diff --git a/Jenkinsfile b/Jenkinsfile
index 92e0387b..d9e5d04f 100644
--- a/Jenkinsfile
+++ b/Jenkinsfile
@@ -3,103 +3,83 @@ pipeline {
 
     options {
         buildDiscarder(logRotator(daysToKeepStr: '10'))
-        timestamps()
     }
 
     stages {
-        stage('Build') {
-            parallel {
-                stage('Windows') {
-                    agent {
-                        label "docker-windows"
+        stage('docker-inbound-agent') {
+            failFast true
+            matrix {
+                axes {
+                    axis {
+                        name 'AGENT_TYPE'
+                        values 'linux', 'windows-2019'
                     }
-                    options {
-                        timeout(time: 60, unit: 'MINUTES')
-                    }
-                    environment {
-                        DOCKERHUB_ORGANISATION = "${infra.isTrusted() ? 'jenkins' : 'jenkins4eval'}"
-                    }
-                    stages {
-                        stage('Build and Test') {
-                            // This stage is the "CI" and should be run on all code changes triggered by a code change
-                            when {
-                                not { buildingTag() }
-                            }
-                            steps {
-                                powershell '& ./build.ps1 test'
-                            }
-                            post {
-                                always {
-                                    junit(allowEmptyResults: true, keepLongStdio: true, testResults: 'target/**/junit-results.xml')
-                                }
-                            }
+                }
+                stages {
+                    stage('Main') {
+                        agent {
+                            label env.AGENT_TYPE
                         }
-                        stage('Deploy to DockerHub') {
-                            // This stage is the "CD" and should only be run when a tag triggered the build
-                            when {
-                                buildingTag()
-                            }
-                            steps {
-                                script {
-                                    infra.withDockerCredentials {
-                                        // TODO: check if this function has the same beahvior in build.ps1 vs make.ps1
-                                        powershell '& ./build.ps1 -PushVersions -VersionTag $env:TAG_NAME publish'
-                                    }
-                                }
-                            }
+                        options {
+                            timeout(time: 30, unit: 'MINUTES')
                         }
-                    }
-                }
-                stage('Linux') {
-                    agent {
-                        label "docker&&linux"
-                    }
-                    options {
-                        timeout(time: 30, unit: 'MINUTES')
-                    }
-                    environment {
-                        JENKINS_REPO = "${infra.isTrusted() ? 'jenkins' : 'jenkins4eval'}/inbound-agent"
-                    }
-                    stages {
-                        stage('Prepare Docker') {
-                            steps {
-                                sh '''
-                                docker buildx create --use
-                                docker run --rm --privileged multiarch/qemu-user-static --reset -p yes
-                                '''
-                            }
+                        environment {
+                            DOCKERHUB_ORGANISATION = "${infra.isTrusted() ? 'jenkins' : 'jenkins4eval'}"
                         }
-                        stage('Build and Test') {
-                            // This stage is the "CI" and should be run on all code changes triggered by a code change
-                            when {
-                                not { buildingTag() }
-                            }
-                            steps {
-                                sh 'make build'
-                                sh 'make test'
-                                // If the tests are passing for Linux AMD64, then we can build all the CPU architectures
-                                sh 'docker buildx bake --file docker-bake.hcl linux'
-                            }
-                            post {
-                                always {
-                                    junit(allowEmptyResults: true, keepLongStdio: true, testResults: 'target/*.xml')
+                        stages {
+                            stage('Prepare Docker') {
+                                when {
+                                    environment name: 'AGENT_TYPE', value: 'linux'
+                                }
+                                steps {
+                                    sh '''
+                                    docker buildx create --use
+                                    docker run --rm --privileged multiarch/qemu-user-static --reset -p yes
+                                    '''
                                 }
                             }
-                        }
