diff --git a/src/Umbraco.Web/HealthCheck/Checks/Security/UmbracoApplicationUrlCheck.cs b/src/Umbraco.Web/HealthCheck/Checks/Security/UmbracoApplicationUrlCheck.cs
new file mode 100644
index 0000000000..f5e571a86a
--- /dev/null
+++ b/src/Umbraco.Web/HealthCheck/Checks/Security/UmbracoApplicationUrlCheck.cs
@@ -0,0 +1,101 @@
+using System;
+using System.Collections.Generic;
+using Umbraco.Core;
+using Umbraco.Core.Configuration.UmbracoSettings;
+using Umbraco.Core.IO;
+using Umbraco.Core.Services;
+using Umbraco.Web.HealthCheck.Checks.Config;
+
+namespace Umbraco.Web.HealthCheck.Checks.Security
+{
+    [HealthCheck(
+        "6708CA45-E96E-40B8-A40A-0607C1CA7F28",
+        "Application URL Configuration",
+        Description = "Checks if the Umbraco application URL is configured for your site.",
+        Group = "Security")]
+    public class UmbracoApplicationUrlCheck : HealthCheck
+    {
+        private readonly ILocalizedTextService _textService;
+        private readonly IRuntimeState _runtime;
+        private readonly IUmbracoSettingsSection _settings;
+
+        private const string SetApplicationUrlAction = "setApplicationUrl";
+
+        public UmbracoApplicationUrlCheck(ILocalizedTextService textService, IRuntimeState runtime, IUmbracoSettingsSection settings)
+        {
+            _textService = textService;
+            _runtime = runtime;
+            _settings = settings;
+        }
+
+        /// <summary>
+        /// Executes the action and returns its status
+        /// </summary>
+        /// <param name="action"></param>
+        /// <returns></returns>
+        public override HealthCheckStatus ExecuteAction(HealthCheckAction action)
+        {
+            switch (action.Alias)
+            {
+                case SetApplicationUrlAction:
+                    return SetUmbracoApplicationUrl();
+                default:
+                    throw new InvalidOperationException("UmbracoApplicationUrlCheck action requested is either not executable or does not exist");
+            }
+        }
+
+        public override IEnumerable<HealthCheckStatus> GetStatus()
+        {
+            //return the statuses
+            return new[] { CheckUmbracoApplicationUrl() };
+        }
+
+        private HealthCheckStatus CheckUmbracoApplicationUrl()
+        {
+            var urlConfigured = !_settings.WebRouting.UmbracoApplicationUrl.IsNullOrWhiteSpace();
+            var actions = new List<HealthCheckAction>();
+
+            string resultMessage = _textService.Localize("healthcheck", "umbracoApplicationUrlCheckResult", new[] { urlConfigured ? string.Empty : "not" });
+            StatusResultType resultType = urlConfigured ? StatusResultType.Success : StatusResultType.Warning;
+
+            if (urlConfigured == false)
+            {
+                actions.Add(new HealthCheckAction(SetApplicationUrlAction, Id)
+                {
+                    Name = _textService.Localize("healthcheck", "umbracoApplicationUrlConfigureButton"),
+                    Description = _textService.Localize("healthcheck", "umbracoApplicationUrlConfigureDescription")
+                });
+            }
+
+            return new HealthCheckStatus(resultMessage)
+            {
+                ResultType = resultType,
+                Actions = actions
+            };
+        }
+
+        private HealthCheckStatus SetUmbracoApplicationUrl()
+        {
+            var configFilePath = IOHelper.MapPath("~/config/umbracoSettings.config");
+            const string xPath = "/settings/web.routing/@umbracoApplicationUrl";
+            var configurationService = new ConfigurationService(configFilePath, xPath, _textService);
+            var urlValue = _runtime.ApplicationUrl.ToString();
+            var updateConfigFile = configurationService.UpdateConfigFile(urlValue);
+
+            if (updateConfigFile.Success)
+            {
+                return
+                    new HealthCheckStatus(_textService.Localize("healthcheck", "umbracoApplicationUrlConfigureSuccess", new[] { urlValue }))
+                    {
+                        ResultType = StatusResultType.Success
+                    };
+            }
+
+            return
+               new HealthCheckStatus(_textService.Localize("healthcheck", "umbracoApplicationUrlConfigureError", new[] { updateConfigFile.Result }))
+               {
+                   ResultType = StatusResultType.Error
+               };
+        }
+    }
+}
diff --git a/src/Umbraco.Web/Umbraco.Web.csproj b/src/Umbraco.Web/Umbraco.Web.csproj
index 5c84e65514..89317e8f99 100644
--- a/src/Umbraco.Web/Umbraco.Web.csproj
+++ b/src/Umbraco.Web/Umbraco.Web.csproj
@@ -190,6 +190,7 @@
     <Compile Include="HealthCheck\Checks\Config\ProvidedValueValidation.cs" />
     <Compile Include="Editors\TinyMceController.cs" />
     <Compile Include="HealthCheck\Checks\Data\DatabaseIntegrityCheck.cs" />
+    <Compile Include="HealthCheck\Checks\Security\UmbracoApplicationUrlCheck.cs" />
     <Compile Include="ImageCropperTemplateCoreExtensions.cs" />
     <Compile Include="Install\InstallSteps\TelemetryIdentifierStep.cs" />
     <Compile Include="IUmbracoContextFactory.cs" />