diff --git a/appmonitoring/validation-helm/test-apps/dotnet/Dockerfile.windows b/appmonitoring/validation-helm/test-apps/dotnet/Dockerfile.windows
new file mode 100644
index 000000000..a494e58b7
--- /dev/null
+++ b/appmonitoring/validation-helm/test-apps/dotnet/Dockerfile.windows
@@ -0,0 +1,51 @@
+# escape=`
+
+# Multi-layer image supporting Windows Server 2022 and Windows Server 2019
+# Note: .NET 8.0 uses Nano Server for 2022 and Server Core for 2019 (Nano Server 2019 not available for .NET 8.0)
+# 
+# Build commands:
+# For Windows Server 2022 only: docker build -f Dockerfile.windows --target final-2022 -t appmonitoring.azurecr.io/demoaks-dotnet-app-win:2022-latest .
+# For Windows Server 2019 only: docker build -f Dockerfile.windows --target final-2019 -t appmonitoring.azurecr.io/demoaks-dotnet-app-win:2019-latest .
+#
+# RECOMMENDED: Use build-multi-windows.ps1 script for multi-architecture manifest:
+# .\build-multi-windows.ps1 -Push -CreateManifest
+# 
+# Or with custom image name and tag:
+# .\build-multi-windows.ps1 -ImageName "appmonitoring.azurecr.io/demoaks-dotnet-app-win" -Tag "v1.0" -Push -CreateManifest
+#
+# This creates a single manifest tag (e.g., :latest) that automatically selects the correct 
+# Windows version image based on the pulling host's OS version. Individual platform images 
+# are only accessible by digest (no visible tags in the registry).
+#
+# cd C:\Program Files\Docker\Docker && DockerCli.exe -SwitchWindowsEngine
+# cd C:\Program Files\Docker\Docker && DockerCli.exe -SwitchLinuxEngine
+
+# BUILD STAGE (Common for both versions - using Server Core for tooling)
+FROM mcr.microsoft.com/dotnet/sdk:8.0-windowsservercore-ltsc2022 AS build
+WORKDIR C:\src
+COPY . .
+RUN dotnet restore
+RUN dotnet publish -c Release -o C:\out
+
+# BASE IMAGES for different Windows versions
+# Note: .NET 8.0 only supports Nano Server for LTSC2022, using Server Core for LTSC2019
+FROM mcr.microsoft.com/dotnet/aspnet:8.0-nanoserver-ltsc2022 AS base-2022
+WORKDIR C:\app
+
+FROM mcr.microsoft.com/dotnet/aspnet:8.0-windowsservercore-ltsc2019 AS base-2019
+WORKDIR C:\app
+
+# FINAL IMAGES
+FROM base-2022 AS final-2022
+WORKDIR C:\app
+COPY --from=build C:\out .
+EXPOSE 3001
+ENV ASPNETCORE_URLS=http://+:3001
+CMD ["dotnet", "dotnet-test-app.dll"]
+
+FROM base-2019 AS final-2019
+WORKDIR C:\app
+COPY --from=build C:\out .
+EXPOSE 3001
+ENV ASPNETCORE_URLS=http://+:3001
+CMD ["dotnet", "dotnet-test-app.dll"]
\ No newline at end of file
diff --git a/appmonitoring/validation-helm/test-apps/dotnet/build-multi-windows.ps1 b/appmonitoring/validation-helm/test-apps/dotnet/build-multi-windows.ps1
new file mode 100644
index 000000000..1735e7497
--- /dev/null
+++ b/appmonitoring/validation-helm/test-apps/dotnet/build-multi-windows.ps1
@@ -0,0 +1,205 @@
+# Multi-Windows Version Docker Build Script
+# This script builds Docker images for both Windows 2022 and Windows 2019
+
+param(
+    [string]$ImageName = "appmonitoring.azurecr.io/demoaks-dotnet-app-win",
+    [string]$Tag = "latest",
+    [switch]$Push,
+    [switch]$CreateManifest
+)
+
+$ErrorActionPreference = "Stop"
+
+Write-Host "Building multi-Windows Docker images..." -ForegroundColor Green
+Write-Host "Image Name: $ImageName" -ForegroundColor Yellow
+Write-Host "Tag: $Tag" -ForegroundColor Yellow
+
+# Switch to Windows containers
+Write-Host "Switching to Windows containers..." -ForegroundColor Cyan
+& "C:\Program Files\Docker\Docker\DockerCli.exe" -SwitchWindowsEngine
+
+# Build Windows 2022 image
+Write-Host "Building Windows 2022 image..." -ForegroundColor Cyan
+$localImage2022 = "local-win2022-$(Get-Random)"
+docker build -f Dockerfile.windows --target final-2022 -t $localImage2022 .
