Pull ansible-datadog (#155)

Co-authored-by: GitHub Actions Bot <>

Author: github-actions[bot]

roles/agent/handlers/main-win.yml

@@ -8,4 +8,4 @@
     name: datadogagent
     state: restarted
     force_dependent_services: true
-  when: datadog_enabled and not ansible_check_mode and ansible_facts.os_family == "Windows"
+  when: datadog_enabled and not ansible_check_mode and ansible_facts.os_family == "Windows" and not datadog_remote_update_in_progress

roles/agent/tasks/agent-win.yml

@@ -89,7 +89,7 @@
   ansible.windows.win_service:
     name: "{{ item }}"
     start_mode: manual
-  when: not datadog_skip_running_check and datadog_enabled and not ansible_check_mode
+  when: not datadog_skip_running_check and datadog_enabled and not ansible_check_mode and not datadog_remote_update_in_progress
   with_list:
     - datadog-trace-agent
     - datadog-process-agent
@@ -106,22 +106,33 @@
   ansible.windows.win_service:
     name: datadogagent
   register: datadog_service_info
-  when: not datadog_skip_running_check and datadog_enabled and not ansible_check_mode
+  when: not datadog_skip_running_check and datadog_enabled and not ansible_check_mode and not datadog_remote_update_in_progress
 
 - name: Ensure datadog-agent is running
   ansible.windows.win_service:
     name: datadogagent
     state: started
     start_mode: delayed
-  when: not datadog_skip_running_check and datadog_enabled and not ansible_check_mode and datadog_service_info.exists
+  when:
+    - not datadog_skip_running_check
+    - datadog_enabled
+    - not ansible_check_mode
+    - (datadog_service_info.exists | default(false))
+    - not datadog_remote_update_in_progress
   failed_when: false
   register: datadog_start_result
 
 - name: Wait and retry if service failed to start
   ansible.windows.win_service:
     name: datadogagent
     state: started
-  when: not datadog_skip_running_check and datadog_enabled and not ansible_check_mode and datadog_service_info.exists and datadog_start_result.failed
+  when:
+    - not datadog_skip_running_check
+    - datadog_enabled
+    - not ansible_check_mode
+    - (datadog_service_info.exists | default(false))
+    - (datadog_start_result.failed | default(false))
+    - not datadog_remote_update_in_progress
   delay: 10
   retries: 3
 
@@ -130,7 +141,7 @@
     name: "{{ item }}"
     state: stopped
     start_mode: disabled
-  when: not datadog_skip_running_check and not datadog_enabled
+  when: not datadog_skip_running_check and not datadog_enabled and not datadog_remote_update_in_progress
   with_list:
     - datadog-trace-agent
     - datadog-process-agent

roles/agent/tasks/main.yml

@@ -14,6 +14,11 @@
 - name: Check if OS is supported
   ansible.builtin.include_tasks: os-check.yml
 
+# Check for Windows remote updates before proceeding with installation
+- name: Windows remote update check
+  ansible.builtin.include_tasks: windows_remote_update_check.yml
+  when: ansible_facts.os_family == "Windows"
+
 - name: Fail if API key is missing
   ansible.builtin.fail:
     msg: "datadog_api_key is mandatory when using managed config"
@@ -64,11 +69,21 @@
   ansible.builtin.include_tasks: pkg-suse.yml
   when: ansible_facts.os_family == "Suse"
 
+# Windows variable initialization - always needed for configuration
+- name: Set windows NPM installed
+  ansible.builtin.set_fact:
+    agent_datadog_sysprobe_enabled: "{{ network_config is defined and 'enabled' in (network_config | default({}, true)) and network_config['enabled'] }}"
+  when: ansible_facts.os_family == "Windows"
+
+- name: Include Windows opts tasks
+  ansible.builtin.include_tasks: pkg-windows-opts.yml
+  when: ansible_facts.os_family == "Windows"
+
 # Note we don't check agent_datadog_skip_install variable value for windows here,
 # because some tasks in pkg-windows.yml are carried out regardless of its value.
 - name: Windows Install Tasks
   ansible.builtin.include_tasks: pkg-windows.yml
-  when: ansible_facts.os_family == "Windows"
+  when: ansible_facts.os_family == "Windows" and not datadog_remote_update_in_progress
 