-                        stage('Deploy to DockerHub') {
-                            // This stage is the "CD" and should only be run when a tag triggered the build
-                            when {
-                                buildingTag()
+                            stage('Build and Test') {
+                                // This stage is the "CI" and should be run on all code changes triggered by a code change
+                                when {
+                                    not { buildingTag() }
+                                }
+                                steps {
+                                    script {
+                                        if(isUnix()) {
+                                            sh 'make build'
+                                            sh 'make test'
+                                            // If the tests are passing for Linux AMD64, then we can build all the CPU architectures
+                                            sh 'docker buildx bake --file docker-bake.hcl linux'
+                                        } else {
+                                            powershell "& ./build.ps1 test"
+                                        }
+                                    }
+                                }
+                                post {
+                                    always {
+                                        junit(allowEmptyResults: true, keepLongStdio: true, testResults: 'target/**/junit-results.xml')
+                                    }
+                                }
                             }
-                            steps {
-                                script {
-                                    // This function is defined in the jenkins-infra/pipeline-library
-                                    infra.withDockerCredentials {
-                                        sh '''
-                                        export IMAGE_TAG="${TAG_NAME}"
-                                        export ON_TAG=true
-                                        docker buildx bake --push --file docker-bake.hcl linux
-                                        '''
+                            stage('Deploy to DockerHub') {
+                                // This stage is the "CD" and should only be run when a tag triggered the build
+                                when {
+                                    buildingTag()
+                                }
+                                steps {
+                                    script {
+                                        infra.withDockerCredentials {
+                                            if (isUnix()) {
+                                                sh '''
+                                                export IMAGE_TAG="${TAG_NAME}"
+                                                export ON_TAG=true
+                                                docker buildx bake --push --file docker-bake.hcl linux
+                                                '''
+                                            } else {
+                                                // TODO: check if this function has the same beahvior in build.ps1 vs make.ps1
+                                                powershell "& ./build.ps1 -PushVersions -VersionTag $env:TAG_NAME publish"
+                                            }
+                                        }
                                     }
                                 }
                             }
diff --git a/build-windows.yaml b/build-windows.yaml
index 7febdfa5..a84aef9f 100644
--- a/build-windows.yaml
+++ b/build-windows.yaml
@@ -1,29 +1,33 @@
 services:
-  jdk11-nanoserver-1809:
-    image: jdk11-nanoserver-1809
+  jdk11-nanoserver:
+    image: jdk11-nanoserver-${NANOSERVER_VERSION_NAME}
     build:
       context: ./windows/
       dockerfile: Dockerfile.nanoserver
       args:
         VERSION: ${DOCKER_AGENT_VERSION}
-  jdk17-nanoserver-1809:
-    image: jdk17-nanoserver-1809
+        WINDOWS_VERSION_TAG: ${NANOSERVER_VERSION_TAG}
+  jdk17-nanoserver:
+    image: jdk17-nanoserver-${NANOSERVER_VERSION_NAME}
     build:
       context: ./windows/
       dockerfile: Dockerfile.nanoserver
       args:
         VERSION: ${DOCKER_AGENT_VERSION}
-  jdk11-windowsservercore-ltsc2019:
-    image: jdk11-windowsservercore-ltsc2019
+        WINDOWS_VERSION_TAG: ${NANOSERVER_VERSION_TAG}
+  jdk11-windowsservercore:
+    image: jdk11-windowsservercore-${WINDOWS_VERSION_NAME}
     build:
       context: ./windows/
       dockerfile: Dockerfile.windowsservercore
       args:
         VERSION: ${DOCKER_AGENT_VERSION}
-  jdk17-windowsservercore-ltsc2019:
-    image: jdk17-windowsservercore-ltsc2019
+        WINDOWS_VERSION_TAG: ${WINDOWS_VERSION_TAG}
+  jdk17-windowsservercore:
+    image: jdk17-windowsservercore-${WINDOWS_VERSION_NAME}
     build:
       context: ./windows/
       dockerfile: Dockerfile.windowsservercore
       args:
         VERSION: ${DOCKER_AGENT_VERSION}
+        WINDOWS_VERSION_TAG: ${WINDOWS_VERSION_TAG}
diff --git a/build.ps1 b/build.ps1
index 86f8102a..256a5b38 100644
--- a/build.ps1
+++ b/build.ps1
@@ -10,9 +10,10 @@ Param(
     # [switch] $DisableEnvProps = $false
 )
 
