs
index 275c96bf23..56c8091f94 100644
--- a/src/Umbraco.Core/Web/IRequestAccessor.cs
+++ b/src/Umbraco.Core/Web/IRequestAccessor.cs
@@ -1,5 +1,4 @@
 using System;
-using Umbraco.Web.Routing;
 
 namespace Umbraco.Web
 {
@@ -19,8 +18,5 @@ namespace Umbraco.Web
         /// Returns the current request uri
         /// </summary>
         Uri GetRequestUrl();
-
-        // TODO: This doesn't belongs here
-        Uri GetApplicationUrl();
     }
 }
diff --git a/src/Umbraco.Infrastructure/Compose/NotificationsComponent.cs b/src/Umbraco.Infrastructure/Compose/NotificationsComponent.cs
index 767f36aaf5..ad3efc88df 100644
--- a/src/Umbraco.Infrastructure/Compose/NotificationsComponent.cs
+++ b/src/Umbraco.Infrastructure/Compose/NotificationsComponent.cs
@@ -2,11 +2,12 @@
 using System.Collections.Generic;
 using System.Globalization;
 using System.Linq;
-using Microsoft.Extensions.Options;
 using Microsoft.Extensions.Logging;
+using Microsoft.Extensions.Options;
 using Umbraco.Core;
 using Umbraco.Core.Composing;
 using Umbraco.Core.Configuration.Models;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.Models;
 using Umbraco.Core.Models.Entities;
 using Umbraco.Core.Models.Membership;
@@ -185,7 +186,7 @@ namespace Umbraco.Web.Compose
         public sealed class Notifier
         {
             private readonly IBackOfficeSecurityAccessor _backOfficeSecurityAccessor;
-            private readonly IRequestAccessor _requestAccessor;
+            private readonly IHostingEnvironment _hostingEnvironment;
             private readonly INotificationService _notificationService;
             private readonly IUserService _userService;
             private readonly ILocalizedTextService _textService;
@@ -193,18 +194,11 @@ namespace Umbraco.Web.Compose
             private readonly ILogger<Notifier> _logger;
 
             /// <summary>
-            /// Constructor
+            /// Initializes a new instance of the <see cref="Notifier"/> class.
             /// </summary>
-            /// <param name="backOfficeSecurityAccessor"></param>
-            /// <param name="requestAccessor"></param>
-            /// <param name="notificationService"></param>
-            /// <param name="userService"></param>
-            /// <param name="textService"></param>
-            /// <param name="globalSettings"></param>
-            /// <param name="logger"></param>
             public Notifier(
                 IBackOfficeSecurityAccessor backOfficeSecurityAccessor,
-                IRequestAccessor requestAccessor,
+                IHostingEnvironment hostingEnvironment,
                 INotificationService notificationService,
                 IUserService userService,
                 ILocalizedTextService textService,
@@ -212,7 +206,7 @@ namespace Umbraco.Web.Compose
                 ILogger<Notifier> logger)
             {
                 _backOfficeSecurityAccessor = backOfficeSecurityAccessor;
-                _requestAccessor = requestAccessor;
+                _hostingEnvironment = hostingEnvironment;
                 _notificationService = notificationService;
                 _userService = userService;
                 _textService = textService;
@@ -236,7 +230,7 @@ namespace Umbraco.Web.Compose
                     }
                 }
 
-                SendNotification(user, entities, action, _requestAccessor.GetApplicationUrl());
+                SendNotification(user, entities, action, _hostingEnvironment.ApplicationMainUrl);
             }
 
