diff --git a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/Environment.cpp b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/Environment.cpp
index 7096cf85b808..c49200ce8d2f 100644
--- a/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/Environment.cpp
+++ b/src/Servers/IIS/AspNetCoreModuleV2/CommonLib/Environment.cpp
@@ -231,7 +231,7 @@ bool Environment::CheckUpToDate(const std::wstring& source, const std::filesyste
             auto sourceInnerDirectory = std::filesystem::directory_entry(path);
             if (sourceInnerDirectory.path() != directoryToIgnore)
             {
-                CheckUpToDate(destination / path.path().filename(), path.path(), extension, directoryToIgnore);
+                CheckUpToDate(/* source */ path.path(), /* destination */ destination / path.path().filename(), extension, directoryToIgnore);
             }
         }
     }
diff --git a/src/Servers/IIS/IIS/test/IIS.ShadowCopy.Tests/ShadowCopyTests.cs b/src/Servers/IIS/IIS/test/IIS.ShadowCopy.Tests/ShadowCopyTests.cs
index f4b93e637b33..68dc2e78215b 100644
--- a/src/Servers/IIS/IIS/test/IIS.ShadowCopy.Tests/ShadowCopyTests.cs
+++ b/src/Servers/IIS/IIS/test/IIS.ShadowCopy.Tests/ShadowCopyTests.cs
@@ -142,6 +142,37 @@ public async Task ShadowCopySingleFileChangedWorks()
         Assert.True(response.IsSuccessStatusCode);
     }
 
+    [ConditionalFact]
+    public async Task ShadowCopyDeleteFolderDuringShutdownWorks()
+    {
+        using var directory = TempDirectory.Create();
+        var deploymentParameters = Fixture.GetBaseDeploymentParameters();
+        deploymentParameters.HandlerSettings["enableShadowCopy"] = "true";
+        deploymentParameters.HandlerSettings["shadowCopyDirectory"] = directory.DirectoryPath;
+
+        var deploymentResult = await DeployAsync(deploymentParameters);
+        var deleteDirPath = Path.Combine(deploymentResult.ContentRoot, "wwwroot/deletethis");
+        Directory.CreateDirectory(deleteDirPath);
+        File.WriteAllText(Path.Combine(deleteDirPath, "file.dll"), "");
+
+        var response = await deploymentResult.HttpClient.GetAsync("Wow!");
+        Assert.True(response.IsSuccessStatusCode);
+
+        AddAppOffline(deploymentResult.ContentRoot);
+        await AssertAppOffline(deploymentResult);
+
+        // Delete folder + file after app is shut down
+        // Testing specific path on startup where we compare the app directory contents with the shadow copy directory
+        Directory.Delete(deleteDirPath, recursive: true);
+
+        RemoveAppOffline(deploymentResult.ContentRoot);
+
+        await deploymentResult.AssertRecycledAsync();
+
+        response = await deploymentResult.HttpClient.GetAsync("Wow!");
+        Assert.True(response.IsSuccessStatusCode);
+    }
+
     [ConditionalFact]
     public async Task ShadowCopyE2EWorksWithFolderPresent()
     {