maintenance-scripts/playbooks/check_updates.yml

---
- name: Check Package Updates with Risk Assessment
  hosts: all
  gather_facts: true
  vars:
    openai_api_key: "{{ lookup('env', 'OPENAI_API_KEY') }}"
    openai_api_url: "https://api.openai.com/v1/chat/completions"
    openai_model: "gpt-4o"
    output_file: "/tmp/update_report_{{ ansible_date_time.iso8601_basic_short }}.json"
    temp_update_file: "/tmp/available_updates.json"

  tasks:
    - name: Validate OpenAI API key is present
      fail:
        msg: "OPENAI_API_KEY environment variable is required"
      when: openai_api_key | length == 0

    - name: Detect OS family and set package manager
      set_fact:
        pkg_mgr: "{{ 'apt' if ansible_os_family == 'Debian' else 'apk' if ansible_os_family == 'Alpine' else 'unknown' }}"

    - name: Update package cache (Debian/Ubuntu)
      apt:
        update_cache: true
        cache_valid_time: 3600
      when: ansible_os_family == 'Debian'

    - name: Update package cache (Alpine)
      apk:
        update_cache: true
      when: ansible_os_family == 'Alpine'

    - name: List upgradable packages (Debian/Ubuntu)
      shell: apt list --upgradable 2>/dev/null | tail -n +2 | awk -F'/' '{print $1 "\t" $2}'
      register: upgradable_debian
      changed_when: false
      when: ansible_os_family == 'Debian'

    - name: List upgradable packages (Alpine)
      shell: apk version -l '<'
      register: upgradable_alpine
      changed_when: false
      when: ansible_os_family == 'Alpine'

    - name: Parse upgradable packages (Debian/Ubuntu)
      set_fact:
        upgradable_packages: >-
          {{ upgradable_debian.stdout.split('\n') | select('match', '^.+\t.+$') |
             map('regex_replace', '^(.+?)\\t(.+)$', '{\"name\": \"\\1\", \"new_version\": \"\\2\"}') |
             map('from_json') | list }}
      when: ansible_os_family == 'Debian'

    - name: Parse upgradable packages (Alpine)
      set_fact:
        upgradable_packages: >-
          {{ upgradable_alpine.stdout.split('\n') | select('match', '^.+\s+<\s+.+$') |
             map('regex_replace', '^(.+?)\\s+<\\s+(.+)$', '{\"name\": \"\\1\", \"new_version\": \"\\2\"}') |
             map('from_json') | list }}
      when: ansible_os_family == 'Alpine'

    - name: Get current versions of upgradable packages (Debian/Ubuntu)
      shell: dpkg-query -W -f='${Package}\t${Version}\n' {{ item.name }}
      register: current_versions_debian
      changed_when: false
      loop: "{{ upgradable_packages }}"
      loop_control:
        loop_var: item
      when: ansible_os_family == 'Debian'

    - name: Get current versions of upgradable packages (Alpine)
      shell: apk info -vv | grep "{{ item.name }}-" | awk '{print $1}'
      register: current_versions_alpine
      changed_when: false
      loop: "{{ upgradable_packages }}"
      loop_control:
        loop_var: item
      when: ansible_os_family == 'Alpine'

    - name: Build complete package update list (Debian/Ubuntu)
      set_fact:
        package_update_list: >-
          {{ current_versions_debian.results |
             map(attribute='stdout') |
             zip(upgradable_packages) |
             map('regex_replace', '^(.+?)\\t(.+)$', '{\"name\": \"\\1\", \"current_version\": \"\\2\"}') |
             map('from_json') |
             product(upgradable_packages) |
             map('combine') |
             list }}
      when: ansible_os_family == 'Debian'

    - name: Build complete package update list (Alpine)
      set_fact:
        package_update_list: >-
          {{ current_versions_alpine.results |
             map(attribute='stdout') |
             zip(upgradable_packages) |
             map('regex_replace', '^(.+?)-([0-9].+)$', '{\"name\": \"\\1\", \"current_version\": \"\\2\"}') |
             map('from_json') |
             product(upgradable_packages) |
             map('combine') |
             list }}
      when: ansible_os_family == 'Alpine'

    - name: Prepare package list for OpenAI analysis
      set_fact:
        packages_for_analysis: >-
          {{ package_update_list | map('to_json') | join('\n') }}

    - name: Create OpenAI prompt for risk assessment
      set_fact:
        openai_prompt: >-
          Analyze the following package updates for potential breaking changes or disruptions.
          Identify which packages might cause issues based on version changes.
          Return a JSON array with package names and a boolean "risk" field (true if risky, false if safe).
          Packages:
          {{ packages_for_analysis }}

    - name: Send request to OpenAI for risk assessment
      uri:
        url: "{{ openai_api_url }}"
        method: POST
        headers:
          Authorization: "Bearer {{ openai_api_key }}"
          Content-Type: "application/json"
        body_format: json
        body:
          model: "{{ openai_model }}"
          messages:
            - role: system
              content: "You are a package update risk assessment assistant. Analyze package updates and identify potential breaking changes or disruptions. Return only valid JSON."
            - role: user
              content: "{{ openai_prompt }}"
          temperature: 0.3
          response_format: { "type": "json_object" }
      register: openai_response
      until: openai_response.status == 200
      retries: 3
      delay: 5
      failed_when: openai_response.status != 200

    - name: Parse OpenAI risk assessment
      set_fact:
        risk_assessment: "{{ openai_response.json.choices[0].message.content | from_json }}"

    - name: Merge risk assessment with package list
      set_fact:
        packages_with_risk: >-
          {{ package_update_list |
             map('combine', {'risk': risk_assessment | selectattr('name', 'equalto', item.name) | map(attribute='risk') | first | default(false)}) |
             list }}
      loop: "{{ package_update_list }}"
      loop_control:
        loop_var: item

    - name: Separate safe and risky packages
      set_fact:
        safe_updates: "{{ packages_with_risk | selectattr('risk', 'equalto', false) | list }}"
        risky_updates: "{{ packages_with_risk | selectattr('risk', 'equalto', true) | list }}"

    - name: Generate update report
      copy:
        dest: "{{ output_file }}"
        content: >-
          {
            "hostname": "{{ ansible_hostname }}",
            "ip_address": "{{ ansible_default_ipv4.address }}",
            "os": "{{ ansible_distribution }} {{ ansible_distribution_version }}",
            "scan_date": "{{ ansible_date_time.iso8601 }}",
            "total_updatable_packages": {{ packages_with_risk | length }},
            "safe_updates_count": {{ safe_updates | length }},
            "risky_updates_count": {{ risky_updates | length }},
            "safe_updates": {{ safe_updates | to_json }},
            "risky_updates": {{ risky_updates | to_json }},
            "can_proceed_with_update": {{ risky_updates | length == 0 }}
          }
        mode: '0600'

    - name: Display update summary
      debug:
        msg:
          - "Total upgradable packages: {{ packages_with_risk | length }}"
          - "Safe updates: {{ safe_updates | length }}"
          - "Risky updates: {{ risky_updates | length }}"
          - "Can proceed with automatic update: {{ risky_updates | length == 0 }}"
          - "Report saved to: {{ output_file }}"

    - name: Return update findings
      set_fact:
        update_report:
          hostname: ansible_hostname
          ip_address: ansible_default_ipv4.address
          os: ansible_distribution + ' ' + ansible_distribution_version
          total_updatable_packages: packages_with_risk | length
          safe_updates: safe_updates
          risky_updates: risky_updates
          can_proceed_with_update: risky_updates | length == 0
          scan_date: ansible_date_time.iso8601
          report_file: output_file