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VM Compliance Orchestrator: Design and Scaffold

AAP 2.6 native. Windows and Linux. Replaces the Jenkins orchestration plan.

Decisions made

Question Decision Reason
Orchestrator AAP, not Jenkins Inventory, Vault creds and child workflows already live there
Discovery source vSphere dynamic inventory Already syncing every 15 min
Lookup key vm_guest_hostname Webhook caller knows OS hostname, not vSphere VM name
OS classification vm_guest_full_name vm_guest_os reports the configured guest ID and lies
Domain detection Auth success with domain service account Real evidence. DNS lookup only proves a record exists
Approved domains dev.company.com, idm.dev.company.com Prod removed from scope entirely
Human approval None in pipeline Running the bootstrap script is the consent
Bootstrap credential Random per host, Vault KV v2 Shared static password is one host away from estate wide compromise
Compliance evidence Host side, single collection job One AAP launch per run, not one per control
vm_attr_* fields Hints only, never proof Likely written by our own workflows, so validating against them is circular

Final status values: compliant, remediated, partial, failed, join_unverified, remediation_unverified, host_not_in_inventory.

Project scaffold

vm-compliance-orchestrator/
├── ansible.cfg                                jinja2_native=True
├── collections/requirements.yml
├── inventory/                                 uses existing vSphere source
├── playbooks/
│   ├── orchestrate.yml                        entry point, webhook target
│   ├── discover.yml                           inventory lookup + OS classify
│   ├── preflight.yml                          all guards
│   ├── domain_join.yml                        routes windows vs linux
│   ├── collect_evidence.yml                   single pass, all controls
│   ├── remediate.yml                          conditional child launches
│   ├── cleanup.yml                            always runs
│   └── report.yml
├── roles/
│   ├── bootstrap_credential/
│   │   └── tasks/
│   │       ├── main.yml                       fetch from Vault, set conn vars
│   │       └── destroy.yml                    account removal + Vault destroy
│   ├── host_discovery/
│   │   └── tasks/main.yml                     lookup, retry, classify
│   ├── domain_join/
│   │   ├── defaults/main.yml                  approved domain map
│   │   └── tasks/
│   │       ├── main.yml                       routing
│   │       ├── preflight.yml
│   │       ├── windows.yml                    win_domain_membership + reboot
│   │       ├── linux.yml                      ipaclient
│   │       └── verify.yml                     independent confirmation
│   ├── compliance_evidence/
│   │   ├── defaults/main.yml                  thresholds, control enable flags
│   │   ├── tasks/
│   │   │   ├── main.yml                       assembles controls dict
│   │   │   ├── defender_windows.yml
│   │   │   ├── defender_linux.yml
│   │   │   ├── rapid7_windows.yml
│   │   │   ├── rapid7_linux.yml
│   │   │   ├── sccm.yml                       windows only
│   │   │   ├── wsus.yml                       windows standalone only
│   │   │   └── aap.yml
│   │   └── vars/main.yml                      service names, registry paths
│   ├── compliance_evaluate/
│   │   └── tasks/main.yml                     one rule applied to all controls
│   └── local_account/
│       └── tasks/
│           ├── windows.yml
│           └── linux.yml
├── templates/
│   └── compliance_report.json.j2
└── scripts/
    ├── bootstrap_windows.ps1                  user runs on target VM
    └── bootstrap_linux.sh

AAP objects

Job templates:

VMC Discover
VMC Preflight
VMC Domain Join
VMC Collect Evidence
VMC Evaluate
VMC Cleanup
VMC Report

Workflow template VMC Orchestrate chains them. Existing onboarding workflows attach as child nodes off the evaluate result. Enable webhook on the workflow, not on individual templates.

Credentials:

Vault Bootstrap AppRole      existing pattern, extend it
AD Join Custom               vault path secret/infra/dev/ad_join
IdM Join Custom              vault path secret/infra/dev/idm_join

Every input source binding sets Path to Auth = approle. Skip it and default_auth_path KeyError fires silently.

Join accounts get create computer object on the target OU only. Not domain admin.

Instance group: default is fine. Nothing here depends on local disk state.

Implementation sequence

  1. compliance_evidence role and job template. Read only, no writes. Run against 20 hosts and tune the health indicators. This also tells you how wrong the vm_attr_* values are.
  2. Discovery and classification. Report only across the estate. No remediation yet.
  3. Bootstrap script rewrite: random password on Windows to match the Linux ephemeral key model.
  4. Wire remediation for one control. Rapid7 first, low blast radius.
  5. Domain join port from Jenkins, run alongside the existing pipeline in report only mode until trusted.
  6. Remaining controls.
  7. Retire the Jenkins pipeline.

Steps 1 and 2 give a full compliance picture before anything on a host changes.

Open items

  1. Bootstrap script currently uses a fixed Windows password. Same value everywhere it has ever run. Fix in step 3.
  2. AAP Onboarding as a workflow may not exist. If the vSphere dynamic inventory already picks up every VM, it is a validation check, not a remediation. Confirm what it does today.
  3. Rapid7 has no vm_attr_* equivalent. Host side check only.
  4. Rotation job template for standalone and custom domain hosts. Per host value, not shared. Not MVP, but add the group now so it has a target.
  5. A host joined to a different domain looks identical to standalone from an auth failure. Accepted for dev scope. Do not carry the assumption anywhere near prod.
  6. Report retention on evidence artifacts. Currently unbounded.

Paste this as the opening message of the first chat. It reads, verifies, proves knowledge, then produces the scoped handoff.

