diff --git a/FAQ.md b/FAQ.md
index b2c552e2ef..6529c738bf 100644
--- a/FAQ.md
+++ b/FAQ.md
@@ -89,6 +89,7 @@ have at the moment:
 | [Centos6](./ansible/docker/Dockerfile.CentOS6) | [`adoptopenjdk/centos6_build_image`](https://hub.docker.com/r/adoptopenjdk/centos6_build_image)| linux/amd64 | [GH Actions](.github/workflows/build.yml) | Yes
 | [Alpine3](./ansible/docker/Dockerfile.Alpine3) | [`adoptopenjdk/alpine3_build_image`](https://hub.docker.com/r/adoptopenjdk/alpine3_build_image) | linux/x64 & linux/arm64 | [Jenkins](https://ci.adoptium.net/job/centos7_docker_image_updater/) | Yes
 | [Ubuntu 20.04 (riscv64 only)](./ansible/docker/Dockerfile.Ubuntu2004-riscv64) | [`adoptopenjdk/ubuntu2004_build_image:linux-riscv64`](https://hub.docker.com/r/adoptopenjdk/ubuntu2004_build_image) | linux/riscv64 | [Jenkins](https://ci.adoptium.net/job/centos7_docker_image_updater/) | Yes
+| [Windows Server 2022](./ansible/docker/Dockerfile.win2022) | n/a - restricted | Windows | No
 
 <details>
 <summary>(*) - Caveats:</summary>
diff --git a/ansible/docker/Dockerfile.win2022 b/ansible/docker/Dockerfile.win2022
new file mode 100644
index 0000000000..94f4b6e628
--- /dev/null
+++ b/ansible/docker/Dockerfile.win2022
@@ -0,0 +1,34 @@
+FROM mcr.microsoft.com/windows/servercore:ltsc2022
+
+# Specify this with --build-arg PW=SomePassword
+ARG PW=T3mp=Passwd
+
+# Set up cygwin with git and ansible as a bootstrap, and add to system default path
+RUN powershell wget -UseBasicParsing https://cygwin.com/setup-x86_64.exe -OutFile setup-x86_64.exe & \
+    setup-x86_64.exe --packages git,ansible --download --local-install --delete-orphans --site https://mirrors.kernel.org/sourceware/cygwin --local-package-dir c:\cygwin_packages --root C:\cygwin64 --wait --quiet-mode & \
+    C:\cygwin64\bin\git config --system core.autocrlf false & \
+    del setup-x86_64.exe & \
+    setx PATH "c:\cygwin64\bin;%PATH%" & \
+    mkdir c:\temp
+
+# Set up WinRM for the ansible connection
+RUN powershell wget -UseBasicParsing https://raw.githubusercontent.com/ansible/ansible/dd4c56e4d68664e4a50292aa19ea61b15c92287c/examples/scripts/ConfigureRemotingForAnsible.ps1 -OutFile ConfigureRemotingForAnsible.ps1 & \
+    PowerShell .\ConfigureRemotingForAnsible.ps1 -CertValidityDays 9999 & \
+    PowerShell .\ConfigureRemotingForAnsible.ps1 -EnableCredSSP & \
+    PowerShell .\ConfigureRemotingForAnsible.ps1 -ForceNewSSLCert & \
+    PowerShell .\ConfigureRemotingForAnsible.ps1 -SkipNetworkProfileCheck
+
+# Set up WinRM user, clone and run the playbook, then delete the user so it's not in any layer
+ENV TERM=dumb
+
+RUN net user ansible %PW% /ADD & net localgroup "Administrators" ansible /ADD & net localgroup "Remote Management Users" ansible /ADD & \
+    C:\cygwin64\bin\git clone https://github.com/sxa/infrastructure -b windows_docker_support c:/infrastructure & \
+    sed -i -e 's/hosts: .*/hosts: localhost/' infrastructure/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/main.yml & \
+    echo localhost ansible_connection=winrm > infrastructure/ansible/hosts & \
+    cd infrastructure\ansible & \
+    C:\cygwin64\bin\python3.7m.exe /usr/bin/ansible-playbook -e git_sha=00000000 -e ansible_user=ansible -e ansible_password=%PW% -i hosts \
+    --skip-tags=adoptopenjdk,reboot,NTP_TIME,MSVS_2013,MSVS_2017,MSVS_2019 playbooks/AdoptOpenJDK_Windows_Playbook/main.yml & \
+    net user ansible /DELETE
+
+ENTRYPOINT ["C:\\Program Files (x86)\\Microsoft Visual Studio\\2022\\BuildTools\\Common7\\Tools\\VsDevCmd.bat", "&&", "powershell.exe", "-NoLogo", "-ExecutionPolicy", "Bypass"]
+USER ContainerUser
diff --git a/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/main.yml b/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/main.yml
index afc10a15c5..60274091d0 100644
--- a/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/main.yml
+++ b/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/main.yml
@@ -22,7 +22,7 @@
 # It can be defined as 'all' or a specific group which the host belongs to.
 # For example, it can be 'all' or 'x86' for when a host is in the group 'x86'.
 - name: Ansible Windows playbook
-  hosts: "{{ Groups | default('build*win*:test*win*') }}"
+  hosts: "{{ Groups | default('localhost:build:test:perf:jck:!*zos*:!*win*:!*aix*') }}"
   gather_facts: yes
   tasks:
     - name: Load Standard Variables
diff --git a/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/roles/Common/tasks/main.yml b/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/roles/Common/tasks/main.yml
index 12461a994a..aa46f9d9a1 100644
--- a/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/roles/Common/tasks/main.yml
+++ b/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/roles/Common/tasks/main.yml
@@ -64,4 +64,4 @@
   win_reboot:
     reboot_timeout: 1800
   when: not (hostname_output.stdout == "")
-  tags: basic_config
+  tags: basic_config, reboot
diff --git a/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/roles/GPG_signature_verification/tasks/main.yml b/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/roles/GPG_signature_verification/tasks/main.yml
index 11e07c75ab..99a8b1d961 100644
--- a/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/roles/GPG_signature_verification/tasks/main.yml
+++ b/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/roles/GPG_signature_verification/tasks/main.yml
@@ -24,7 +24,7 @@
 
