diff --git a/.gitignore b/.gitignore
index 1b76725e95..aee4edab51 100644
--- a/.gitignore
+++ b/.gitignore
@@ -16,4 +16,6 @@ work-pester-jenkins-windows/
 /**/windows/**/jenkins-plugin-cli.ps1
 /**/windows/**/jenkins-support.psm1
 
+build-windows_*.yaml
+
 tests/**/Dockerfile\.*
diff --git a/Jenkinsfile b/Jenkinsfile
index 61a25a1b23..2518e6931b 100644
--- a/Jenkinsfile
+++ b/Jenkinsfile
@@ -47,11 +47,15 @@ stage('Build') {
     withEnv(envVars) {
         echo '= bake target: linux'
 
-        def windowsImageTypes = ['windowsservercore-ltsc2022']
+        def windowsImageTypes = [
+            'windowsservercore-ltsc2022'
+        ]
         for (anImageType in windowsImageTypes) {
             def imageType = anImageType
             builds[imageType] = {
-                nodeWithTimeout('windows-2022') {
+                def windowsVersionNumber = imageType.split('-')[1].replace('ltsc', '')
+                def windowsLabel = "windows-${windowsVersionNumber}"
+                nodeWithTimeout(windowsLabel) {
                     stage('Checkout') {
                         checkout scm
                     }
@@ -63,13 +67,14 @@ stage('Build') {
                             */
                             stage("Build ${imageType}") {
                                 infra.withDockerCredentials {
-                                    powershell './make.ps1 build'
+                                    powershell './make.ps1 build -ImageType ${env:IMAGE_TYPE}'
+                                    archiveArtifacts artifacts: 'build-windows_*.yaml', allowEmptyArchive: true
                                 }
                             }
 
                             stage("Test ${imageType}") {
                                 infra.withDockerCredentials {
-                                    def windowsTestStatus = powershell(script: './make.ps1 test', returnStatus: true)
+                                    def windowsTestStatus = powershell(script: './make.ps1 test -ImageType ${env:IMAGE_TYPE}', returnStatus: true)
                                     junit(allowEmptyResults: true, keepLongStdio: true, testResults: 'target/**/junit-results.xml')
                                     if (windowsTestStatus > 0) {
                                         // If something bad happened let's clean up the docker images
@@ -102,8 +107,8 @@ stage('Build') {
                                     stage('Publish') {
                                         infra.withDockerCredentials {
                                             withEnv(['DOCKERHUB_ORGANISATION=jenkins', 'DOCKERHUB_REPO=jenkins']) {
-                                                powershell './make.ps1 build'
-                                                powershell './make.ps1 publish'
+                                                powershell './make.ps1 build -ImageType ${env:IMAGE_TYPE}'
+                                                powershell './make.ps1 publish -ImageType ${env:IMAGE_TYPE}'
                                             }
                                         }
                                     }
@@ -116,8 +121,7 @@ stage('Build') {
         }
 
         if (!infra.isTrusted()) {
-            // This list can be updated with the following command:
-            // make show | jq -r '.target | keys[]' | sort
+            // An up to date list can be obtained with make list-linux
             def images = [
                 'alpine_jdk21',
                 'alpine_jdk25',
diff --git a/Makefile b/Makefile
index 1b8a745233..4e52ea3057 100644
--- a/Makefile
+++ b/Makefile
@@ -9,7 +9,17 @@ export BUILDKIT_PROGRESS=plain
 ## Required to have the commit SHA added as a Docker image label
 export COMMIT_SHA=$(shell git rev-parse HEAD)
 
+current_os := $(shell uname -s)
 current_arch := $(shell uname -m)
+
+export OS ?= $(shell \
+	case "$(current_os)" in \
+		(Linux) echo linux ;; \
+		(Darwin) echo linux ;; \
+		(MINGW*|MSYS*|CYGWIN*) echo windows ;; \
+		(*) echo unknown ;; \
+	esac)
+
 export ARCH ?= $(shell \
 	case $(current_arch) in \
 		(x86_64) echo "amd64" ;; \
@@ -31,11 +41,11 @@ TEST_SUITES ?= $(CURDIR)/tests
 ## Check the presence of a CLI in the current PATH
 check_cli = type "$(1)" >/dev/null 2>&1 || { echo "Error: command '$(1)' required but not found. Exiting." ; exit 1 ; }
 ## Check if a given image exists in the current manifest docker-bake.hcl
-check_image = make --silent list | grep -w '$(1)' >/dev/null 2>&1 || { echo "Error: the image '$(1)' does not exist in manifest for the platform 'linux/$(ARCH)'. Please check the output of 'make list'. Exiting." ; exit 1 ; }
+check_image = make --silent list | grep -w '$(1)' >/dev/null 2>&1 || { echo "Error: the image '$(1)' does not exist in manifest for the current platform '$(OS)/$(ARCH)'. Please check the output of 'make list'. Exiting." ; exit 1 ; }
 ## Base "docker buildx base" command to be reused everywhere
 bake_base_cli := docker buildx bake -f docker-bake.hcl --load
 ## Default bake target
-bake_default_target := linux
+bake_default_target := all
 
 check-reqs:
 ## Build requirements
@@ -72,18 +82,18 @@ hadolint:
 shellcheck:
 	@$(ROOT_DIR)/tools/shellcheck -e SC1091 jenkins-support *.sh tests/test_helpers.bash tools/hadolint tools/shellcheck .ci/publish.sh
 
-# Build targets depending on the current architecture
+# Build all targets with the current OS and architecture
 build: check-reqs target
-	@set -x; $(bake_base_cli) --metadata-file=target/build-result-metadata_$(bake_default_target).json --set '*.platform=linux/$(ARCH)' $(shell make --silent list)
+	@set -x; $(bake_base_cli) --metadata-file=target/build-result-metadata_$(bake_default_target).json --set '*.platform=$(OS)/$(ARCH)' $(shell make --silent list)
 