+if ($LASTEXITCODE -ne 0) {
+    throw "Failed to build Windows 2022 image"
+}
+
+# Build Windows 2019 image
+Write-Host "Building Windows 2019 image..." -ForegroundColor Cyan
+$localImage2019 = "local-win2019-$(Get-Random)"
+docker build -f Dockerfile.windows --target final-2019 -t $localImage2019 .
+if ($LASTEXITCODE -ne 0) {
+    throw "Failed to build Windows 2019 image"
+}
+
+Write-Host "Successfully built both images:" -ForegroundColor Green
+Write-Host "  - $localImage2022" -ForegroundColor Yellow
+Write-Host "  - $localImage2019" -ForegroundColor Yellow
+
+if ($Push) {
+    if ($CreateManifest) {
+        Write-Host "Pushing images with platform-specific tags..." -ForegroundColor Cyan
+        
+        # Use clear, descriptive platform-specific tags
+        $platformTag2022 = "${ImageName}:ltsc2022"
+        $platformTag2019 = "${ImageName}:ltsc2019"
+        
+        # Tag and push Windows 2022 image
+        Write-Host "Pushing Windows Server 2022 image..." -ForegroundColor Yellow
+        docker tag $localImage2022 $platformTag2022
+        docker push $platformTag2022
+        if ($LASTEXITCODE -ne 0) {
+            throw "Failed to push Windows Server 2022 image"
+        }
+        
+        # Tag and push Windows 2019 image
+        Write-Host "Pushing Windows Server 2019 image..." -ForegroundColor Yellow
+        docker tag $localImage2019 $platformTag2019
+        docker push $platformTag2019
+        if ($LASTEXITCODE -ne 0) {
+            throw "Failed to push Windows Server 2019 image"
+        }
+        
+        Write-Host "Successfully pushed platform-specific images:" -ForegroundColor Green
+        Write-Host "  - $platformTag2022" -ForegroundColor Yellow
+        Write-Host "  - $platformTag2019" -ForegroundColor Yellow
+        
+        # Extract OS versions from the actual images
+        Write-Host "Extracting OS versions from images..." -ForegroundColor Cyan
+        
+        # Try multiple methods to extract OS version for Windows 2022
+        $osVersion2022 = docker image inspect $platformTag2022 --format='{{.Os}}' 2>$null
+        if ($osVersion2022 -eq "windows") {
+            # Try to get OS version from different possible locations
+            $osVersion2022 = docker image inspect $platformTag2022 --format='{{index .Config.Labels "org.opencontainers.image.version"}}' 2>$null
+            if (-not $osVersion2022) {
+                $osVersion2022 = docker image inspect $platformTag2022 --format='{{.OsVersion}}' 2>$null
+            }
+            if (-not $osVersion2022) {
+                $osVersion2022 = docker image inspect $platformTag2022 --format='{{index .Config.Labels "os.version"}}' 2>$null
+            }
+            if (-not $osVersion2022) {
+                # Try to extract from base image info - look for LTSC2022 pattern
+                $imageConfig = docker image inspect $platformTag2022 --format='{{json .}}' | ConvertFrom-Json
+                if ($imageConfig.Config.Labels.PSObject.Properties.Name -contains "org.opencontainers.image.base.name") {
+                    $baseName = $imageConfig.Config.Labels."org.opencontainers.image.base.name"
+                    if ($baseName -match "ltsc2022") {
+                        $osVersion2022 = "10.0.20348"
+                    }
+                }
+            }
+        }
+        
+        if (-not $osVersion2022) {
+            throw "Could not extract OS version from Windows 2022 image: $platformTag2022. Try: docker image inspect $platformTag2022"
+        }
+        
+        # Try multiple methods to extract OS version for Windows 2019
+        $osVersion2019 = docker image inspect $platformTag2019 --format='{{.Os}}' 2>$null
+        if ($osVersion2019 -eq "windows") {
+            # Try to get OS version from different possible locations
+            $osVersion2019 = docker image inspect $platformTag2019 --format='{{index .Config.Labels "org.opencontainers.image.version"}}' 2>$null
+            if (-not $osVersion2019) {
+                $osVersion2019 = docker image inspect $platformTag2019 --format='{{.OsVersion}}' 2>$null
+            }
+            if (-not $osVersion2019) {
+                $osVersion2019 = docker image inspect $platformTag2019 --format='{{index .Config.Labels "os.version"}}' 2>$null
+            }
+            if (-not $osVersion2019) {