             private void SendNotification(IUser sender, IEnumerable<IContent> entities, IAction action, Uri siteUri)
diff --git a/src/Umbraco.Infrastructure/HostedServices/KeepAlive.cs b/src/Umbraco.Infrastructure/HostedServices/KeepAlive.cs
index 0ec237c6d6..a020f04b16 100644
--- a/src/Umbraco.Infrastructure/HostedServices/KeepAlive.cs
+++ b/src/Umbraco.Infrastructure/HostedServices/KeepAlive.cs
@@ -8,6 +8,7 @@ using Microsoft.Extensions.Logging;
 using Microsoft.Extensions.Options;
 using Umbraco.Core;
 using Umbraco.Core.Configuration.Models;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.Logging;
 using Umbraco.Core.Sync;
 using Umbraco.Web;
@@ -19,7 +20,7 @@ namespace Umbraco.Infrastructure.HostedServices
     /// </summary>
     public class KeepAlive : RecurringHostedServiceBase
     {
-        private readonly IRequestAccessor _requestAccessor;
+        private readonly IHostingEnvironment _hostingEnvironment;
         private readonly IMainDom _mainDom;
         private readonly KeepAliveSettings _keepAliveSettings;
         private readonly ILogger<KeepAlive> _logger;
@@ -38,7 +39,7 @@ namespace Umbraco.Infrastructure.HostedServices
         /// <param name="serverRegistrar">Provider of server registrations to the distributed cache.</param>
         /// <param name="httpClientFactory">Factory for <see cref="HttpClient" /> instances.</param>
         public KeepAlive(
-            IRequestAccessor requestAccessor,
+            IHostingEnvironment hostingEnvironment,
             IMainDom mainDom,
             IOptions<KeepAliveSettings> keepAliveSettings,
             ILogger<KeepAlive> logger,
@@ -47,7 +48,7 @@ namespace Umbraco.Infrastructure.HostedServices
             IHttpClientFactory httpClientFactory)
             : base(TimeSpan.FromMinutes(5), DefaultDelay)
         {
-            _requestAccessor = requestAccessor;
+            _hostingEnvironment = hostingEnvironment;
             _mainDom = mainDom;
             _keepAliveSettings = keepAliveSettings.Value;
             _logger = logger;
@@ -88,7 +89,7 @@ namespace Umbraco.Infrastructure.HostedServices
                 {
                     if (keepAlivePingUrl.Contains("{umbracoApplicationUrl}"))
                     {
-                        var umbracoAppUrl = _requestAccessor.GetApplicationUrl().ToString();
+                        var umbracoAppUrl = _hostingEnvironment.ApplicationMainUrl.ToString();
                         if (umbracoAppUrl.IsNullOrWhiteSpace())
                         {
                             _logger.LogWarning("No umbracoApplicationUrl for service (yet), skip.");
diff --git a/src/Umbraco.Infrastructure/HostedServices/ServerRegistration/TouchServerTask.cs b/src/Umbraco.Infrastructure/HostedServices/ServerRegistration/TouchServerTask.cs
index 69f9280fc0..6771705c8e 100644
--- a/src/Umbraco.Infrastructure/HostedServices/ServerRegistration/TouchServerTask.cs
+++ b/src/Umbraco.Infrastructure/HostedServices/ServerRegistration/TouchServerTask.cs
@@ -7,8 +7,8 @@ using Microsoft.Extensions.Logging;
 using Microsoft.Extensions.Options;
 using Umbraco.Core;
 using Umbraco.Core.Configuration.Models;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.Services;
-using Umbraco.Web;
 
 namespace Umbraco.Infrastructure.HostedServices.ServerRegistration
 {
@@ -19,7 +19,7 @@ namespace Umbraco.Infrastructure.HostedServices.ServerRegistration
     {
         private readonly IRuntimeState _runtimeState;
         private readonly IServerRegistrationService _serverRegistrationService;
-        private readonly IRequestAccessor _requestAccessor;
+        private readonly IHostingEnvironment _hostingEnvironment;
         private readonly ILogger<TouchServerTask> _logger;
         private readonly GlobalSettings _globalSettings;
 
@@ -31,12 +31,17 @@ namespace Umbraco.Infrastructure.HostedServices.ServerRegistration
         /// <param name="requestAccessor">Accessor for the current request.</param>
         /// <param name="logger">The typed logger.</param>
         /// <param name="globalSettings">The configuration for global settings.</param>
-        public TouchServerTask(IRuntimeState runtimeState, IServerRegistrationService serverRegistrationService, IRequestAccessor requestAccessor, ILogger<TouchServerTask> logger, IOptions<GlobalSettings> globalSettings)
+        public TouchServerTask(
+            IRuntimeState runtimeState,
+            IServerRegistrationService serverRegistrationService,
+            IHostingEnvironment hostingEnvironment,
+            ILogger<TouchServerTask> logger,
+            IOptions<GlobalSettings> globalSettings)
             : base(globalSettings.Value.DatabaseServerRegistrar.WaitTimeBetweenCalls, TimeSpan.FromSeconds(15))
         {
             _runtimeState = runtimeState;
             _serverRegistrationService = serverRegistrationService ?? throw new ArgumentNullException(nameof(serverRegistrationService));
-            _requestAccessor = requestAccessor;
+            _hostingEnvironment = hostingEnvironment;
             _logger = logger;
             _globalSettings = globalSettings.Value;
         }
@@ -48,7 +53,7 @@ namespace Umbraco.Infrastructure.HostedServices.ServerRegistration
                 return Task.CompletedTask;
             }
 
