Windows task: datadog.dd.agent : Check if remote update is in progress - assumes any output is true.

[richarddziennmi]

When installing the DD agent, the task Check if remote update is in progress runs to see if the datadog-install.exe is running

From: windows_remote_update_check.yml

- name: Check if remote update is in progress
  ansible.windows.win_shell: |
    Get-CimInstance Win32_Process | Where-Object {
        $_.Name -eq "datadog-installer.exe" -and
        $_.CommandLine -match "postStartExperimentBackground"
    }
  register: remote_update_check

- name: Update remote update flag if installer is running
  ansible.builtin.set_fact:
    datadog_remote_update_in_progress: true
  when:
    - remote_update_check.stdout is defined
    - remote_update_check.stdout | trim | length > 0

But, it assumes that any output from the command is the installer exe running and skips later tasks.

If for instance you have a default profile script that includes any STDOUT text the Update remote update flag if installer is running task will be set to true even if the exe isn't running.

TASK [datadog.dd.agent : Check if remote update is in progress] ******************************************************************************************************************************************************
task path: /home/richard.dzien/.ansible/collections/ansible_collections/datadog/dd/roles/agent/tasks/windows_remote_update_check.yml:6
Using module file /usr/lib/python3.12/site-packages/ansible_collections/ansible/windows/plugins/modules/win_shell.ps1
Pipelining is enabled.
<server-01> ESTABLISH WINRM CONNECTION FOR USER: richard.dzien on PORT 5986 TO server-01
EXEC (via pipeline wrapper)
changed: [server-01] => {
    "changed": true,
    "cmd": "Get-CimInstance Win32_Process | Where-Object {\n    $_.Name -eq \"datadog-installer.exe\" -and\n    $_.CommandLine -match \"postStartExperimentBackground\"\n}",
    "delta": "0:00:04.157422",
    "end": "2026-02-18 14:15:49.011822",
    "rc": 0,
    "start": "2026-02-18 14:15:44.854400",
    "stderr": "",
    "stderr_lines": [],
    "stdout": "Setting up proxies, repositories and modules.\r\nShell proxy defaults are set.\r\n",
    "stdout_lines": [
        "Setting up proxies, repositories and modules.",
        "Shell proxy defaults are set."
    ]
}

TASK [datadog.dd.agent : Update remote update flag if installer is running] ******************************************************************************************************************************************
task path: /home/richard.dzien/.ansible/collections/ansible_collections/datadog/dd/roles/agent/tasks/windows_remote_update_check.yml:14
ok: [server-01] => {
    "ansible_facts": {
        "datadog_remote_update_in_progress": true
    },
    "changed": false
}

TASK [datadog.dd.agent : Inform about remote update in progress] *****************************************************************************************************************************************************
task path: /home/richard.dzien/.ansible/collections/ansible_collections/datadog/dd/roles/agent/tasks/windows_remote_update_check.yml:21
ok: [server-01] => {
    "msg": "Remote update is in progress. Skipping installation and restart of the Agent. Any changes to the configuration will only take effect at the next Agent restart, either manually or through a future role execution."
}

Fix is easy enough, the Update remote update flag if installer is running should also check for datadog-installer.exe in the output text.
I have tried this locally, and WFM.

- name: Update remote update flag if installer is running
  ansible.builtin.set_fact:
    datadog_remote_update_in_progress: true
  when:
    - remote_update_check.stdout is defined
    - remote_update_check.stdout | trim | length > 0
    - "'datadog-installer.exe' in remote_update_check.stdout"