 - name: Import GPG Signing Key
   win_shell: |
-    C:/cygwin64/bin/bash.exe -c "gpg --batch --import c:/temp/gpgkey.asc"
+    C:/cygwin64/bin/bash.exe -c "gpg2 --batch --import c:/temp/gpgkey.asc"
   failed_when: false
 
 - name: Re-enable gpgagent
@@ -39,7 +39,7 @@
   win_command: wget -q "{{ signature_link }}" -O sigfile
 
 - name: Verify binary
-  win_shell: C:/cygwin64/bin/bash.exe -c "gpg --verify sigfile {{ file_path }}"
+  win_shell: C:/cygwin64/bin/bash.exe -c "gpg2 --verify sigfile {{ file_path }}"
 
 - name: Remove gnupg directory with Cygwin ( when it didnt exist previously )
   win_shell: C:/cygwin64/bin/bash.exe -c "rm -rf ~/.gnupg"
diff --git a/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/roles/MSVS_2022/tasks/main.yml b/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/roles/MSVS_2022/tasks/main.yml
index 63f63bce49..309943273f 100644
--- a/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/roles/MSVS_2022/tasks/main.yml
+++ b/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/roles/MSVS_2022/tasks/main.yml
@@ -10,7 +10,7 @@
 
 - name: Test if VS 2022 is installed
   win_stat:
-    path: 'C:\Program Files\Microsoft Visual Studio\2022\Community'
+    path: 'C:\Program Files\Microsoft Visual Studio\2022'
   register: vs2022_installed
   tags: adoptopenjdk
 
@@ -95,40 +95,37 @@
 
 - name: Test if VS 2022 is installed(non adopt)
   win_stat:
-    path: 'C:\Program Files\Microsoft Visual Studio\2022\Community'
+    path: 'C:\Program Files\Microsoft Visual Studio\2022'
   register: vs2022_installed
 