-$ErrorActionPreference = "Stop"
+$ErrorActionPreference ='Stop'
 $Repository = 'inbound-agent'
 $Organization = 'jenkins'
+$AgentType = 'windows-2019'
 
 # TODO: not needed? Commented for now, env.props contains DOCKER_AGENT_VERSION in docker-agent
 # if(!$DisableEnvProps) {
@@ -38,6 +39,10 @@ if(![String]::IsNullOrWhiteSpace($env:DOCKER_AGENT_VERSION)) {
     $DockerAgentVersion = $env:DOCKER_AGENT_VERSION
 }
 
+if(![String]::IsNullOrWhiteSpace($env:AGENT_TYPE)) {
+    $AgentType = $env:AGENT_TYPE
+}
+
 # Check for required commands
 Function Test-CommandExists {
     # From https://devblogs.microsoft.com/scripting/use-a-powershell-function-to-see-if-a-command-exists/
@@ -64,6 +69,15 @@ Function Test-CommandExists {
 $defaultJdk = '11'
 $builds = @{}
 $env:DOCKER_AGENT_VERSION = "$DockerAgentVersion"
+$env:WINDOWS_VERSION_NAME = $AgentType.replace('windows-', 'ltsc')
+$env:NANOSERVER_VERSION_NAME = $env:WINDOWS_VERSION_NAME
+$env:WINDOWS_VERSION_TAG = $env:WINDOWS_VERSION_NAME
+$env:NANOSERVER_VERSION_TAG = $env:WINDOWS_VERSION_NAME
+# We need to keep the `jdkN-nanoserver-1809` images for now, cf https://github.com/jenkinsci/docker-agent/issues/451
+if ($AgentType -eq 'windows-2019') {
+    $env:NANOSERVER_VERSION_TAG = 1809
+    $env:NANOSERVER_VERSION_NAME = 1809
+}
 $ProgressPreference = 'SilentlyContinue' # Disable Progress bar for faster downloads
 
 Test-CommandExists "docker"
@@ -74,7 +88,9 @@ $baseDockerCmd = 'docker-compose --file=build-windows.yaml'
 $baseDockerBuildCmd = '{0} build --parallel --pull' -f $baseDockerCmd
 
 Invoke-Expression "$baseDockerCmd config --services" 2>$null | ForEach-Object {
-    $image = $_
+    $image = '{0}-{1}' -f $_, $env:WINDOWS_VERSION_NAME
+    # Special case for nanoserver-1809 images
+    $image = $image.replace('nanoserver-ltsc2019', 'nanoserver-1809')
     $items = $image.Split("-")
     # Remove the 'jdk' prefix (3 first characters)
     $jdkMajorVersion = $items[0].Remove(0,3)
@@ -119,7 +135,8 @@ function Test-Image {
     Write-Host "= TEST: Testing image ${ImageName}:"
 
     $env:AGENT_IMAGE = $ImageName
-    $env:IMAGE_FOLDER = Invoke-Expression "$baseDockerCmd config" 2>$null |  yq -r ".services.${ImageName}.build.context"
+    $serviceName = $ImageName.SubString(0, $ImageName.LastIndexOf('-'))
+    $env:IMAGE_FOLDER = Invoke-Expression "$baseDockerCmd config" 2>$null |  yq -r ".services.${serviceName}.build.context"
     # TODO: review build number removal (?)
     # $env:VERSION = "$DockerAgentVersion-$BuildNumber"
     $env:VERSION = $DockerAgentVersion
@@ -175,6 +192,7 @@ if($target -eq "test") {
     if(![System.String]::IsNullOrWhiteSpace($Build) -and $builds.ContainsKey($Build)) {
         Test-Image $Build
     } else {
+        Write-Host "= TEST: Testing all images"
         foreach($image in $builds.Keys) {
             Test-Image $image
         }
diff --git a/tests/inboundAgent.Tests.ps1 b/tests/inboundAgent.Tests.ps1
index dd94bb32..b81695ce 100644
--- a/tests/inboundAgent.Tests.ps1
+++ b/tests/inboundAgent.Tests.ps1
@@ -3,6 +3,7 @@ Import-Module -DisableNameChecking -Force $PSScriptRoot/test_helpers.psm1
 $global:AGENT_IMAGE = Get-EnvOrDefault 'AGENT_IMAGE' ''
 $global:IMAGE_FOLDER = Get-EnvOrDefault 'IMAGE_FOLDER' ''
 $global:VERSION = Get-EnvOrDefault 'VERSION' ''
+$global:WINDOWS_VERSION_TAG = Get-EnvOrDefault 'WINDOWS_VERSION_TAG' ''
 
 # TODO: make this name unique for concurency
 $global:CONTAINERNAME = 'pester-jenkins-inbound-agent-{0}' -f $global:AGENT_IMAGE
@@ -20,6 +21,10 @@ $global:WINDOWSVERSION = $items[2]
 $global:CONTAINERSHELL="powershell.exe"
 if($global:WINDOWSFLAVOR -eq 'nanoserver') {
     $global:CONTAINERSHELL = "pwsh.exe"
+    # Special case for nanoserver-1809
+    if($global:WINDOWSVERSION -eq '1809') {
+        $global:WINDOWS_VERSION_TAG = '1809'
+    }
 }
 