-            var serverAddress = _requestAccessor.GetApplicationUrl()?.ToString();
+            var serverAddress = _hostingEnvironment.ApplicationMainUrl?.ToString();
             if (serverAddress.IsNullOrWhiteSpace())
             {
                 _logger.LogWarning("No umbracoApplicationUrl for service (yet), skip.");
diff --git a/src/Umbraco.Tests.Integration/Implementations/TestHelper.cs b/src/Umbraco.Tests.Integration/Implementations/TestHelper.cs
index 4c698b221d..8bdca33561 100644
--- a/src/Umbraco.Tests.Integration/Implementations/TestHelper.cs
+++ b/src/Umbraco.Tests.Integration/Implementations/TestHelper.cs
@@ -141,6 +141,7 @@ namespace Umbraco.Tests.Integration.Implementations
         public override IHostingEnvironment GetHostingEnvironment()
             => _hostingEnvironment ??= new TestHostingEnvironment(
                 GetIOptionsMonitorOfHostingSettings(),
+                GetIOptionsMonitorOfWebRoutingSettings(),
                 _hostEnvironment);
 
         private IOptionsMonitor<HostingSettings> GetIOptionsMonitorOfHostingSettings()
@@ -149,6 +150,12 @@ namespace Umbraco.Tests.Integration.Implementations
             return Mock.Of<IOptionsMonitor<HostingSettings>>(x => x.CurrentValue == hostingSettings);
         }
 
+        private IOptionsMonitor<WebRoutingSettings> GetIOptionsMonitorOfWebRoutingSettings()
+        {
+            var webRoutingSettings = new WebRoutingSettings();
+            return Mock.Of<IOptionsMonitor<WebRoutingSettings>>(x => x.CurrentValue == webRoutingSettings);
+        }
+
         public override IApplicationShutdownRegistry GetHostingEnvironmentLifetime() => _hostingLifetime;
 
         public override IIpResolver GetIpResolver() => _ipResolver;
diff --git a/src/Umbraco.Tests.Integration/Implementations/TestHostingEnvironment.cs b/src/Umbraco.Tests.Integration/Implementations/TestHostingEnvironment.cs
index 2a91b6db83..8690a5f6f8 100644
--- a/src/Umbraco.Tests.Integration/Implementations/TestHostingEnvironment.cs
+++ b/src/Umbraco.Tests.Integration/Implementations/TestHostingEnvironment.cs
@@ -11,8 +11,8 @@ namespace Umbraco.Tests.Integration.Implementations
 {
     public class TestHostingEnvironment : AspNetCoreHostingEnvironment, IHostingEnvironment
     {
-        public TestHostingEnvironment(IOptionsMonitor<HostingSettings> hostingSettings, IWebHostEnvironment webHostEnvironment)
-            : base(hostingSettings, webHostEnvironment)
+        public TestHostingEnvironment(IOptionsMonitor<HostingSettings> hostingSettings,IOptionsMonitor<WebRoutingSettings> webRoutingSettings, IWebHostEnvironment webHostEnvironment)
+            : base(hostingSettings,webRoutingSettings, webHostEnvironment)
         {
         }
 
diff --git a/src/Umbraco.Tests.UnitTests/TestHelpers/TestHelper.cs b/src/Umbraco.Tests.UnitTests/TestHelpers/TestHelper.cs
index b23ccc9080..9da0f84202 100644
--- a/src/Umbraco.Tests.UnitTests/TestHelpers/TestHelper.cs
+++ b/src/Umbraco.Tests.UnitTests/TestHelpers/TestHelper.cs
@@ -71,6 +71,7 @@ namespace Umbraco.Tests.TestHelpers
                 var testPath = TestContext.CurrentContext.TestDirectory.Split("bin")[0];
                 return new AspNetCoreHostingEnvironment(
                     Mock.Of<IOptionsMonitor<HostingSettings>>(x => x.CurrentValue == new HostingSettings()),
+                    Mock.Of<IOptionsMonitor<WebRoutingSettings>>(x => x.CurrentValue == new WebRoutingSettings()),
                     Mock.Of<IWebHostEnvironment>(
                         x =>
                             x.WebRootPath == "/" &&
diff --git a/src/Umbraco.Tests.UnitTests/Umbraco.Core/Extensions/UriExtensionsTests.cs b/src/Umbraco.Tests.UnitTests/Umbraco.Core/Extensions/UriExtensionsTests.cs
index fc8ecd0474..fa5ff0df0b 100644
--- a/src/Umbraco.Tests.UnitTests/Umbraco.Core/Extensions/UriExtensionsTests.cs
+++ b/src/Umbraco.Tests.UnitTests/Umbraco.Core/Extensions/UriExtensionsTests.cs
@@ -28,8 +28,10 @@ namespace Umbraco.Tests.UnitTests.Umbraco.Core.Extensions
         private AspNetCoreHostingEnvironment CreateHostingEnvironment(string virtualPath = "")
         {
             var hostingSettings = new HostingSettings { ApplicationVirtualPath = virtualPath };
+            var webRoutingSettings = new WebRoutingSettings();
             var mockedOptionsMonitorOfHostingSettings = Mock.Of<IOptionsMonitor<HostingSettings>>(x => x.CurrentValue == hostingSettings);
-            return new AspNetCoreHostingEnvironment(mockedOptionsMonitorOfHostingSettings, _hostEnvironment);
+            var mockedOptionsMonitorOfWebRoutingSettings = Mock.Of<IOptionsMonitor<WebRoutingSettings>>(x => x.CurrentValue == webRoutingSettings);
+            return new AspNetCoreHostingEnvironment(mockedOptionsMonitorOfHostingSettings, mockedOptionsMonitorOfWebRoutingSettings, _hostEnvironment);
         }
 
