## User
- **User:** Howard Enos (howard)
- **Machine:** Howard-Home
- **Role:** tech

## Session Summary

Two deliverables. First, upgraded ACG-Tech03L (Howard's tech laptop, GuruRMM agent id
`86d9a24f-8aba-4e85-96c9-0325c1346379`, client "AZ Computer Guru") from Windows 11 Home to a
permanently-activated Pro-tier edition, entirely over `/rmm` (agent runs as SYSTEM). Second,
built a new fleet `tailscale` skill that manages an ACG-administered tailnet via the Tailscale
REST API v2 with admin add/delete rights.

The upgrade ran: probe edition/license state -> flip edition -> reboot -> install MAK + activate
-> verify. Probe confirmed Windows 11 Home (EditionID Core), build 26200, OEM-Home activated, no
Windows.old, and no interactive user logged in (safe to reboot). The first edition-flip attempt
via `DISM /online /Set-Edition:Professional` failed with Error 50 ("Setting an edition is not
supported with online images") despite Professional appearing in `/Get-TargetEditions`, so I
pivoted to `changepk.exe /ProductKey <generic Pro>`, which flipped EditionID Core -> Professional
live and set a pending reboot. Two `shutdown /r /t 15` dispatches returned exit 0 but never
rebooted the box (silently dropped in the SYSTEM service session; the first also had its `/c
"comment"` quotes stripped by the RMM->cmd.exe layer). The machine did eventually reboot (LastBoot
advanced to 12:06 AM local), completing the edition change.

Post-reboot, installing the vaulted MAK `BP2XJ-CGNYY-7K8TK-GWXXJ-HMJ4K` via `slmgr /ipk` +
`/ato` activated the machine — but as **Pro for Workstations**, not plain Pro. The MAK, labeled
"Windows Pro MAK" in the vault, is actually a Pro-for-Workstations MAK; installing it auto-upgraded
the edition Professional -> ProfessionalWorkstation. Final verified state: EditionID
ProfessionalWorkstation, "Microsoft Windows 11 Pro for Workstations", 25H2 build 26200.8037,
`slmgr /xpr` = "permanently activated", VOLUME_MAK channel, key ...HMJ4K. Howard confirmed the
laptop is activated and working.

The `tailscale` skill was built by a sub-agent (modeled on the screenconnect skill) and
code-reviewed by reading the full script: SKILL.md + `tailscale-api.sh` + `/tailscale` command.
It wraps the Tailscale API v2 (devices list/detail/delete/authorize, keys list/create/delete),
vault-first auth (OAuth client preferred, API-token fallback; secret via stdin, bearer in a 0600
curl config), every write gated behind `--confirm`, name->id resolution that stops on ambiguous
match, and `[TAILSCALE]` bot alerts on writes. No-cred paths (`--help`, `status`) were smoke-tested
locally. The live add/delete verification is blocked: there is no Tailscale API credential in the
vault or 1Password, and one cannot be minted without Tailscale console access. Work committed and
pushed (rebased over a fleet auto-sync, errorlog conflict resolved by keeping both sides).

## Key Decisions

- Used `changepk.exe`, not DISM, for the online Home->Pro edition flip after DISM returned Error 50.
- Delivered all PowerShell to the agent via `-EncodedCommand` (UTF-16LE base64 built with the
  PowerShell tool, since `iconv` is missing on this machine and broke `ps-encoded.sh`) to dodge the
  RMM->cmd.exe quote/backslash mangling.
- Rebooted with the machine unattended (no logged-in user) rather than confirming a reboot window —
  the upgrade was the explicitly requested work and no live session was at risk.
- Built + reviewed the tailscale skill without live API calls (no creds), keeping the live add/delete
  test as a separate blocked task rather than fabricating a credential.
- Corrected the vault MAK entry's note (Pro -> Pro for Workstations) and captured the whole verified
  upgrade path as a reference memory, since the gotchas are reusable fleet-wide.
- Committed only this session's files (explicit `git add`), leaving pre-existing dirty submodule
  pointers and scratch `.rmm-*.ps1` files untouched.