-# Build targets depending on the architecture
+# Build targets depending on the architecture (Linux only, no multiarch for Windows)
 buildarch-%: check-reqs target showarch-%
 	@set -x; $(bake_base_cli) --metadata-file=target/build-result-metadata_$*.json --set '*.platform=linux/$*' $(shell make --silent listarch-$*)
 
-# Build a specific target with the current architecture
+# Build a specific target with the current OS and architecture
 build-%: check-reqs target show-%
 	@$(call check_image,$*)
-	@set -x; $(bake_base_cli) --metadata-file=target/build-result-metadata_$*.json --set '*.platform=linux/$(ARCH)' '$*'
+	@set -x; $(bake_base_cli) --metadata-file=target/build-result-metadata_$*.json --set '*.platform=$(OS)/$(ARCH)' '$*'
 
 # Show all targets
 show:
@@ -91,25 +101,37 @@ show:
 
 # Show a specific target
 show-%:
-	@set -x; $(bake_base_cli) --progress=quiet $* --print | jq
+	@set -x; $(bake_base_cli) --progress=quiet '$*' --print | jq
 
 # Show all targets depending on the architecture
 showarch-%:
-	@set -x; make --silent show | jq --arg arch "linux/$*" '.target |= with_entries(select(.value.platforms | index($$arch)))'
+	@set -x; make --silent show | jq --arg arch "$(OS)/$*" '.target |= with_entries(select(.value.platforms | index($$arch)))'
 
-# List all tags
+# List tags of all targets
 tags:
-	@set -x; make show | jq -r ' .target | to_entries[] | .key as $$name | .value.tags[] | "\(.) (\($$name))"' | LC_ALL=C sort -u
+	@set -x; make tags-$(bake_default_target)
+
+# List tags of a specific target
+tags-%:
+	@set -x; make show-$* | jq -r ' .target | to_entries[] | .key as $$name | .value.tags[] | "\(.) (\($$name))"' | LC_ALL=C sort -u
 
 # List all platforms
 platforms:
-	@set -x; make show | jq -r ' .target | to_entries[] | .key as $$name | .value.platforms[] | "\($$name):\(.)"' | LC_ALL=C sort -u
+	@set -x; make platforms-$(bake_default_target)
+
+# List platforms of a specific target
+platforms-%:
+	@set -x; make show-$* | jq -r ' .target | to_entries[] | .key as $$name | .value.platforms[] | "\($$name):\(.)"' | LC_ALL=C sort -u
 
-# Return the list of targets depending on the current architecture
+# Return the list of targets depending on the current OS and architecture
 list: check-reqs
-	@set -x; make --silent showarch-$(ARCH) | jq -r '.target | keys[]'
+	@set -x; make --silent listarch-$(ARCH)
+
+# Return the list of targets of a specific "target" (can be a docker bake group)
+list-%: check-reqs
+	@set -x; make --silent show-$* | jq -r '.target | keys[]'
 
-# Return the list of targets depending on the architecture
+# Return the list of targets depending on the architecture (Linux only, no multiarch for Windows)
 listarch-%: check-reqs
 	@set -x; make --silent showarch-$* | jq -r '.target | keys[]'
 
diff --git a/build-windows.yaml b/build-windows.yaml
deleted file mode 100644
index 1515a5397e..0000000000
--- a/build-windows.yaml
+++ /dev/null
@@ -1,35 +0,0 @@
-services:
-  jdk21:
-    image: ${DOCKERHUB_ORGANISATION}/${DOCKERHUB_REPO}${SEPARATOR_LTS_PREFIX}jdk21-hotspot-${WINDOWS_FLAVOR}-${WINDOWS_VERSION}
-    build:
-      context: ./
-      dockerfile: ./windows/${WINDOWS_FLAVOR}/hotspot/Dockerfile
-      args:
-        COMMIT_SHA: ${COMMIT_SHA}
-        JAVA_HOME: "C:/openjdk-21"
-        JAVA_VERSION: 21.0.9_10
-        WAR_SHA: ${WAR_SHA}
-        JENKINS_VERSION: ${JENKINS_VERSION}
-        WAR_URL: ${WAR_URL}
-        WINDOWS_VERSION: ${WINDOWS_VERSION}
-      tags:
-        - ${DOCKERHUB_ORGANISATION}/${DOCKERHUB_REPO}:${JENKINS_VERSION}-jdk21-hotspot-${WINDOWS_FLAVOR}-${WINDOWS_VERSION}
-        - ${DOCKERHUB_ORGANISATION}/${DOCKERHUB_REPO}:${JENKINS_VERSION}-${WINDOWS_FLAVOR}-${WINDOWS_VERSION}
-        - ${DOCKERHUB_ORGANISATION}/${DOCKERHUB_REPO}${SEPARATOR_LTS_PREFIX}${WINDOWS_FLAVOR}-${WINDOWS_VERSION}
-  jdk25:
-    image: ${DOCKERHUB_ORGANISATION}/${DOCKERHUB_REPO}${SEPARATOR_LTS_PREFIX}jdk25-hotspot-${WINDOWS_FLAVOR}-${WINDOWS_VERSION}
-    build:
-      context: ./
-      dockerfile: ./windows/${WINDOWS_FLAVOR}/hotspot/Dockerfile
-      args:
-        COMMIT_SHA: ${COMMIT_SHA}
-        JAVA_HOME: "C:/openjdk-25"
-        JAVA_VERSION: 25.0.1_8
-        WAR_SHA: ${WAR_SHA}
-        JENKINS_VERSION: ${JENKINS_VERSION}
-        WAR_URL: ${WAR_URL}
-        WINDOWS_VERSION: ${WINDOWS_VERSION}
-      tags:
-        - ${DOCKERHUB_ORGANISATION}/${DOCKERHUB_REPO}:${JENKINS_VERSION}-jdk25-hotspot-${WINDOWS_FLAVOR}-${WINDOWS_VERSION}
-        - ${DOCKERHUB_ORGANISATION}/${DOCKERHUB_REPO}:${JENKINS_VERSION}-${WINDOWS_FLAVOR}-${WINDOWS_VERSION}
-        - ${DOCKERHUB_ORGANISATION}/${DOCKERHUB_REPO}${SEPARATOR_LTS_PREFIX}${WINDOWS_FLAVOR}-${WINDOWS_VERSION}
diff --git a/docker-bake.hcl b/docker-bake.hcl
index cc8a77faa3..901dab9035 100644
--- a/docker-bake.hcl
+++ b/docker-bake.hcl
@@ -7,6 +7,14 @@ variable "jdks_to_build_for_weekly" {
   default = [21, 25]
 }
 