         [TestCase("http://www.domain.com/foo/bar", "/", "http://www.domain.com/")]
diff --git a/src/Umbraco.Tests.UnitTests/Umbraco.Core/Routing/UmbracoRequestPathsTests.cs b/src/Umbraco.Tests.UnitTests/Umbraco.Core/Routing/UmbracoRequestPathsTests.cs
index 24f0b04080..57015f30ea 100644
--- a/src/Umbraco.Tests.UnitTests/Umbraco.Core/Routing/UmbracoRequestPathsTests.cs
+++ b/src/Umbraco.Tests.UnitTests/Umbraco.Core/Routing/UmbracoRequestPathsTests.cs
@@ -25,9 +25,12 @@ namespace Umbraco.Tests.UnitTests.Umbraco.Core.Routing
 
         private AspNetCoreHostingEnvironment CreateHostingEnvironment(string virtualPath = "")
         {
+
             var hostingSettings = new HostingSettings { ApplicationVirtualPath = virtualPath };
+            var webRoutingSettings = new WebRoutingSettings();
             var mockedOptionsMonitorOfHostingSettings = Mock.Of<IOptionsMonitor<HostingSettings>>(x => x.CurrentValue == hostingSettings);
-            return new AspNetCoreHostingEnvironment(mockedOptionsMonitorOfHostingSettings, _hostEnvironment);
+            var mockedOptionsMonitorOfWebRoutingSettings = Mock.Of<IOptionsMonitor<WebRoutingSettings>>(x => x.CurrentValue == webRoutingSettings);
+            return new AspNetCoreHostingEnvironment(mockedOptionsMonitorOfHostingSettings, mockedOptionsMonitorOfWebRoutingSettings, _hostEnvironment);
         }
 
         [TestCase("/favicon.ico", true)]
@@ -65,7 +68,7 @@ namespace Umbraco.Tests.UnitTests.Umbraco.Core.Routing
         [TestCase("http://www.domain.com/Umbraco/", "", true)]
         [TestCase("http://www.domain.com/umbraco/default.aspx", "", true)]
         [TestCase("http://www.domain.com/umbraco/test/test", "", false)]
-        [TestCase("http://www.domain.com/umbraco/test/test/test", "", false)]        
+        [TestCase("http://www.domain.com/umbraco/test/test/test", "", false)]
         [TestCase("http://www.domain.com/umbrac", "", false)]
         [TestCase("http://www.domain.com/test", "", false)]
         [TestCase("http://www.domain.com/test/umbraco", "", false)]
@@ -84,7 +87,7 @@ namespace Umbraco.Tests.UnitTests.Umbraco.Core.Routing
             var umbracoRequestPaths = new UmbracoRequestPaths(Options.Create(_globalSettings), hostingEnvironment);
             Assert.AreEqual(expected, umbracoRequestPaths.IsBackOfficeRequest(source.AbsolutePath));
         }
-        
+
         [TestCase("http://www.domain.com/install", true)]
         [TestCase("http://www.domain.com/Install/", true)]
         [TestCase("http://www.domain.com/install/default.aspx", true)]
diff --git a/src/Umbraco.Tests.UnitTests/Umbraco.Infrastructure/HostedServices/KeepAliveTests.cs b/src/Umbraco.Tests.UnitTests/Umbraco.Infrastructure/HostedServices/KeepAliveTests.cs
index 752da01f0f..67c83e0642 100644
--- a/src/Umbraco.Tests.UnitTests/Umbraco.Infrastructure/HostedServices/KeepAliveTests.cs
+++ b/src/Umbraco.Tests.UnitTests/Umbraco.Infrastructure/HostedServices/KeepAliveTests.cs
@@ -13,6 +13,7 @@ using Moq.Protected;
 using NUnit.Framework;
 using Umbraco.Core;
 using Umbraco.Core.Configuration.Models;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.Logging;
 using Umbraco.Core.Scoping;
 using Umbraco.Core.Sync;
@@ -78,8 +79,8 @@ namespace Umbraco.Tests.UnitTests.Umbraco.Infrastructure.HostedServices
                 DisableKeepAliveTask = !enabled,
             };
 