 - name: MacOS Install Tasks
   ansible.builtin.include_tasks: pkg-macos.yml

roles/agent/tasks/parse-version-windows.yml

@@ -19,3 +19,20 @@
   failed_when: false
   check_mode: false
   when: ansible_facts.os_family == "Windows"
+
+- name: Parse installed Windows Agent version into components
+  ansible.builtin.set_fact:
+    agent_datadog_installed_version: "{{ agent_datadog_version_check_win.stdout | trim |
+      regex_search(installed_agent_regexp, '\\g<major>', '\\g<minor>', '\\g<bugfix>') }}"
+  vars:
+    installed_agent_regexp: (?P<major>[0-9]+)\.(?P<minor>[0-9]+)\.(?P<bugfix>[0-9]+)
+  when: >-
+    ansible_facts.os_family == "Windows" and
+    agent_datadog_version_check_win.stdout | trim | length > 0
+
+- name: Set installed version component vars
+  ansible.builtin.set_fact:
+    agent_datadog_installed_major: "{{ agent_datadog_installed_version.0 | default('', true) | string }}"
+    agent_datadog_installed_minor: "{{ agent_datadog_installed_version.1 | default('', true) | string }}"
+    agent_datadog_installed_bugfix: "{{ agent_datadog_installed_version.2 | default('', true) | string }}"
+  when: ansible_facts.os_family == "Windows" and agent_datadog_version_check_win.stdout | trim | length > 0

roles/agent/tasks/pkg-windows-opts.yml

@@ -125,3 +125,41 @@
   when: >-
     (agent_datadog_skip_install and (agent_datadog_major | int <= 7) and (agent_datadog_minor | int < 45)) and
     (("NPM" in agent_windows_active_features.stdout_lines) != agent_datadog_sysprobe_enabled)
+
+# Check if downgrade is requested (installed version is higher than requested version)
+- name: Initialize downgrade detection flag
+  ansible.builtin.set_fact:
+    agent_datadog_downgrade_detected: false
+
+- name: Detect if downgrade is requested
+  ansible.builtin.set_fact:
+    agent_datadog_downgrade_detected: true
+  when: >-
+    agent_datadog_installed_major is defined and
+    agent_datadog_installed_minor is defined and
+    agent_datadog_installed_bugfix is defined and
+    (
+      (agent_datadog_installed_major | int > agent_datadog_major | int) or
+      (agent_datadog_installed_major | int == agent_datadog_major | int and
+       agent_datadog_installed_minor | int > agent_datadog_minor | int) or
+      (agent_datadog_installed_major | int == agent_datadog_major | int and
+       agent_datadog_installed_minor | int == agent_datadog_minor | int and
+       agent_datadog_installed_bugfix | int > agent_datadog_bugfix | int)
+    )
+
+# Skip downgrade warning if remote update is in progress
+- name: Warn about downgrade
+  ansible.builtin.debug:
+    msg: >-
+      datadog_agent_version {{ agent_datadog_major }}.{{ agent_datadog_minor }}.{{ agent_datadog_bugfix }}
+      is lower than installed version
+      {{ agent_datadog_installed_major }}.{{ agent_datadog_installed_minor }}.{{ agent_datadog_installed_bugfix }},
+      proceeding to downgrade by uninstalling current version first
+  when: agent_datadog_downgrade_detected and not datadog_remote_update_in_progress
+
+# We do not need to check for remote update in progress here because installation is skipped if remote update is in progress anyway
+- name: Force reinstall for downgrade
+  ansible.builtin.set_fact:
+    agent_datadog_skip_install: false
+    agent_datadog_force_reinstall: true
+  when: agent_datadog_downgrade_detected

roles/agent/tasks/pkg-windows.yml

@@ -1,12 +1,5 @@
 ---
-## must be prior to `pkg-windows-opts.yml`, because the variable is used inside
-- name: Set windows NPM installed
-  ansible.builtin.set_fact:
-    agent_datadog_sysprobe_enabled: "{{ network_config is defined and 'enabled' in (network_config | default({}, true)) and network_config['enabled'] }}"
-
-## Might override agent_datadog_skip_install
-- name: Include Windows opts tasks
-  ansible.builtin.include_tasks: pkg-windows-opts.yml
+# Note: Windows opts tasks and NPM setup are now included in main.yml to ensure variables are set even during remote updates
 
 - name: Force skip install when requested
   ansible.builtin.set_fact:

roles/agent/tasks/windows_remote_update_check.yml

@@ -0,0 +1,27 @@
+---
+- name: Initialize remote update flag
+  ansible.builtin.set_fact:
+    datadog_remote_update_in_progress: false
+
+- 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
+
+- name: Inform about remote update in progress
+  ansible.builtin.debug:
+    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.
+  when: datadog_remote_update_in_progress