+                # Try to extract from base image info - look for LTSC2019 pattern
+                $imageConfig = docker image inspect $platformTag2019 --format='{{json .}}' | ConvertFrom-Json
+                if ($imageConfig.Config.Labels.PSObject.Properties.Name -contains "org.opencontainers.image.base.name") {
+                    $baseName = $imageConfig.Config.Labels."org.opencontainers.image.base.name"
+                    if ($baseName -match "ltsc2019") {
+                        $osVersion2019 = "10.0.17763"
+                    }
+                }
+            }
+        }
+        
+        if (-not $osVersion2019) {
+            throw "Could not extract OS version from Windows 2019 image: $platformTag2019. Try: docker image inspect $platformTag2019"
+        }
+        
+        Write-Host "Detected OS versions:" -ForegroundColor Green
+        Write-Host "  Windows 2022: $osVersion2022" -ForegroundColor Yellow
+        Write-Host "  Windows 2019: $osVersion2019" -ForegroundColor Yellow
+        
+        # Create manifest using platform-specific tag references
+        Write-Host "Creating multi-architecture manifest..." -ForegroundColor Cyan
+        $manifestName = "${ImageName}:win"
+        
+        docker manifest create --amend $manifestName $platformTag2022 $platformTag2019
+        if ($LASTEXITCODE -ne 0) {
+            throw "Failed to create manifest"
+        }
+        
+        # Annotate for Windows versions using detected OS versions
+        docker manifest annotate $manifestName $platformTag2022 --os windows --arch amd64 --os-version $osVersion2022
+        docker manifest annotate $manifestName $platformTag2019 --os windows --arch amd64 --os-version $osVersion2019
+        
+        # Push manifest
+        docker manifest push $manifestName
+        if ($LASTEXITCODE -ne 0) {
+            throw "Failed to push manifest"
+        }
+        
+        Write-Host "Successfully pushed manifest: $manifestName" -ForegroundColor Green
+        
+        # Clean up local images
+        Write-Host "Cleaning up local images..." -ForegroundColor Cyan
+        docker rmi $localImage2022 $localImage2019 -f 2>$null
+        
+        Write-Host "Successfully created and pushed manifest: $manifestName" -ForegroundColor Green
+        Write-Host "Platform-specific images:" -ForegroundColor Green
+        Write-Host "  - $platformTag2022" -ForegroundColor Yellow
+        Write-Host "  - $platformTag2019" -ForegroundColor Yellow
+        Write-Host "Multi-platform manifest: $manifestName" -ForegroundColor Green
+        
+    } else {
+        # Traditional push with user-friendly tags
+        Write-Host "Pushing images with user-friendly tags..." -ForegroundColor Cyan
+        
+        $image2022 = "${ImageName}:2022-${Tag}"
+        $image2019 = "${ImageName}:2019-${Tag}"
+        
+        docker tag $localImage2022 $image2022
+        docker tag $localImage2019 $image2019
+        
+        docker push $image2022
+        if ($LASTEXITCODE -ne 0) {
+            throw "Failed to push Windows 2022 image"
+        }
+        
+        docker push $image2019
+        if ($LASTEXITCODE -ne 0) {
+            throw "Failed to push Windows 2019 image"
+        }
+        
+        # Clean up local images
+        docker rmi $localImage2022 $localImage2019 -f 2>$null
+        
+        Write-Host "Successfully pushed both images with user-friendly tags" -ForegroundColor Green
+        Write-Host "  - $image2022" -ForegroundColor Yellow
+        Write-Host "  - $image2019" -ForegroundColor Yellow
+    }
+} else {
+    # If not pushing, create user-friendly local tags for development
+    $image2022 = "${ImageName}:2022-${Tag}"
+    $image2019 = "${ImageName}:2019-${Tag}"
+    docker tag $localImage2022 $image2022
+    docker tag $localImage2019 $image2019
+    docker rmi $localImage2022 $localImage2019 -f 2>$null
+    
+    Write-Host "Tagged images locally:" -ForegroundColor Green
+    Write-Host "  - $image2022" -ForegroundColor Yellow
+    Write-Host "  - $image2019" -ForegroundColor Yellow
+}
+
+# Switch back to Linux containers
+Write-Host "Switching back to Linux containers..." -ForegroundColor Cyan
+& "C:\Program Files\Docker\Docker\DockerCli.exe" -SwitchLinuxEngine
+
+Write-Host "Build completed successfully!" -ForegroundColor Green
\ No newline at end of file