-            var mockRequestAccessor = new Mock<IRequestAccessor>();
-            mockRequestAccessor.Setup(x => x.GetApplicationUrl()).Returns(new Uri(ApplicationUrl));
+            var mockRequestAccessor = new Mock<IHostingEnvironment>();
+            mockRequestAccessor.SetupGet(x => x.ApplicationMainUrl).Returns(new Uri(ApplicationUrl));
 
             var mockServerRegistrar = new Mock<IServerRoleAccessor>();
             mockServerRegistrar.Setup(x => x.CurrentServerRole).Returns(serverRole);
diff --git a/src/Umbraco.Tests.UnitTests/Umbraco.Infrastructure/HostedServices/ServerRegistration/TouchServerTaskTests.cs b/src/Umbraco.Tests.UnitTests/Umbraco.Infrastructure/HostedServices/ServerRegistration/TouchServerTaskTests.cs
index d293a5b7e8..5b97c36d16 100644
--- a/src/Umbraco.Tests.UnitTests/Umbraco.Infrastructure/HostedServices/ServerRegistration/TouchServerTaskTests.cs
+++ b/src/Umbraco.Tests.UnitTests/Umbraco.Infrastructure/HostedServices/ServerRegistration/TouchServerTaskTests.cs
@@ -9,9 +9,9 @@ using Moq;
 using NUnit.Framework;
 using Umbraco.Core;
 using Umbraco.Core.Configuration.Models;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.Services;
 using Umbraco.Infrastructure.HostedServices.ServerRegistration;
-using Umbraco.Web;
 
 namespace Umbraco.Tests.UnitTests.Umbraco.Infrastructure.HostedServices.ServerRegistration
 {
@@ -53,8 +53,8 @@ namespace Umbraco.Tests.UnitTests.Umbraco.Infrastructure.HostedServices.ServerRe
 
         private TouchServerTask CreateTouchServerTask(RuntimeLevel runtimeLevel = RuntimeLevel.Run, string applicationUrl = ApplicationUrl)
         {
-            var mockRequestAccessor = new Mock<IRequestAccessor>();
-            mockRequestAccessor.Setup(x => x.GetApplicationUrl()).Returns(!string.IsNullOrEmpty(applicationUrl) ? new Uri(ApplicationUrl) : null);
+            var mockRequestAccessor = new Mock<IHostingEnvironment>();
+            mockRequestAccessor.SetupGet(x => x.ApplicationMainUrl).Returns(!string.IsNullOrEmpty(applicationUrl) ? new Uri(ApplicationUrl) : null);
 
             var mockRunTimeState = new Mock<IRuntimeState>();
             mockRunTimeState.SetupGet(x => x.Level).Returns(runtimeLevel);
@@ -62,7 +62,7 @@ namespace Umbraco.Tests.UnitTests.Umbraco.Infrastructure.HostedServices.ServerRe
             var mockLogger = new Mock<ILogger<TouchServerTask>>();
 
             _mockServerRegistrationService = new Mock<IServerRegistrationService>();
-            
+
             var settings = new GlobalSettings
             {
                 DatabaseServerRegistrar = new DatabaseServerRegistrarSettings
diff --git a/src/Umbraco.Web.BackOffice/Controllers/AuthenticationController.cs b/src/Umbraco.Web.BackOffice/Controllers/AuthenticationController.cs
index 11931b5f47..5e512b2342 100644
--- a/src/Umbraco.Web.BackOffice/Controllers/AuthenticationController.cs
+++ b/src/Umbraco.Web.BackOffice/Controllers/AuthenticationController.cs
@@ -64,7 +64,6 @@ namespace Umbraco.Web.BackOffice.Controllers
         private readonly IEmailSender _emailSender;
         private readonly ISmsSender _smsSender;
         private readonly Core.Hosting.IHostingEnvironment _hostingEnvironment;
-        private readonly IRequestAccessor _requestAccessor;
         private readonly LinkGenerator _linkGenerator;
         private readonly IBackOfficeExternalLoginProviders _externalAuthenticationOptions;
         private readonly IBackOfficeTwoFactorOptions _backOfficeTwoFactorOptions;
@@ -86,7 +85,6 @@ namespace Umbraco.Web.BackOffice.Controllers
             IEmailSender emailSender,
             ISmsSender smsSender,
             Core.Hosting.IHostingEnvironment hostingEnvironment,
-            IRequestAccessor requestAccessor,
             LinkGenerator linkGenerator,
             IBackOfficeExternalLoginProviders externalAuthenticationOptions,
             IBackOfficeTwoFactorOptions backOfficeTwoFactorOptions)
@@ -105,7 +103,6 @@ namespace Umbraco.Web.BackOffice.Controllers
             _emailSender = emailSender;
             _smsSender = smsSender;
             _hostingEnvironment = hostingEnvironment;
-            _requestAccessor = requestAccessor;
             _linkGenerator = linkGenerator;
             _externalAuthenticationOptions = externalAuthenticationOptions;
             _backOfficeTwoFactorOptions = backOfficeTwoFactorOptions;
@@ -624,7 +621,7 @@ namespace Umbraco.Web.BackOffice.Controllers
                 });
 