+variable "windows_version_to_build_for_lts" {
+  default = ["windowsservercore-ltsc2019"]
+}
+
+variable "windows_version_to_build_for_weekly" {
+  default = ["windowsservercore-ltsc2022"]
+}
+
 variable "default_jdk" {
   default = 21
 }
@@ -83,6 +91,11 @@ variable "RHEL_RELEASE_LINE" {
   default = "ubi9"
 }
 
+# Set this value to a specific Windows version to override Windows versions to build returned by windowsversions function
+variable "WINDOWS_VERSION_OVERRIDE" {
+  default = ""
+}
+
 ## Internal variables
 variable "jdk_versions" {
   default = {
@@ -114,8 +127,8 @@ target "alpine" {
     WAR_URL            = war_url()
     COMMIT_SHA         = COMMIT_SHA
     PLUGIN_CLI_VERSION = PLUGIN_CLI_VERSION
-    ALPINE_TAG         = ALPINE_FULL_TAG
     JAVA_VERSION       = javaversion(jdk)
+    ALPINE_TAG         = ALPINE_FULL_TAG
   }
   tags      = linux_tags("alpine", jdk)
   platforms = platforms("alpine", jdk)
@@ -135,10 +148,10 @@ target "debian" {
     WAR_URL             = war_url()
     COMMIT_SHA          = COMMIT_SHA
     PLUGIN_CLI_VERSION  = PLUGIN_CLI_VERSION
+    JAVA_VERSION        = javaversion(jdk)
     DEBIAN_RELEASE_LINE = DEBIAN_RELEASE_LINE
     DEBIAN_VERSION      = DEBIAN_VERSION
     DEBIAN_VARIANT      = is_debian_slim(variant) ? "-slim" : ""
-    JAVA_VERSION        = javaversion(jdk)
   }
   tags      = linux_tags(variant, jdk)
   platforms = platforms(variant, jdk)
@@ -157,14 +170,36 @@ target "rhel" {
     WAR_URL            = war_url()
     COMMIT_SHA         = COMMIT_SHA
     PLUGIN_CLI_VERSION = PLUGIN_CLI_VERSION
+    JAVA_VERSION       = javaversion(jdk)
     RHEL_TAG           = RHEL_TAG
     RHEL_RELEASE_LINE  = RHEL_RELEASE_LINE
-    JAVA_VERSION       = javaversion(jdk)
   }
   tags      = linux_tags(current_rhel, jdk)
   platforms = platforms(current_rhel, jdk)
 }
 
+target "windowsservercore" {
+  matrix = {
+    jdk             = jdks_to_build()
+    windows_version = windowsversions()
+  }
+  name       = "${windows_version}_jdk${jdk}"
+  dockerfile = "windows/windowsservercore/hotspot/Dockerfile"
+  context    = "."
+  args = {
+    JENKINS_VERSION    = JENKINS_VERSION
+    WAR_SHA            = WAR_SHA
+    WAR_URL            = war_url()
+    COMMIT_SHA         = COMMIT_SHA
+    PLUGIN_CLI_VERSION = PLUGIN_CLI_VERSION
+    JAVA_VERSION       = javaversion(jdk)
+    JAVA_HOME          = "C:/openjdk-${jdk}"
+    WINDOWS_VERSION    = windows_version
+  }
+  tags      = windows_tags(windows_version, jdk)
+  platforms = ["windows/amd64"]
+}
+
 ## Groups
 group "linux" {
   targets = [
@@ -174,6 +209,19 @@ group "linux" {
   ]
 }
 
+group "windows" {
+  targets = [
+    "windowsservercore"
+  ]
+}
+
+group "all" {
+  targets = [
+    "linux",
+    "windows",
+  ]
+}
+
 ## Common functions
 # return true if JENKINS_VERSION is a Weekly (one sequence of digits with a trailing literal '.')
 function "is_jenkins_version_weekly" {
@@ -290,6 +338,25 @@ function "linux_tags" {
   )
 }
 
+# Return an array of tags depending on the agent type, the jdk
+# and the flavor and version of Windows passed as parameters (ex: windowsservercore-ltsc2022)
+function "windows_tags" {
+  params = [distribution, jdk]
+  result = [
+    ## Always publish explicit jdk tag
+    tag(true, "jdk${jdk}-hotspot-${distribution}"),
+    tag_weekly(false, "jdk${jdk}-hotspot-${distribution}"),
+    tag_lts(false, "lts-jdk${jdk}-hotspot-${distribution}"),
+
+    # ## Default JDK extra short tags
+    is_default_jdk(jdk) ? tag(true, "hotspot-${distribution}") : "",
+    is_default_jdk(jdk) ? tag_weekly(false, distribution) : "",
+    is_default_jdk(jdk) ? tag_weekly(true, distribution) : "",
+    is_default_jdk(jdk) ? tag_lts(false, "lts-${distribution}") : "",
+    is_default_jdk(jdk) ? tag_lts(true, distribution) : "",
+  ]
+}
+
 # Return if the distribution passed in parameter is Alpine
 function "is_alpine" {
   params = [distribution]
@@ -351,3 +418,13 @@ function "debian_tags" {
     is_default_jdk(jdk) ? tag_lts(true, slim_suffix(variant, "lts")) : "",
   ]
 }
+
+# Return array of Windows version(s) to build
+# Can be overriden by setting WINDOWS_VERSION_OVERRIDE to a specific Windows version
+# Ex: WINDOWS_VERSION_OVERRIDE=ltsc2025 docker buildx bake windows
+function "windowsversions" {
+  params = []
+  result = (notequal(WINDOWS_VERSION_OVERRIDE, "")
+    ? [WINDOWS_VERSION_OVERRIDE]
+    : is_jenkins_version_weekly() ? windows_version_to_build_for_weekly : windows_version_to_build_for_lts)
+}
diff --git a/make.ps1 b/make.ps1
index 81620eabc8..22a8785970 100644
--- a/make.ps1
+++ b/make.ps1
@@ -1,17 +1,25 @@
 [CmdletBinding()]
 Param(
-    [Parameter(Position=1)]
+    [Parameter(Position = 1)]
+    # Default script target
     [String] $Target = 'build',
+    # Jenkins version to include
     [String] $JenkinsVersion = '2.534',
-    [switch] $DryRun = $false
+    # Windows flavor and windows version to build
+    [String] $ImageType = 'windowsservercore-ltsc2022',
+    # Generate a docker compose file even if it already exists
+    [switch] $OverwriteDockerComposeFile = $false,
+    # Print the build and publish command instead of executing them if set
+    [switch] $DryRun = $false,
+    # Output debug info for tests: 'empty' (no additional test output), 'debug' (test cmd & stderr outputed), 'verbose' (test cmd, stderr, stdout outputed)
+    [String] $TestsDebug = ''
 )
 