 
@@ -31,7 +36,7 @@ BuildNcatImage
 
 Describe "[$global:AGENT_IMAGE] build image" {
     It 'builds image' {
-        $exitCode, $stdout, $stderr = Run-Program 'docker' "build --build-arg VERSION=${global:VERSION} --build-arg JAVA_MAJOR_VERSION=${global:JAVA_MAJOR_VERSION} --tag=${global:AGENT_IMAGE} --file ${global:IMAGE_FOLDER}/Dockerfile.${global:WINDOWSFLAVOR} ${global:IMAGE_FOLDER}"
+        $exitCode, $stdout, $stderr = Run-Program 'docker' "build --build-arg VERSION=${global:VERSION} --build-arg `"WINDOWS_VERSION_TAG=${global:WINDOWS_VERSION_TAG}`" --build-arg JAVA_MAJOR_VERSION=${global:JAVA_MAJOR_VERSION} --tag=${global:AGENT_IMAGE} --file ${global:IMAGE_FOLDER}/Dockerfile.${global:WINDOWSFLAVOR} ${global:IMAGE_FOLDER}"
         $exitCode | Should -Be 0
     }
 }
@@ -122,7 +127,7 @@ Describe "[$global:AGENT_IMAGE] custom build args" {
     }
 
     It 'builds image with arguments' {
-        $exitCode, $stdout, $stderr = Run-Program 'docker' "build --build-arg VERSION=${ARG_TEST_VERSION} --build-arg JAVA_MAJOR_VERSION=${global:JAVA_MAJOR_VERSION} --tag=${customImageName} --file=${global:IMAGE_FOLDER}/Dockerfile.${global:WINDOWSFLAVOR} ${global:IMAGE_FOLDER}"
+        $exitCode, $stdout, $stderr = Run-Program 'docker' "build --build-arg VERSION=${ARG_TEST_VERSION} --build-arg `"WINDOWS_VERSION_TAG=${global:WINDOWS_VERSION_TAG}`" --build-arg JAVA_MAJOR_VERSION=${global:JAVA_MAJOR_VERSION} --tag=${customImageName} --file=${global:IMAGE_FOLDER}/Dockerfile.${global:WINDOWSFLAVOR} ${global:IMAGE_FOLDER}"
         $exitCode | Should -Be 0
 
         $exitCode, $stdout, $stderr = Run-Program 'docker' "run --detach --tty --name $global:CONTAINERNAME $customImageName -Cmd $global:CONTAINERSHELL"
diff --git a/updatecli/updatecli.d/docker-agent.yaml b/updatecli/updatecli.d/docker-agent.yaml
index f0fe347b..7a12a433 100644
--- a/updatecli/updatecli.d/docker-agent.yaml
+++ b/updatecli/updatecli.d/docker-agent.yaml
@@ -100,8 +100,8 @@ conditions:
       tag: '{{source "lastVersion" }}-jdk17-windowsservercore-ltsc2019'
 