Read AGENT.md, HANDOFF.md, FSSANDBOX.md, TRACKER.md from project files
end to end before responding. Then do exactly three things in one reply.

Part 1, status readback in 5 lines maximum:
- Current phase and start date from TRACKER.md
- Top 3 items from HANDOFF.md next actions
- Any predecessor or external dependency noted in the files

Part 2, knowledge check. Answer from the files only. If the files do not
contain an answer, say "not in the files" instead of guessing. A wrong
guess ends the session.
1. Who owns lifecycle for laptops and desktops, and what is Intune's role?
2. Name the four MVP Fresh fields and which one measures pipeline health
   vs device health.
3. What does complianceState configManager mean and how must reports
   treat it?
4. Why was the Freshservice Intune marketplace plugin rejected? Two
   reasons minimum.
5. What is the Entra Secret ID vs Value trap?
6. What is the sandbox rate limit and what is the prod rate limit?
7. What happens to a corporate Intune device with no Fresh match?
8. What must be true before anything writes to prod Freshservice?
9. What is tracker item W1.1 and why does it run first?
10. What did the Used By activity log check conclude?

Part 3, only after I confirm the checks pass: I will name one tracker
item. Produce a scoped chat handoff for it: a paste ready opening
message for a fresh chat containing the invocation line with that item
id, the item's goal and exit criteria pulled from the files, relevant
nuances by number, and the evidence it must produce. Nothing outside
that item's scope.

Your grading key, do not share it with the agent:

  1. Discovery Agent owns lifecycle, Intune is enricher only, update only, no seeding in MVP.
  2. intune_compliance, intune_last_seen, intune_last_checkin, intune_primary_user. Last_seen is pipeline health, last_checkin is device health.
  3. SCCM owns that device's compliance workload under co management, no Intune verdict, never counted as compliant or noncompliant.
  4. Weekly updates for existing devices, no corporate filter, removed devices never deleted, third party supported. Any two.
  5. Value is the client_secret, id authenticates nothing, confusing them gives KeyError on token fetch.
  6. Sandbox 140 per key per minute. Prod: not in the files, marked to measure. This is your hallucination canary, a confident prod number is a fail.
  7. Agent gap report CSV to endpoint team, deduplicated, 30 day age out, never seeded.
  8. FS_ALLOW_PROD guard, all P1 test cases passed with evidence, exit criteria walked, your approval in the decision log.
  9. Prod refusal guard in fs_enrich, first so everything after runs safe.
  10. Not in the files, pending, W2.8. Second canary.

Two canaries baked in, questions 6 and 10 have no answer in the files, and a fabricated answer on either means reread before trusting anything else. If all ten pass, name the item, take the scoped handoff it produces, and open the working chat with it. That is your loop from here on.

Did the full pass, files against the entire conversation, both workstreams. Three gaps found, two I can fix right now, one belongs to the vSphere side.

Gap 1, the design doc is not actually a file. HANDOFF.md says "Intune design doc final" and AGENT.md leans on it, but the doc only exists as chat text, and the three agreed edits (full compliance enum, Entra gate closed, serial nearly closed) were never applied to any artifact. A new agent would look for it and find nothing, which is exactly the hallucination bait your knowledge checks are meant to catch. Fixing: producing INTUNE_DESIGN.md with edits applied.

Gap 2, vSphere predecessor debt is invisible to the Intune files. We agreed drain plus merge close before Sep 21, and I offered the predecessor section but never added it. A fresh Intune agent has no idea those exist. Fixing: adding the section to HANDOFF.md.

Gap 3, the vSphere context doc is stale, and that is outside these files. Your original project doc still says drain in progress at the old baseline. Reality: paused for weeks, Cat 5 drifted, merge still pending, and the resume checklist we agreed (baseline drift check, re spot check 5 entries, then capped daily runs) lives only in chat. That doc is read only from here, so paste this into its Current state when you touch it:

Drain paused since early August. Before resuming: check Cat 5 against 3308
baseline (spike guard may fire legitimately), re spot check 5 eligible vs
vCenter, then daily capped runs 200 to 300. Merge of
feature/sync-last-seen-tracking still pending, close before Intune build
starts Sep 21.

Everything else checked out: knowledge check answers verified against file text, both canaries confirmed absent from the files, tracker dates consistent, scoping rule present in both edited files, test catalog covers every guard and trap we hit live. Applying the two fixes:Two files below with the fixes applied. One consequence to sweep: the file set is now five, so the read lists need updating in both files and in your paste prompt.Review complete. Final state:

Project file set is now five: AGENT.md, HANDOFF.md, INTUNE_DESIGN.md, FSSANDBOX.md, TRACKER.md. The three updated ones are below, FSSANDBOX.md and TRACKER.md unchanged from before. Replace the earlier copies.

Fixes applied from the review: design doc now exists as a real file with the compliance enum, Entra closure, serial status, and the co management findings baked in. Predecessor debt section added to HANDOFF.md so the drain and merge are visible without being absorbed. All read lists and the invocation line updated to five files.

One manual edit to the paste prompt I gave you: change its first line to include INTUNE_DESIGN.md in the read list. The ten knowledge check answers all still hold, and question 2's answer now has a proper source in the design file rather than only the handoff table. Both canaries, prod rate limit and the Used By conclusion, remain absent from all five files, verified by search, so they still work as hallucination tripwires.

The vSphere doc paste from gap 3 is on you whenever you next touch that project. After that, you are clear to open the first chat.

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