             // Construct full URL using configured application URL (which will fall back to request)
-            var applicationUri = _requestAccessor.GetApplicationUrl();
+            var applicationUri = _hostingEnvironment.ApplicationMainUrl;
             var callbackUri = new Uri(applicationUri, action);
             return callbackUri.ToString();
         }
diff --git a/src/Umbraco.Web.BackOffice/Controllers/UsersController.cs b/src/Umbraco.Web.BackOffice/Controllers/UsersController.cs
index b543146f19..5e3d6b6791 100644
--- a/src/Umbraco.Web.BackOffice/Controllers/UsersController.cs
+++ b/src/Umbraco.Web.BackOffice/Controllers/UsersController.cs
@@ -54,7 +54,6 @@ namespace Umbraco.Web.BackOffice.Controllers
         private readonly ISqlContext _sqlContext;
         private readonly IImageUrlGenerator _imageUrlGenerator;
         private readonly SecuritySettings _securitySettings;
-        private readonly IRequestAccessor _requestAccessor;
         private readonly IEmailSender _emailSender;
         private readonly IBackOfficeSecurityAccessor _backofficeSecurityAccessor;
         private readonly AppCaches _appCaches;
@@ -77,7 +76,6 @@ namespace Umbraco.Web.BackOffice.Controllers
             ISqlContext sqlContext,
             IImageUrlGenerator imageUrlGenerator,
             IOptions<SecuritySettings> securitySettings,
-            IRequestAccessor requestAccessor,
             IEmailSender emailSender,
             IBackOfficeSecurityAccessor backofficeSecurityAccessor,
             AppCaches appCaches,
@@ -98,7 +96,6 @@ namespace Umbraco.Web.BackOffice.Controllers
             _sqlContext = sqlContext;
             _imageUrlGenerator = imageUrlGenerator;
             _securitySettings = securitySettings.Value;
-            _requestAccessor = requestAccessor;
             _emailSender = emailSender;
             _backofficeSecurityAccessor = backofficeSecurityAccessor;
             _appCaches = appCaches;
@@ -566,7 +563,7 @@ namespace Umbraco.Web.BackOffice.Controllers
                 });
 
             // Construct full URL using configured application URL (which will fall back to request)
-            var applicationUri = _requestAccessor.GetApplicationUrl();
+            var applicationUri = _hostingEnvironment.ApplicationMainUrl;
             var inviteUri = new Uri(applicationUri, action);
 
             var emailSubject = _localizedTextService.Localize("user/inviteEmailCopySubject",
diff --git a/src/Umbraco.Web.Common/AspNetCore/AspNetCoreHostingEnvironment.cs b/src/Umbraco.Web.Common/AspNetCore/AspNetCoreHostingEnvironment.cs
index 64e5e92e38..cdac7c562e 100644
--- a/src/Umbraco.Web.Common/AspNetCore/AspNetCoreHostingEnvironment.cs
+++ b/src/Umbraco.Web.Common/AspNetCore/AspNetCoreHostingEnvironment.cs
@@ -1,4 +1,5 @@
 using System;
+using System.Collections.Generic;
 using System.IO;
 using Microsoft.AspNetCore.Hosting;
 using Microsoft.Extensions.Options;
@@ -10,14 +11,20 @@ namespace Umbraco.Web.Common.AspNetCore
 {
     public class AspNetCoreHostingEnvironment : Core.Hosting.IHostingEnvironment
     {
-        private IOptionsMonitor<HostingSettings> _hostingSettings;
+        private readonly ISet<Uri> _applicationUrls = new HashSet<Uri>();
+        private readonly IOptionsMonitor<HostingSettings> _hostingSettings;
+        private readonly IOptionsMonitor<WebRoutingSettings> _webRoutingSettings;
         private readonly IWebHostEnvironment _webHostEnvironment;
 
         private string _localTempPath;
 