 targets:
-  setJdk11AlpineDockerImage:
-    name: Bump the parent image `jenkins/agent` version on JDK11 Alpine
+  setAlpineDockerImage:
+    name: Bump the parent image `jenkins/agent` version on Alpine
     kind: dockerfile
     spec:
       file: linux/Dockerfile.alpine
@@ -109,8 +109,8 @@ targets:
         keyword: ARG
         matcher: version
     scmid: default
-  setJdk11DebianDockerImage:
-    name: Bump the parent image `jenkins/agent` version on JDK11 Debian
+  setDebianDockerImage:
+    name: Bump the parent image `jenkins/agent` version on Debian
     kind: dockerfile
     spec:
       file: linux/Dockerfile.debian
@@ -118,8 +118,8 @@ targets:
         keyword: ARG
         matcher: version
     scmid: default
-  setJdk11WindowsNanoserver1809DockerImage:
-    name: Bump the parent image `jenkins/agent` version on JDK11 Windows Nanoserver 1809
+  setsNanoserverDockerImage:
+    name: Bump the parent image `jenkins/agent` version on Windows Nanoserver
     kind: dockerfile
     spec:
       file: windows/Dockerfile.nanoserver
@@ -127,8 +127,8 @@ targets:
         keyword: ARG
         matcher: version
     scmid: default
-  setJdk11WindowsServer2019DockerImage:
-    name: Bump the parent image `jenkins/agent` version on JDK11 Windows Server 2019
+  setWindowsServerCoreDockerImage:
+    name: Bump the parent image `jenkins/agent` version on Windows Server Core
     kind: dockerfile
     spec:
       file: windows/windowsservercore
@@ -136,42 +136,6 @@ targets:
         keyword: ARG
         matcher: version
     scmid: default
-  setJdk17AlpineDockerImage:
-    name: Bump the parent image `jenkins/agent` version on JDK17 Alpine
-    kind: dockerfile
-    spec:
-      file: linux/Dockerfile.alpine
-      instruction:
-        keyword: ARG
-        matcher: version
-    scmid: default
-  setJdk17DebianDockerImage:
-    name: Bump the parent image `jenkins/agent` version on JDK17 Debian
-    kind: dockerfile
-    spec:
-      file: linux/Dockerfile.debian
-      instruction:
-        keyword: ARG
-        matcher: version
-    scmid: default
-  setJdk17WindowsNanoserver1809DockerImage:
-    name: Bump the parent image `jenkins/agent` version on JDK17 Windows Nanoserver 1809
-    kind: dockerfile
-    spec:
-      file: windows/windowsservercore
-      instruction:
-        keyword: ARG
-        matcher: version
-    scmid: default
-  setJdk17WindowsServer2019DockerImage:
-    name: Bump the parent image `jenkins/agent` version on JDK17 Windows Server 2019
-    kind: dockerfile
-    spec:
-      file: windows/windowsservercore-ltsc2019/Dockerfile
-      instruction:
-        keyword: ARG
-        matcher: version
-    scmid: default
   setDockerBakeDefaultParentImage:
     name: Bump the parent image `jenkins/agent` version on the docker-bake.hcl file
     kind: file
@@ -182,11 +146,11 @@ targets:
       replacepattern: >-
         variable${1}"DOCKER_AGENT_VERSION"${2}{${3}${4}${5}default${6}= "{{ source "lastVersion" }}"
     scmid: default
-  setWindowsMakePwshParentImage:
-    name: Bump the parent image `jenkins/agent` version on the windows make.ps1 file
+  setWindowsBuildPwshParentImage:
+    name: Bump the parent image `jenkins/agent` version on the Windows build.ps1 powershell script
     kind: file
     spec:
-      file: make.ps1
+      file: build.ps1
       matchpattern: >-
         \$DockerAgentVersion(.*)=(.*),
       replacepattern: >-
diff --git a/windows/Dockerfile.nanoserver b/windows/Dockerfile.nanoserver
index c0af7bc5..4ccdc4f4 100644
--- a/windows/Dockerfile.nanoserver
+++ b/windows/Dockerfile.nanoserver
@@ -23,7 +23,8 @@
 
 ARG VERSION=3131.vf2b_b_798b_ce99-3
 ARG JAVA_MAJOR_VERSION=17
-FROM jenkins/agent:"${VERSION}"-jdk"${JAVA_MAJOR_VERSION}"-nanoserver-1809
+ARG WINDOWS_VERSION_TAG=1809
+FROM jenkins/agent:"${VERSION}"-jdk"${JAVA_MAJOR_VERSION}"-nanoserver-"${WINDOWS_VERSION_TAG}"
 
 ARG VERSION=3131.vf2b_b_798b_ce99-3
 LABEL Description="This is a base image, which allows connecting Jenkins agents via JNLP protocols on Windows" Vendor="Jenkins Project" Version="$VERSION"
diff --git a/windows/Dockerfile.windowsservercore b/windows/Dockerfile.windowsservercore
index 3e7cfd72..e1a6a076 100644
--- a/windows/Dockerfile.windowsservercore
+++ b/windows/Dockerfile.windowsservercore
@@ -23,7 +23,8 @@
 
 ARG VERSION=3131.vf2b_b_798b_ce99-3
 ARG JAVA_MAJOR_VERSION=17
-FROM jenkins/agent:"${VERSION}"-jdk"${JAVA_MAJOR_VERSION}"-windowsservercore-ltsc2019
+ARG WINDOWS_VERSION_TAG=ltsc2019
+FROM jenkins/agent:"${VERSION}"-jdk"${JAVA_MAJOR_VERSION}"-windowsservercore-"${WINDOWS_VERSION_TAG}"
 
 ARG VERSION=3131.vf2b_b_798b_ce99-3
 LABEL Description="This is a base image, which allows connecting Jenkins agents via JNLP protocols on Windows" Vendor="Jenkins Project" Version="$VERSION"