 $ErrorActionPreference = 'Stop'
 $ProgressPreference = 'SilentlyContinue' # Disable Progress bar for faster downloads
 
 $Repository = 'jenkins'
-$Organisation = 'jenkins4eval'
-$ImageType = 'windowsservercore-ltsc2022' # <WINDOWS_FLAVOR>-<WINDOWS_VERSION>
+$Organisation = 'jenkins'
 
 if(![String]::IsNullOrWhiteSpace($env:DOCKERHUB_REPO)) {
     $Repository = $env:DOCKERHUB_REPO
@@ -32,103 +40,167 @@ if(![String]::IsNullOrWhiteSpace($env:IMAGE_TYPE)) {
 $env:DOCKERHUB_ORGANISATION = "$Organisation"
 $env:DOCKERHUB_REPO = "$Repository"
 $env:JENKINS_VERSION = "$JenkinsVersion"
+$env:COMMIT_SHA = git rev-parse HEAD
 
-# Add 'lts-' prefix to LTS tags not including Jenkins version
-# Compared to weekly releases, LTS releases include an additional build number in their version
-# Note: the ':' separator is included as trying to set an environment variable to empty on Windows unset it.
-$env:SEPARATOR_LTS_PREFIX = ':'
-$releaseLine = 'war'
-if ($JenkinsVersion.Split('.').Count -eq 3) {
-    $env:SEPARATOR_LTS_PREFIX = ':lts-'
-    $releaseLine = 'war-stable'
-}
-
-# If there is no WAR_URL set, using get.jenkins.io URL depending on the release line
-if([String]::IsNullOrWhiteSpace($env:WAR_URL)) {
-    $env:WAR_URL = 'https://get.jenkins.io/{0}/{1}/jenkins.war' -f $releaseLine, $env:JENKINS_VERSION
-}
-
-$items = $ImageType.Split('-')
-$env:WINDOWS_FLAVOR = $items[0]
-$env:WINDOWS_VERSION = $items[1]
-
-# Retrieve the sha256 corresponding to the war file
-$warShaURL = '{0}.sha256' -f $env:WAR_URL
-$webClient = New-Object System.Net.WebClient
-$env:WAR_SHA = $webClient.DownloadString($warShaURL).Split(' ')[0]
-
-$env:COMMIT_SHA=$(git rev-parse HEAD)
-
-$baseDockerCmd = 'docker-compose --file=build-windows.yaml'
-$baseDockerBuildCmd = '{0} build --parallel --pull' -f $baseDockerCmd
-
-Write-Host "= PREPARE: List of $Organisation/$Repository images and tags to be processed:"
-Invoke-Expression "$baseDockerCmd config"
+# Check for required commands
+Function Test-CommandExists {
+    Param (
+        [String] $command
+    )
 
-if($target -eq 'build') {
-    Write-Host '= BUILD: Building all images...'
-    switch ($DryRun) {
-        $true { Write-Host "(dry-run) $baseDockerBuildCmd" }
-        $false { Invoke-Expression $baseDockerBuildCmd }
+    $oldPreference = $ErrorActionPreference
+    $ErrorActionPreference = 'stop'
+    try {
+        # Special case to test "docker buildx"
+        if ($command.Contains(' ')) {
+            Invoke-Expression $command | Out-Null
+            Write-Debug "$command exists"
+        } else {
+            if(Get-Command $command){
+                Write-Debug "$command exists"
+            }
+        }
     }
-    Write-Host '= BUILD: Finished building all images.'
-
-    if($lastExitCode -ne 0 -and !$DryRun) {
-        Write-Error "= BUILD: failed!"
-        exit $lastExitCode
+    Catch {
+        "$command does not exist"
+    }
+    Finally {
+        $ErrorActionPreference = $oldPreference
     }
 }
 
 function Test-Image {
     param (
-        $ImageName
+        [String] $ImageName
     )
 
-    Write-Host "= TEST: Testing image ${ImageName}:"
+    Write-Host "= TEST: Received ${ImageName} image name"
+
+    $items = $ImageName.split(':')
+    $orgRepo = $items[0] -replace 'docker.io/', ''
+    $tag = $items[1]
+
+    Write-Host "= TEST: Testing ${tag} tag of ${orgRepo} repository"
 
-    $env:CONTROLLER_IMAGE = $ImageName
-    $env:DOCKERFILE = 'windows/{0}/hotspot/Dockerfile' -f $env:WINDOWS_FLAVOR
+    $env:DOCKERHUB_ORG_REPO = $orgRepo
+    $env:CONTROLLER_TAG = $tag
 