-        public AspNetCoreHostingEnvironment(IOptionsMonitor<HostingSettings> hostingSettings, IWebHostEnvironment webHostEnvironment)
+        public AspNetCoreHostingEnvironment(
+            IOptionsMonitor<HostingSettings> hostingSettings,
+            IOptionsMonitor<WebRoutingSettings> webRoutingSettings,
+            IWebHostEnvironment webHostEnvironment)
         {
             _hostingSettings = hostingSettings ?? throw new ArgumentNullException(nameof(hostingSettings));
+            _webRoutingSettings = webRoutingSettings ?? throw new ArgumentNullException(nameof(webRoutingSettings));
             _webHostEnvironment = webHostEnvironment ?? throw new ArgumentNullException(nameof(webHostEnvironment));
 
             SiteName = webHostEnvironment.ApplicationName;
@@ -28,6 +35,9 @@ namespace Umbraco.Web.Common.AspNetCore
         /// <inheritdoc/>
         public bool IsHosted { get; } = true;
 
+        /// <inheritdoc/>
+        public Uri ApplicationMainUrl { get; private set; }
+
         /// <inheritdoc/>
         public string SiteName { get; }
 
@@ -37,8 +47,6 @@ namespace Umbraco.Web.Common.AspNetCore
         /// <inheritdoc/>
         public string ApplicationPhysicalPath { get; }
 
-        public string ApplicationServerAddress { get; }
-
         // TODO how to find this, This is a server thing, not application thing.
         public string ApplicationVirtualPath => _hostingSettings.CurrentValue.ApplicationVirtualPath?.EnsureStartsWith('/') ?? "/";
 
@@ -123,6 +131,35 @@ namespace Umbraco.Web.Common.AspNetCore
 
             return fullPath;
         }
+
+        public void EnsureApplicationMainUrl(Uri currentApplicationUrl)
+        {
+            // Fixme: This causes problems with site swap on azure because azure pre-warms a site by calling into `localhost` and when it does that
+            // it changes the URL to `localhost:80` which actually doesn't work for pinging itself, it only works internally in Azure. The ironic part
+            // about this is that this is here specifically for the slot swap scenario https://issues.umbraco.org/issue/U4-10626
+
+            // see U4-10626 - in some cases we want to reset the application url
+            // (this is a simplified version of what was in 7.x)
+            // note: should this be optional? is it expensive?
+
+            if (currentApplicationUrl == null)
+            {
+                return;
+            }
+
+            if (!(_webRoutingSettings.CurrentValue.UmbracoApplicationUrl is null))
+            {
+                return;
+            }
+
+            var change = currentApplicationUrl != null && !_applicationUrls.Contains(currentApplicationUrl);
+            if (change)
+            {
+                _applicationUrls.Add(currentApplicationUrl);
+
+                ApplicationMainUrl = currentApplicationUrl;
+            }
+        }
     }
 
 
diff --git a/src/Umbraco.Web.Common/DependencyInjection/UmbracoBuilderExtensions.cs b/src/Umbraco.Web.Common/DependencyInjection/UmbracoBuilderExtensions.cs
index 7476a83167..ba6cbe03a9 100644
--- a/src/Umbraco.Web.Common/DependencyInjection/UmbracoBuilderExtensions.cs
+++ b/src/Umbraco.Web.Common/DependencyInjection/UmbracoBuilderExtensions.cs
@@ -382,9 +382,11 @@ namespace Umbraco.Web.Common.DependencyInjection
         private static IHostingEnvironment GetTemporaryHostingEnvironment(IWebHostEnvironment webHostEnvironment, IConfiguration config)
         {
             var hostingSettings = config.GetSection(Core.Constants.Configuration.ConfigHosting).Get<HostingSettings>() ?? new HostingSettings();
+            var webRoutingSettings = config.GetSection(Core.Constants.Configuration.ConfigWebRouting).Get<WebRoutingSettings>() ?? new WebRoutingSettings();
             var wrappedHostingSettings = new OptionsMonitorAdapter<HostingSettings>(hostingSettings);
+            var wrappedWebRoutingSettings = new OptionsMonitorAdapter<WebRoutingSettings>(webRoutingSettings);
 
