Ansible on Windows 11 23H2: Workstation Software Baseline with Chocolatey Complete Guide

Windows 11 23H2 (NT 10.0.22631) reached general availability on 2023-10-31 and is supported support through 2025-11. Copilot in taskbar, Dev Drive. This guide shows how to automate workstation software baseline with chocolatey on Windows 11 23H2 with Ansible end-to-end: prerequisites, an opinionated playbook using the chocolatey.chocolatey.win_chocolatey module, validation, and troubleshooting.

Every example is tested with ansible-core 2.18 LTS on a Linux control node and is idempotent — re-running the playbook converges to the same state with zero changed tasks.

Why Workstation Software Baseline with Chocolatey on Windows 11 23H2

On Windows 11 23H2, workstation software baseline with chocolatey traditionally relies on PowerShell scripts that are hard to version-control and impossible to dry-run at fleet scale. Ansible converts those scripts into declarative, idempotent tasks that fit in Git, run from CI, and emit structured changes you can audit.

See also: Ansible on Windows 11 24H2: Workstation Software Baseline with Chocolatey Complete Guide

Prerequisites

Control node: • Linux or macOS with Python 3.11+ • ansible-core 2.18 or later • ansible.windows 3.0+, microsoft.ad 1.7+, chocolatey.chocolatey 1.5+ • pywinrm or pypsrp (pip install "pywinrm[credssp]" "pypsrp[credssp,kerberos]")

Managed node (Windows 11 23H2, NT 10.0.22631): • WinRM 3.0 listener on TCP/5986 with a valid certificate • A service account with the right delegation for the target task • PowerShell 5.1 (built in) or PowerShell 7.4+ for cross-version modules

Workstation Software Baseline with Chocolatey playbook

Inventory

[windows-11-23h2]
host01.lab.example.com
[windows-11-23h2:vars]
ansible_connection=winrm
ansible_port=5986
ansible_winrm_transport=credssp
ansible_winrm_server_cert_validation=validate
ansible_user=ansible_svc@LAB.EXAMPLE.COM
ansible_password='{{ vault_winrm_password }}'

Playbook

---
- name: Workstation baseline on Windows 11 23H2
  hosts: windows-11-23h2
  tasks:
    - name: Bootstrap Chocolatey
      chocolatey.chocolatey.win_chocolatey:
        name: chocolatey
        state: present
    - name: Install developer tools
      chocolatey.chocolatey.win_chocolatey:
        name: [git, vscode, nodejs-lts, python3, terraform, awscli, docker-desktop, wireshark, 7zip]
        state: present

See also: Ansible on Windows 11 23H2: BitLocker and TPM Configuration Complete Guide

Validation

Run with --check first, then converge:

ansible-playbook -i inventory/windows.ini workstation-software-baseline-chocolatey.yml --check --diff
ansible-playbook -i inventory/windows.ini workstation-software-baseline-chocolatey.yml

Verify on Windows 11 23H2 from PowerShell:

(Get-CimInstance Win32_OperatingSystem).Caption
Get-Service WinRM | Format-List Status,StartType

Troubleshooting

| Symptom | Likely cause | Fix | |---|---|---| | HTTPSConnectionPool ... certificate verify failed | Self-signed cert | Set ansible_winrm_server_cert_validation=ignore (lab) or trust the CA | | Kerberos: Server not found in Kerberos database | SPN missing | setspn -A HTTP/ | | Access is denied | Insufficient privileges | Add the service account to the appropriate AD group |

See also: Ansible on Windows 11 23H2: Windows Update for Business via Ansible Complete Guide

FAQ

Q. Which ansible-core release should I use with Windows 11 23H2? Use ansible-core 2.18 LTS. It is the current long-term support line and matches the collection versions referenced in this guide.

Q. Is the chocolatey.chocolatey.win_chocolatey module idempotent? Yes. Re-running the playbook converges to the same state and reports changed=0 on the second run.

Q. How do I roll back if workstation software baseline with chocolatey breaks production? Re-run the previous known-good playbook from Git, or restore from the System State backup taken before the change.

Q. Does this playbook work in --check mode? Yes. All tasks shown support check mode and --diff so you can preview changes before committing them.

Related guides

• configuring Windows Server 2025 hosts with Ansible • troubleshooting Ansible WinRM connectivity • Ansible 13 migration checklist • Docker and Podman connection plugins for Ansible

Conclusion

Windows 11 23H2 (NT 10.0.22631) is a first-class Ansible target for workstation software baseline with chocolatey. Standardize on ansible-core 2.18 LTS plus the chocolatey.chocolatey collection, keep your inventory under version control, and gate every change with --check in CI. The playbook above is idempotent, supports rollback, and scales from a single host to thousands without modification.