-    if (Test-Path ".\target\$ImageName") {
-        Remove-Item -Recurse -Force ".\target\$ImageName"
+    $targetPath = '.\target\{0}' -f $tag
+    if (Test-Path $targetPath) {
+        Remove-Item -Recurse -Force $targetPath
     }
-    New-Item -Path ".\target\$ImageName" -Type Directory | Out-Null
-    $configuration.TestResult.OutputPath = ".\target\$ImageName\junit-results.xml"
+    New-Item -Path $targetPath -Type Directory | Out-Null
+    $configuration.TestResult.OutputPath = '{0}\junit-results.xml' -f $targetPath
 
     $TestResults = Invoke-Pester -Configuration $configuration
     $failed = $false
     if ($TestResults.FailedCount -gt 0) {
-        Write-Host "There were $($TestResults.FailedCount) failed tests in $ImageName"
+        Write-Host "There were $($TestResults.FailedCount) failed tests in $tag"
         $failed = $true
     } else {
-        Write-Host "There were $($TestResults.PassedCount) passed tests out of $($TestResults.TotalCount) in $ImageName"
+        Write-Host "There were $($TestResults.PassedCount) passed tests out of $($TestResults.TotalCount) in $tag"
     }
 
-    Remove-Item env:\CONTROLLER_IMAGE
-    Remove-Item env:\DOCKERFILE
+    Remove-Item env:\DOCKERHUB_ORG_REPO
+    Remove-Item env:\CONTROLLER_TAG
 
     return $failed
 }
 
-if($target -eq 'test') {
+function Initialize-DockerComposeFile {
+    param (
+        [String] $ImageType,
+        [String] $DockerComposeFile
+    )
+
+    Write-Host "= PREPARE: Docker compose file generation for $ImageType"
+
+    $items = $ImageType.Split('-')
+    $windowsFlavor = $items[0]
+    $windowsVersion = $items[1]
+
+    # Override the list of Windows versions taken defined in docker-bake.hcl by the version from image type
+    $env:WINDOWS_VERSION_OVERRIDE = $windowsVersion
+
+    # Retrieve the targets from docker buildx bake --print output
+    # Remove the 'output' section (unsupported by docker compose)
+    # For each target name as service key, return a map consisting of:
+    # - 'image' set to the first tag value
+    # - 'build' set to the content of the bake target
+    $yqMainQuery = '.target[] | del(.output) | {(. | key): {\"image\": .tags[0], \"build\": .}}'
+    # Encapsulate under a top level 'services' map
+    $yqServicesQuery = '{\"services\": .}'
+
+    # - Use docker buildx bake to output image definitions from the "<windowsFlavor>" bake target
+    # - Convert with yq to the format expected by docker compose
+    # - Store the result in the docker compose file
+    docker buildx bake --progress=plain --file=docker-bake.hcl $windowsFlavor --print |
+        yq --prettyPrint $yqMainQuery |
+        yq $yqServicesQuery |
+        Out-File -FilePath $DockerComposeFile
+
+    # Remove override
+    Remove-Item env:\WINDOWS_VERSION_OVERRIDE
+}
+
+Test-CommandExists 'docker'
+Test-CommandExists 'docker-compose'
+Test-CommandExists 'docker buildx'
+Test-CommandExists 'yq'
+
+# Sanity check
+yq --version
+
+$dockerComposeFile = 'build-windows_{0}.yaml' -f $ImageType
+$baseDockerCmd = 'docker-compose --file={0}' -f $dockerComposeFile
+$baseDockerBuildCmd = '{0} build --parallel --pull' -f $baseDockerCmd
+
+# Generate the docker compose file if it doesn't exists or if the parameter OverwriteDockerComposeFile is set
+if ((Test-Path $dockerComposeFile) -and -not $OverwriteDockerComposeFile) {
+    Write-Host "= PREPARE: The docker compose file '$dockerComposeFile' containing the image definitions already exists."
+} else {
+    Write-Host "= PREPARE: Initialize the docker compose file '$dockerComposeFile' containing the image definitions."
+    Initialize-DockerComposeFile -ImageType $ImageType -DockerComposeFile $dockerComposeFile
+}
+
+Write-Host '= PREPARE: List of images and tags to be processed:'
+Invoke-Expression "$baseDockerCmd config"
+
+if ($target -eq 'build') {
+    Write-Host '= BUILD: Building all images...'
+
+    switch ($DryRun) {
+        $true { Write-Host "(dry-run) $baseDockerBuildCmd" }
+        $false { Invoke-Expression $baseDockerBuildCmd }
+    }
+
+    if ($lastExitCode -ne 0) {
+        exit $lastExitCode
+    }
+
+    Write-Host '= BUILD: Finished building all images.'
+}
+
+if ($target -eq 'test') {
     if ($DryRun) {
-        Write-Host '(dry-run) test'
+        Write-Host '= TEST: (dry-run) test harness skipped'
     } else {
-        # Only fail the run afterwards in case of any test failures
-        $testFailed = $false
+        Write-Host '= TEST: Starting test harness'
+
         $mod = Get-InstalledModule -Name Pester -MinimumVersion 5.3.0 -MaximumVersion 5.3.3 -ErrorAction SilentlyContinue
-        if($null -eq $mod) {
-            $module = 'c:\Program Files\WindowsPowerShell\Modules\Pester'
-            if(Test-Path $module) {
+        if ($null -eq $mod) {
+            Write-Host '= TEST: Pester 5.3.x not found: installing...'
+            $module = 'C:\Program Files\WindowsPowerShell\Modules\Pester'
+            if (Test-Path $module) {
                 takeown /F $module /A /R
                 icacls $module /reset
                 icacls $module /grant Administrators:'F' /inheritance:d /T
                 Remove-Item -Path $module -Recurse -Force -Confirm:$false
             }
-            Install-Module -Force -Name Pester -Verbose -MaximumVersion 5.3.3
+            Install-Module -Force -Name Pester -MaximumVersion 5.3.3
         }
 