-            return new AspNetCoreHostingEnvironment(wrappedHostingSettings, webHostEnvironment);
+            return new AspNetCoreHostingEnvironment(wrappedHostingSettings,wrappedWebRoutingSettings, webHostEnvironment);
         }
     }
 }
diff --git a/src/Umbraco.Web.Common/Middleware/UmbracoRequestMiddleware.cs b/src/Umbraco.Web.Common/Middleware/UmbracoRequestMiddleware.cs
index cee2d0e6e7..5dc604fea9 100644
--- a/src/Umbraco.Web.Common/Middleware/UmbracoRequestMiddleware.cs
+++ b/src/Umbraco.Web.Common/Middleware/UmbracoRequestMiddleware.cs
@@ -8,6 +8,7 @@ using Microsoft.Extensions.Logging;
 using Umbraco.Core;
 using Umbraco.Core.Cache;
 using Umbraco.Core.Events;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.Logging;
 using Umbraco.Extensions;
 using Umbraco.Web.Common.Profiler;
@@ -36,6 +37,7 @@ namespace Umbraco.Web.Common.Middleware
         private readonly IBackOfficeSecurityFactory _backofficeSecurityFactory;
         private readonly PublishedSnapshotServiceEventHandler _publishedSnapshotServiceEventHandler;
         private readonly IEventAggregator _eventAggregator;
+        private readonly IHostingEnvironment _hostingEnvironment;
         private readonly WebProfiler _profiler;
         private static bool s_cacheInitialized = false;
         private static bool s_cacheInitializedFlag = false;
@@ -51,7 +53,8 @@ namespace Umbraco.Web.Common.Middleware
             IBackOfficeSecurityFactory backofficeSecurityFactory,
             PublishedSnapshotServiceEventHandler publishedSnapshotServiceEventHandler,
             IEventAggregator eventAggregator,
-            IProfiler profiler)
+            IProfiler profiler,
+            IHostingEnvironment hostingEnvironment)
         {
             _logger = logger;
             _umbracoContextFactory = umbracoContextFactory;
@@ -59,6 +62,7 @@ namespace Umbraco.Web.Common.Middleware
             _backofficeSecurityFactory = backofficeSecurityFactory;
             _publishedSnapshotServiceEventHandler = publishedSnapshotServiceEventHandler;
             _eventAggregator = eventAggregator;
+            _hostingEnvironment = hostingEnvironment;
             _profiler = profiler as WebProfiler; // Ignore if not a WebProfiler
         }
 
@@ -81,6 +85,10 @@ namespace Umbraco.Web.Common.Middleware
             _backofficeSecurityFactory.EnsureBackOfficeSecurity();  // Needs to be before UmbracoContext, TODO: Why?
             UmbracoContextReference umbracoContextReference = _umbracoContextFactory.EnsureUmbracoContext();
 
+            Uri currentApplicationUrl = GetApplicationUrlFromCurrentRequest(context.Request);
+            _hostingEnvironment.EnsureApplicationMainUrl(currentApplicationUrl);
+
+
             bool isFrontEndRequest = umbracoContextReference.UmbracoContext.IsFrontEndUmbracoRequest();
 
             var pathAndQuery = context.Request.GetEncodedPathAndQuery();
@@ -138,6 +146,18 @@ namespace Umbraco.Web.Common.Middleware
             _profiler?.UmbracoApplicationEndRequest(context);
         }
 
+        private Uri GetApplicationUrlFromCurrentRequest(HttpRequest request)
+        {
+            // We only consider GET and POST.
+            // Especially the DEBUG sent when debugging the application is annoying because it uses http, even when the https is available.
+            if (request.Method == "GET" || request.Method == "POST")
+            {
+                return new Uri($"{request.Scheme}://{request.Host}{request.PathBase}", UriKind.Absolute);
+
+            }
+            return null;
+        }
+
         /// <summary>
         /// Any object that is in the HttpContext.Items collection that is IDisposable will get disposed on the end of the request
         /// </summary>
diff --git a/src/Umbraco.Web/AspNet/AspNetHostingEnvironment.cs b/src/Umbraco.Web/AspNet/AspNetHostingEnvironment.cs
index 6e0bca8af5..a58a5f3a14 100644
--- a/src/Umbraco.Web/AspNet/AspNetHostingEnvironment.cs
+++ b/src/Umbraco.Web/AspNet/AspNetHostingEnvironment.cs
@@ -17,6 +17,7 @@ namespace Umbraco.Web.Hosting
 
         private readonly HostingSettings _hostingSettings;
         private string _localTempPath;
+        private Uri _applicationMainUrl;
 
 
         public AspNetHostingEnvironment(IOptions<HostingSettings> hostingSettings)
@@ -41,6 +42,12 @@ namespace Umbraco.Web.Hosting
         /// <inheritdoc/>
         public bool IsHosted => (HttpContext.Current != null || HostingEnvironment.IsHosted);
 
+        public Uri ApplicationMainUrl
+        {
+            get => _applicationMainUrl;
+            set => _applicationMainUrl = value;
+        }
+
         public string MapPathWebRoot(string path)
         {
             if (HostingEnvironment.IsHosted)
@@ -54,6 +61,7 @@ namespace Umbraco.Web.Hosting
         public string MapPathContentRoot(string path) => MapPathWebRoot(path);
 
         public string ToAbsolute(string virtualPath) => VirtualPathUtility.ToAbsolute(virtualPath, ApplicationVirtualPath);
+        public void EnsureApplicationMainUrl(Uri currentApplicationUrl) => throw new NotImplementedException();
 
 
         public string LocalTempPath