 # Download & Install VS2022 When No Layout & Not AdoptOpenJDK
 # This is the target that you're redirected to when you go to https://aka.ms/vs/17/release/vs_community.exe
 - name: Download Visual Studio Community 2022
   win_get_url:
-    url: 'https://aka.ms/vs/17/release/vs_Community.exe'
-    checksum: 44957c393b3c4dcaf1918f086437a520fc3b3dee83dbe786e5d757f331257856
+# https://learn.microsoft.com/en-us/visualstudio/releases/2022/release-history
+# 17.7.34302.85    url: 'https://download.visualstudio.microsoft.com/download/pr/47b236ad-5505-4752-9d2b-5cf9795528bc/87684889f46dec53d1452f4a0ff9fec1ac202a97ebed866718d7c0269e814b28/vs_BuildTools.exe'
+    url: 'https://download.visualstudio.microsoft.com/download/pr/1d66edfe-3c83-476b-bf05-e8901c62ba7f/bac71effb5a23d7cd1a81e5f628a0c8dcb7e8a07e0aa7077c853ed84a862dceb/vs_BuildTools.exe' # 17.7.3 = 17.7.34024.191
+    checksum: bac71effb5a23d7cd1a81e5f628a0c8dcb7e8a07e0aa7077c853ed84a862dceb
     checksum_algorithm: sha256
-    dest: 'C:\temp\vs_community22.exe'
+    dest: 'C:\temp\vs_BuildTools22.exe'
     force: no
   when: (not vs2022_installed.stat.exists) and (windows_version.stdout_lines[0] | regex_search('^(10\.|11\.|2016|2019|2022)'))
 
 - name: Run Visual Studio 2022 Installer From Download
   win_shell: |
-      Start-Process -Wait -FilePath 'C:\temp\vs_community22.exe' -ArgumentList '--wait --add Microsoft.VisualStudio.Workload.NativeDesktop --includeRecommended --includeOptional --quiet --norestart'
+      Start-Process -Wait -FilePath 'C:\temp\vs_BuildTools22.exe' -ArgumentList '--wait --add Microsoft.VisualStudio.Component.VC.Tools.x86.x64 --add Microsoft.VisualStudio.Workload.NativeDesktop --add Microsoft.VisualStudio.Component.VC.Tools.ARM64 --add Microsoft.VisualStudio.Component.VC.ATL.ARM64 --add Microsoft.VisualStudio.Component.VC.MFC.ARM64 --includeRecommended --includeOptional --quiet --norestart'
   args:
     executable: powershell
   when: (not vs2022_installed.stat.exists) and (windows_version.stdout_lines[0] | regex_search('^(10\.|11\.|2016|2019|2022)'))
   register: vs2022_error
   failed_when: vs2022_error.rc != 0 and vs2022_error.rc != 3010
 
-- name: Install ARM64 components
-  win_shell: Start-Process -FilePath 'C:\temp\vs_community22.exe' -Wait -NoNewWindow -ArgumentList
-    'modify --installPath "C:\Program Files (x86)\Microsoft Visual Studio\2022\Community" --quiet
-    --add Microsoft.VisualStudio.Component.VC.Tools.ARM64 --add Microsoft.VisualStudio.Component.VC.ATL.ARM64 --add Microsoft.VisualStudio.Component.VC.MFC.ARM64'
-  when: (not vs2022_installed.stat.exists) and (windows_version.stdout_lines[0] | regex_search('^(10\.|11\.|2016|2019|2022)'))
-
+#  Note: If this does not find the files, then the NativeDesktop component was not installed
 - name: Register Visual Studio Community 2022 DIA SDK shared libraries
   win_command: 'regsvr32 /s "{{ item }}"'
   with_items:
-    - C:\Program Files\Microsoft Visual Studio\2022\Community\DIA SDK\bin\msdia140.dll
-    - C:\Program Files\Microsoft Visual Studio\2022\Community\DIA SDK\bin\amd64\msdia140.dll
+    - C:\Program Files (x86)\Microsoft Visual Studio\2022\BuildTools\DIA SDK\bin\msdia140.dll
+    - C:\Program Files (x86)\Microsoft Visual Studio\2022\BuildTools\DIA SDK\bin\amd64\msdia140.dll
   when: (not vs2022_installed.stat.exists) and (windows_version.stdout_lines[0] | regex_search('^(10\.|11\.|2016|2019|2022)'))
 