-        Import-Module -Verbose Pester
+        Import-Module Pester
         Write-Host '= TEST: Setting up Pester environment...'
         $configuration = [PesterConfiguration]::Default
         $configuration.Run.PassThru = $true
@@ -142,35 +214,36 @@ if($target -eq 'test') {
         Write-Host '= TEST: Testing all images...'
         # Only fail the run afterwards in case of any test failures
         $testFailed = $false
-        Invoke-Expression "$baseDockerCmd config" | yq '.services[].image' | ForEach-Object {
-            $testFailed = $testFailed -or (Test-Image $_.split(':')[1])
+        $imageDefinitions = Invoke-Expression "$baseDockerCmd config" | yq --unwrapScalar --output-format json '.services' | ConvertFrom-Json
+        foreach ($imageDefinition in $imageDefinitions.PSObject.Properties) {
+            $testFailed = $testFailed -or (Test-Image -ImageName $imageDefinition.Value.image)
         }
 
         # Fail if any test failures
-        if($testFailed -ne $false) {
-            Write-Error 'Test stage failed!'
+        if ($testFailed -ne $false) {
+            Write-Error '= TEST: Test stage failed'
             exit 1
         } else {
-            Write-Host 'Test stage passed!'
+            Write-Host '= TEST: Test stage passed!'
         }
     }
 }
 
-if($target -eq "publish") {
-    Write-Host "= PUBLISH: push all images and tags"
+if ($target -eq 'publish') {
+    Write-Host '= PUBLISH: push all images and tags'
     switch($DryRun) {
         $true { Write-Host "(dry-run) $baseDockerCmd push" }
         $false { Invoke-Expression "$baseDockerCmd push" }
     }
 
     # Fail if any issues when publising the docker images
-    if($lastExitCode -ne 0) {
-        Write-Error "= PUBLISH: failed!"
+    if ($lastExitCode -ne 0) {
+        Write-Error '= PUBLISH: failed!'
         exit 1
     }
 }
 
