diff --git a/src/Umbraco.Web/HealthCheck/Checks/Config/TrySkipIisCustomErrorsCheck.cs b/src/Umbraco.Abstractions/Configuration/HealthChecks/TrySkipIisCustomErrorsCheck.cs
similarity index 78%
rename from src/Umbraco.Web/HealthCheck/Checks/Config/TrySkipIisCustomErrorsCheck.cs
rename to src/Umbraco.Abstractions/Configuration/HealthChecks/TrySkipIisCustomErrorsCheck.cs
index 6cfbf18370..58172ba063 100644
--- a/src/Umbraco.Web/HealthCheck/Checks/Config/TrySkipIisCustomErrorsCheck.cs
+++ b/src/Umbraco.Abstractions/Configuration/HealthChecks/TrySkipIisCustomErrorsCheck.cs
@@ -1,8 +1,9 @@
 using System;
 using System.Collections.Generic;
 using System.Linq;
-using System.Web;
+using Umbraco.Core.Hosting;
 using Umbraco.Core.IO;
+using Umbraco.Core.Logging;
 using Umbraco.Core.Services;
 
 namespace Umbraco.Web.HealthCheck.Checks.Config
@@ -12,11 +13,14 @@ namespace Umbraco.Web.HealthCheck.Checks.Config
         Group = "Configuration")]
     public class TrySkipIisCustomErrorsCheck : AbstractConfigCheck
     {
-        private readonly Version _serverVersion = HttpRuntime.IISVersion;
+        private readonly IHostingEnvironment _hostingEnvironment;
 
-        public TrySkipIisCustomErrorsCheck(ILocalizedTextService textService, IIOHelper ioHelper)
-            : base(textService, ioHelper)
-        { }
+        public TrySkipIisCustomErrorsCheck(ILocalizedTextService textService, IIOHelper ioHelper, ILogger logger,
+            IHostingEnvironment hostingEnvironment)
+            : base(textService, ioHelper, logger)
+        {
+            _hostingEnvironment = hostingEnvironment;
+        }
 
         public override string FilePath => "~/Config/umbracoSettings.config";
 
@@ -29,7 +33,7 @@ namespace Umbraco.Web.HealthCheck.Checks.Config
             get
             {
                 // beware! 7.5 and 7.5.0 are not the same thing!
-                var recommendedValue = _serverVersion >= new Version("7.5")
+                var recommendedValue = _hostingEnvironment.IISVersion >= new Version("7.5")
                     ? bool.TrueString.ToLower()
                     : bool.FalseString.ToLower();
                 return new List<AcceptableConfiguration> { new AcceptableConfiguration { IsRecommended =  true, Value = recommendedValue } };
@@ -41,7 +45,7 @@ namespace Umbraco.Web.HealthCheck.Checks.Config
             get
             {
                 return TextService.Localize("healthcheck/trySkipIisCustomErrorsCheckSuccessMessage",
-                    new[] { Values.First(v => v.IsRecommended).Value, _serverVersion.ToString() });
+                    new[] { Values.First(v => v.IsRecommended).Value, _hostingEnvironment.IISVersion.ToString() });
             }
         }
 
@@ -50,7 +54,7 @@ namespace Umbraco.Web.HealthCheck.Checks.Config
             get
             {
                 return TextService.Localize("healthcheck/trySkipIisCustomErrorsCheckErrorMessage",
-                    new[] { CurrentValue, Values.First(v => v.IsRecommended).Value, _serverVersion.ToString() });
+                    new[] { CurrentValue, Values.First(v => v.IsRecommended).Value, _hostingEnvironment.IISVersion.ToString() });
             }
         }
 
@@ -59,7 +63,7 @@ namespace Umbraco.Web.HealthCheck.Checks.Config
             get
             {
                 return TextService.Localize("healthcheck/trySkipIisCustomErrorsCheckRectifySuccessMessage",
-                    new[] { Values.First(v => v.IsRecommended).Value, _serverVersion.ToString() });
+                    new[] { Values.First(v => v.IsRecommended).Value, _hostingEnvironment.IISVersion.ToString() });
             }
         }
     }
diff --git a/src/Umbraco.Abstractions/Hosting/IHostingEnvironment.cs b/src/Umbraco.Abstractions/Hosting/IHostingEnvironment.cs
index cf2667c121..1662879cf2 100644
--- a/src/Umbraco.Abstractions/Hosting/IHostingEnvironment.cs
+++ b/src/Umbraco.Abstractions/Hosting/IHostingEnvironment.cs
@@ -1,3 +1,5 @@
+using System;
+
 namespace Umbraco.Core.Hosting
 {
     public interface IHostingEnvironment
@@ -16,6 +18,7 @@ namespace Umbraco.Core.Hosting
         /// Gets a value indicating whether Umbraco is hosted.
         /// </summary>
         bool IsHosted { get; }
+        Version IISVersion { get; }
         string MapPath(string path);
         string ToAbsolute(string virtualPath, string root);
 
diff --git a/src/Umbraco.Web/Hosting/AspNetHostingEnvironment.cs b/src/Umbraco.Web/Hosting/AspNetHostingEnvironment.cs
index c9336546c5..f9b1f1019b 100644
--- a/src/Umbraco.Web/Hosting/AspNetHostingEnvironment.cs
+++ b/src/Umbraco.Web/Hosting/AspNetHostingEnvironment.cs
@@ -27,6 +27,7 @@ namespace Umbraco.Web.Hosting
             ApplicationPhysicalPath = HostingEnvironment.ApplicationPhysicalPath;
             ApplicationVirtualPath = HostingEnvironment.ApplicationVirtualPath;
             CurrentDomainId = AppDomain.CurrentDomain.Id;
+            IISVersion = HttpRuntime.IISVersion;
         }
 
         public int CurrentDomainId { get; }
@@ -39,6 +40,9 @@ namespace Umbraco.Web.Hosting
         public bool IsDebugMode => HttpContext.Current?.IsDebuggingEnabled ?? _hostingSettings.DebugMode;
         /// <inheritdoc/>
         public bool IsHosted => (HttpContext.Current != null || HostingEnvironment.IsHosted);
+
+        public Version IISVersion { get; }
+
         public string MapPath(string path)
         {
             return HostingEnvironment.MapPath(path);