 - name: Reboot machine after Visual Studio installation
diff --git a/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/roles/WMF_5.1/tasks/main.yml b/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/roles/WMF_5.1/tasks/main.yml
index 9ac9b2c0d2..79afd650e4 100644
--- a/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/roles/WMF_5.1/tasks/main.yml
+++ b/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/roles/WMF_5.1/tasks/main.yml
@@ -35,4 +35,4 @@
   when:
     - (powershell_output.stdout < '5')
     - hotfix_install.reboot_required
-  tags: WMF
+  tags: WMF,reboot
diff --git a/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/roles/cygwin/tasks/main.yml b/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/roles/cygwin/tasks/main.yml
index 443bd11eec..fdde87f728 100644
--- a/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/roles/cygwin/tasks/main.yml
+++ b/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/roles/cygwin/tasks/main.yml
@@ -4,7 +4,7 @@
 ##########
 - name: Test if Cygwin is already installed
   win_stat:
-    path: 'C:\cygwin64'
+    path: 'C:\cygwin64\bin\jq.exe'
   register: cygwin_installed
   tags: cygwin
 
@@ -15,6 +15,8 @@
   when: not cygwin_installed.stat.exists
   tags: cygwin
 
+# If you update this with a new package, modify the "Test
+# if installed" to look for something in the new package
 - name: Install Cygwin
   win_shell: |
     Start-Process -Wait -FilePath 'C:\temp\cygwin.exe' -ArgumentList '--packages autoconf,automake,bsdtar,cmake,cpio,curl,gcc-core,git,gnupg,grep,jq,libtool,make,mingw64-x86_64-gcc-core,perl,rsync,unzip,wget,zip --quiet-mode --download --local-install --delete-orphans --site https://mirrors.kernel.org/sourceware/cygwin/ --local-package-dir C:\cygwin_packages --root C:\cygwin64'
diff --git a/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/roles/logs/tasks/main.yml b/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/roles/logs/tasks/main.yml
index 160fca0c14..9a0adc85a0 100644
--- a/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/roles/logs/tasks/main.yml
+++ b/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/roles/logs/tasks/main.yml
@@ -7,14 +7,13 @@
 
 # This task doesn't actually matter, aslong as it runs and is registered. The timestamp for the registered variable is used
 - name: Dummy task to get timestamp
-  win_command: whoami
+  win_command: cmd /c echo hello
   register: date_output
 
 # Accounts for cases where playbook executor is windows and its executing on localhost
-- name: Get Latest git commit SHA (Windows Localhost)
-  win_command: git rev-parse HEAD
+- name: Get Latest git commit SHA (Windows local container)
+  win_command: C:\cygwin64\bin\git -C C:/infrastructure rev-parse HEAD
   register: git_output
-  delegate_to: localhost
   ignore_errors: yes
   when:
     - git_sha is not defined
diff --git a/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/roles/shortNames/tasks/main.yml b/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/roles/shortNames/tasks/main.yml
index 028463cc4e..a425048cc1 100644
--- a/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/roles/shortNames/tasks/main.yml
+++ b/ansible/playbooks/AdoptOpenJDK_Windows_Playbook/roles/shortNames/tasks/main.yml
@@ -22,8 +22,9 @@
   tags:
     - shortnames
 
-- name: Enable shortnames on drive C:/
-  win_shell: "fsutil 8dot3name set C: 0"
+# Note that using "set C: 0" did not work in containers
+- name: Enable shortnames
+  win_shell: "fsutil 8dot3name set 0"
   when: (not enabled_shortnames.stdout)
   tags:
     - shortnames