-if($lastExitCode -ne 0 -and !$DryRun) {
+if ($lastExitCode -ne 0 -and !$DryRun) {
     Write-Error 'Build failed!'
 } else {
     Write-Host 'Build finished successfully'
diff --git a/tests/golden/expected_platforms.txt b/tests/golden/expected_platforms.txt
index 9cecd8e103..0512ebc3db 100644
--- a/tests/golden/expected_platforms.txt
+++ b/tests/golden/expected_platforms.txt
@@ -20,3 +20,5 @@ rhel_jdk21:linux/ppc64le
 rhel_jdk25:linux/amd64
 rhel_jdk25:linux/arm64
 rhel_jdk25:linux/ppc64le
+windowsservercore-ltsc2022_jdk21:windows/amd64
+windowsservercore-ltsc2022_jdk25:windows/amd64
diff --git a/tests/golden/expected_tags.txt b/tests/golden/expected_tags.txt
index 555e6bd1c7..22de5c93a4 100644
--- a/tests/golden/expected_tags.txt
+++ b/tests/golden/expected_tags.txt
@@ -2,8 +2,11 @@ docker.io/jenkins/jenkins:2.534 (debian_jdk21)
 docker.io/jenkins/jenkins:2.534-alpine (alpine_jdk21)
 docker.io/jenkins/jenkins:2.534-alpine-jdk21 (alpine_jdk21)
 docker.io/jenkins/jenkins:2.534-alpine-jdk25 (alpine_jdk25)
+docker.io/jenkins/jenkins:2.534-hotspot-windowsservercore-ltsc2022 (windowsservercore-ltsc2022_jdk21)
 docker.io/jenkins/jenkins:2.534-jdk21 (debian_jdk21)
+docker.io/jenkins/jenkins:2.534-jdk21-hotspot-windowsservercore-ltsc2022 (windowsservercore-ltsc2022_jdk21)
 docker.io/jenkins/jenkins:2.534-jdk25 (debian_jdk25)
+docker.io/jenkins/jenkins:2.534-jdk25-hotspot-windowsservercore-ltsc2022 (windowsservercore-ltsc2022_jdk25)
 docker.io/jenkins/jenkins:2.534-rhel-ubi9-jdk21 (rhel_jdk21)
 docker.io/jenkins/jenkins:2.534-rhel-ubi9-jdk25 (rhel_jdk25)
 docker.io/jenkins/jenkins:2.534-slim (debian-slim_jdk21)
diff --git a/tests/golden/expected_tags_latest_lts.txt b/tests/golden/expected_tags_latest_lts.txt
index 21a0359c96..f8865561ef 100644
--- a/tests/golden/expected_tags_latest_lts.txt
+++ b/tests/golden/expected_tags_latest_lts.txt
@@ -3,9 +3,13 @@ docker.io/jenkins/jenkins:2.504.3-alpine (alpine_jdk21)
 docker.io/jenkins/jenkins:2.504.3-alpine-jdk17 (alpine_jdk17)
 docker.io/jenkins/jenkins:2.504.3-alpine-jdk21 (alpine_jdk21)
 docker.io/jenkins/jenkins:2.504.3-alpine-jdk25 (alpine_jdk25)
+docker.io/jenkins/jenkins:2.504.3-hotspot-windowsservercore-ltsc2019 (windowsservercore-ltsc2019_jdk21)
 docker.io/jenkins/jenkins:2.504.3-jdk17 (debian_jdk17)
+docker.io/jenkins/jenkins:2.504.3-jdk17-hotspot-windowsservercore-ltsc2019 (windowsservercore-ltsc2019_jdk17)
 docker.io/jenkins/jenkins:2.504.3-jdk21 (debian_jdk21)
+docker.io/jenkins/jenkins:2.504.3-jdk21-hotspot-windowsservercore-ltsc2019 (windowsservercore-ltsc2019_jdk21)
 docker.io/jenkins/jenkins:2.504.3-jdk25 (debian_jdk25)
+docker.io/jenkins/jenkins:2.504.3-jdk25-hotspot-windowsservercore-ltsc2019 (windowsservercore-ltsc2019_jdk25)
 docker.io/jenkins/jenkins:2.504.3-lts (debian_jdk21)
 docker.io/jenkins/jenkins:2.504.3-lts-alpine (alpine_jdk21)
 docker.io/jenkins/jenkins:2.504.3-lts-jdk17 (debian_jdk17)
@@ -22,14 +26,18 @@ docker.io/jenkins/jenkins:2.504.3-slim (debian-slim_jdk21)
 docker.io/jenkins/jenkins:2.504.3-slim-jdk17 (debian-slim_jdk17)
 docker.io/jenkins/jenkins:2.504.3-slim-jdk21 (debian-slim_jdk21)
 docker.io/jenkins/jenkins:2.504.3-slim-jdk25 (debian-slim_jdk25)
+docker.io/jenkins/jenkins:2.504.3-windowsservercore-ltsc2019 (windowsservercore-ltsc2019_jdk21)
 docker.io/jenkins/jenkins:lts (debian_jdk21)
 docker.io/jenkins/jenkins:lts-alpine (alpine_jdk21)
 docker.io/jenkins/jenkins:lts-alpine-jdk17 (alpine_jdk17)
 docker.io/jenkins/jenkins:lts-alpine-jdk21 (alpine_jdk21)
 docker.io/jenkins/jenkins:lts-alpine-jdk25 (alpine_jdk25)
 docker.io/jenkins/jenkins:lts-jdk17 (debian_jdk17)
+docker.io/jenkins/jenkins:lts-jdk17-hotspot-windowsservercore-ltsc2019 (windowsservercore-ltsc2019_jdk17)
 docker.io/jenkins/jenkins:lts-jdk21 (debian_jdk21)
+docker.io/jenkins/jenkins:lts-jdk21-hotspot-windowsservercore-ltsc2019 (windowsservercore-ltsc2019_jdk21)
 docker.io/jenkins/jenkins:lts-jdk25 (debian_jdk25)
+docker.io/jenkins/jenkins:lts-jdk25-hotspot-windowsservercore-ltsc2019 (windowsservercore-ltsc2019_jdk25)
 docker.io/jenkins/jenkins:lts-rhel-ubi9-jdk17 (rhel_jdk17)
 docker.io/jenkins/jenkins:lts-rhel-ubi9-jdk21 (rhel_jdk21)
 docker.io/jenkins/jenkins:lts-rhel-ubi9-jdk25 (rhel_jdk25)
@@ -37,3 +45,4 @@ docker.io/jenkins/jenkins:lts-slim (debian-slim_jdk21)
 docker.io/jenkins/jenkins:lts-slim-jdk17 (debian-slim_jdk17)
 docker.io/jenkins/jenkins:lts-slim-jdk21 (debian-slim_jdk21)
 docker.io/jenkins/jenkins:lts-slim-jdk25 (debian-slim_jdk25)
+docker.io/jenkins/jenkins:lts-windowsservercore-ltsc2019 (windowsservercore-ltsc2019_jdk21)
diff --git a/tests/golden/expected_tags_latest_weekly.txt b/tests/golden/expected_tags_latest_weekly.txt
index 22538ab512..ec0e509ea4 100644
--- a/tests/golden/expected_tags_latest_weekly.txt
+++ b/tests/golden/expected_tags_latest_weekly.txt
@@ -2,20 +2,26 @@ docker.io/jenkins/jenkins:2.534 (debian_jdk21)
 docker.io/jenkins/jenkins:2.534-alpine (alpine_jdk21)
 docker.io/jenkins/jenkins:2.534-alpine-jdk21 (alpine_jdk21)
 docker.io/jenkins/jenkins:2.534-alpine-jdk25 (alpine_jdk25)
+docker.io/jenkins/jenkins:2.534-hotspot-windowsservercore-ltsc2022 (windowsservercore-ltsc2022_jdk21)
 docker.io/jenkins/jenkins:2.534-jdk21 (debian_jdk21)
+docker.io/jenkins/jenkins:2.534-jdk21-hotspot-windowsservercore-ltsc2022 (windowsservercore-ltsc2022_jdk21)
 docker.io/jenkins/jenkins:2.534-jdk25 (debian_jdk25)
+docker.io/jenkins/jenkins:2.534-jdk25-hotspot-windowsservercore-ltsc2022 (windowsservercore-ltsc2022_jdk25)
 docker.io/jenkins/jenkins:2.534-rhel-ubi9-jdk21 (rhel_jdk21)
 docker.io/jenkins/jenkins:2.534-rhel-ubi9-jdk25 (rhel_jdk25)
 docker.io/jenkins/jenkins:2.534-slim (debian-slim_jdk21)
 docker.io/jenkins/jenkins:2.534-slim-jdk21 (debian-slim_jdk21)
 docker.io/jenkins/jenkins:2.534-slim-jdk25 (debian-slim_jdk25)
+docker.io/jenkins/jenkins:2.534-windowsservercore-ltsc2022 (windowsservercore-ltsc2022_jdk21)
 docker.io/jenkins/jenkins:alpine (alpine_jdk21)
 docker.io/jenkins/jenkins:alpine-jdk21 (alpine_jdk21)
 docker.io/jenkins/jenkins:alpine-jdk25 (alpine_jdk25)
 docker.io/jenkins/jenkins:alpine3.23-jdk21 (alpine_jdk21)
 docker.io/jenkins/jenkins:alpine3.23-jdk25 (alpine_jdk25)
 docker.io/jenkins/jenkins:jdk21 (debian_jdk21)
+docker.io/jenkins/jenkins:jdk21-hotspot-windowsservercore-ltsc2022 (windowsservercore-ltsc2022_jdk21)
 docker.io/jenkins/jenkins:jdk25 (debian_jdk25)
+docker.io/jenkins/jenkins:jdk25-hotspot-windowsservercore-ltsc2022 (windowsservercore-ltsc2022_jdk25)
 docker.io/jenkins/jenkins:latest (debian_jdk21)
 docker.io/jenkins/jenkins:latest-jdk21 (debian_jdk21)
 docker.io/jenkins/jenkins:latest-jdk25 (debian_jdk25)
@@ -24,3 +30,4 @@ docker.io/jenkins/jenkins:rhel-ubi9-jdk25 (rhel_jdk25)
 docker.io/jenkins/jenkins:slim (debian-slim_jdk21)
 docker.io/jenkins/jenkins:slim-jdk21 (debian-slim_jdk21)
 docker.io/jenkins/jenkins:slim-jdk25 (debian-slim_jdk25)
+docker.io/jenkins/jenkins:windowsservercore-ltsc2022 (windowsservercore-ltsc2022_jdk21)
diff --git a/tests/jenkinsfile.bats b/tests/jenkinsfile.bats
index 963f06d4fc..a25578adff 100644
--- a/tests/jenkinsfile.bats
+++ b/tests/jenkinsfile.bats
@@ -6,6 +6,6 @@ load test_helpers
 
 SUT_DESCRIPTION="Jenkinsfile"
 
-@test "[${SUT_DESCRIPTION}] Default (weekly) targets from docker bake are taken in account in Jenkinsfile" {
-  [ "$(get_default_docker_bake_targets)" == "$(get_targets_from_jenkinsfile)" ]
+@test "[${SUT_DESCRIPTION}] Default (weekly) Linux targets from docker bake are taken in account in Jenkinsfile" {
+  [ "$(get_default_docker_bake_linux_targets)" == "$(get_targets_from_jenkinsfile)" ]
 }
diff --git a/tests/test_helpers.bash b/tests/test_helpers.bash
index 195d669f45..70bcd457f7 100644
--- a/tests/test_helpers.bash
+++ b/tests/test_helpers.bash
@@ -122,8 +122,8 @@ function get_targets_from_jenkinsfile {
      | sort `# ensure constant output sort`
 }
 
-function get_default_docker_bake_targets {
-    make --silent show | jq -r '.target | keys[]' | sort
+function get_default_docker_bake_linux_targets {
+    make --silent show-linux | jq -r '.target | keys[]' | sort
 }
 
 function test_url {
diff --git a/tests/test_helpers.psm1 b/tests/test_helpers.psm1
index 9e89f1fb7b..17bc0e3544 100644
--- a/tests/test_helpers.psm1
+++ b/tests/test_helpers.psm1
@@ -66,8 +66,9 @@ function Retry-Command {
 }
 
 function Get-SutImage {
-    $DOCKERFILE = Get-EnvOrDefault 'DOCKERFILE' ''
-    $IMAGENAME = Get-EnvOrDefault 'CONTROLLER_IMAGE' '' # Ex: jdk17-hotspot-windowsservercore-ltsc2022
+    # TODO: don't hardcode Windows flavor
+    $DOCKERFILE = 'windows/windowsservercore/hotspot/Dockerfile'
+    $IMAGETAG = Get-EnvOrDefault 'CONTROLLER_TAG' ''
 
     $REAL_DOCKERFILE=Resolve-Path -Path "$PSScriptRoot/../${DOCKERFILE}"
 
@@ -76,7 +77,7 @@ function Get-SutImage {
         exit 1
     }
 
-    return "pester-jenkins-$IMAGENAME"
+    return "pester-jenkins-$IMAGETAG"
 }
 
 function Run-Program($cmd, $params, $verbose=$false) {
@@ -105,11 +106,16 @@ function Run-Program($cmd, $params, $verbose=$false) {
 }
 
 function Build-Docker($tag) {
-    $exitCode, $stdout, $stderr = Run-Program 'docker-compose' '--file=build-windows.yaml build --parallel'
+    $windowsVersion = '2019'
+    if ($tag -match 'ltsc(\d+)$') {
+        $windowsVersion = $matches[1]
+    }
+    $composeParams = '--file=build-windows_windowsservercore-ltsc{0}.yaml build --parallel' -f $windowsVersion
+    $exitCode, $stdout, $stderr = Run-Program 'docker-compose' $composeParams
     if($exitCode -ne 0) {
         return $exitCode, $stdout, $stderr
     }
-    return(Run-Program 'docker' $('tag {0}/{1}:{2} {3}' -f $env:DOCKERHUB_ORGANISATION, $env:DOCKERHUB_REPO, $env:CONTROLLER_IMAGE, $tag))
+    return(Run-Program 'docker' $('tag {0}:{1} {2}' -f $env:DOCKERHUB_ORG_REPO, $env:CONTROLLER_TAG, $tag))
 }
 
 function Build-DockerChild($tag, $dir) {
diff --git a/updatecli/updatecli.d/jdk21.yaml b/updatecli/updatecli.d/jdk21.yaml
index 9ca71a425e..b44ad5545d 100644
--- a/updatecli/updatecli.d/jdk21.yaml
+++ b/updatecli/updatecli.d/jdk21.yaml
@@ -50,19 +50,6 @@ targets:
       path: variable.JAVA21_VERSION.default
     scmid: default
 
-  setJDK21VersionWindowsDockerCompose:
-    name: "Bump JDK21 version in build-windows.yaml"
-    kind: yaml
-    transformers:
-      - replacer:
-          from: "+"
-          to: "_"
-    spec:
-      files:
-        - build-windows.yaml
-      key: $.services.jdk21.build.args.JAVA_VERSION
-    scmid: default
-
 actions:
   default:
     kind: github/pullrequest
diff --git a/updatecli/updatecli.d/jdk25.yaml b/updatecli/updatecli.d/jdk25.yaml
index ff428bb026..450dc4c4a9 100644
--- a/updatecli/updatecli.d/jdk25.yaml
+++ b/updatecli/updatecli.d/jdk25.yaml
@@ -50,19 +50,6 @@ targets:
       path: variable.JAVA25_VERSION.default
     scmid: default
 
-  setJDK25VersionWindowsDockerCompose:
-    name: "Bump JDK25 version in build-windows.yaml"
-    kind: yaml
-    transformers:
-      - replacer:
-          from: "+"
-          to: "_"
-    spec:
-      files:
-        - build-windows.yaml
-      key: $.services.jdk25.build.args.JAVA_VERSION
-    scmid: default
-
 actions:
   default:
     kind: github/pullrequest