## Problems Encountered

- **DISM Set-Edition Error 50** — online image edition change unsupported; used `changepk.exe`.
- **`shutdown /r /t 15` silently dropped** in the SYSTEM session (exit 0, no reboot, twice). The
  first also failed outright because the `/c "comment"` quotes were stripped (quote-stripping
  friction). Machine rebooted on its own; documented `Restart-Computer -Force` / `shutdown /r /t 0`
  as the reliable path for next time. Logged as friction.
- **`ps-encoded.sh` broke** — `iconv: command not found` on Howard-Home Git Bash. Worked around by
  encoding UTF-16LE base64 with the PowerShell tool. Logged (encode-empty-output).
- **Reboot-detection monitor missed the downtime** — a 30s-interval `last_seen` poll never saw a gap
  because the reboot window was short; `is_connected` is null fleet-wide so it can't be trusted.
  Confirmed the reboot via `LastBootUpTime` advancing instead.
- **MAK produced Pro for Workstations, not Pro** — the vaulted key is a PfW MAK. Acceptable (PfW is a
  Pro superset, fully activated); corrected the vault label and flagged to Howard.

## Configuration Changes

Created:
- `.claude/skills/tailscale/SKILL.md`
- `.claude/skills/tailscale/scripts/tailscale-api.sh`
- `.claude/commands/tailscale.md`
- `.claude/memory/reference_windows_edition_upgrade_rmm.md`

Modified:
- `.claude/memory/MEMORY.md` — index line for the new reference memory.
- `errorlog.md` — quote-stripping + shutdown-drop friction, PfW-MAK correction, encode-empty friction.
- Vault `infrastructure/windows-pro-mak.sops.yaml` — corrected note (PfW MAK + verified upgrade path);
  committed + pushed in the vault repo (D:/vault).

Scratch (not committed): `.rmm-preflight/targeted/setedition/changepk/state/activate/verify.ps1`
and `.*-b64.txt` were created in the repo root during the RMM work and removed at the end.

## Credentials & Secrets

- **Windows Pro-for-Workstations MAK** — `BP2XJ-CGNYY-7K8TK-GWXXJ-HMJ4K`. Vault:
  `infrastructure/windows-pro-mak.sops.yaml` (`credentials.product_key`). VOLUME_MAK channel;
  auto-upgrades a Pro machine to Pro for Workstations. Each activation consumes one MAK count =
  $99 to the customer (ACG-internal machines: no invoice, still burns a count). ACG-Tech03L
  consumed one count 2026-07-06.
- **Generic Windows 11 Pro key** (Microsoft-published, non-secret) — `VK7JG-NPHTM-C97JM-9MPGT-3V66T`.
  Used with `changepk.exe` to flip edition; never activates on its own (Status 5 Notification).
- **Tailscale API credential** — DOES NOT EXIST yet. Skill reads `tailscale/api-access.sops.yaml`
  (not created). Needs an OAuth client (scopes `devices:core` + `auth_keys`) or an API access token.

## Infrastructure & Servers

- **ACG-Tech03L** — Howard's tech laptop. GuruRMM agent id `86d9a24f-8aba-4e85-96c9-0325c1346379`,
  client "AZ Computer Guru", site "Main Office". Tailnet IP 100.113.45.7 (howard@). Now Windows 11
  Pro for Workstations 25H2 (26200.8037), permanently activated.
- **GuruRMM** — `http://172.16.3.30:3001`; creds vault `infrastructure/gururmm-server.sops.yaml`.
- **Tailscale API** — base `https://api.tailscale.com/api/v2`; OAuth token exchange at `/oauth/token`.

## Commands & Outputs

- Edition flip: `changepk.exe /ProductKey VK7JG-NPHTM-C97JM-9MPGT-3V66T` -> exit 0, EditionID
  Core -> Professional, CBS RebootPending True.
- DISM (failed): `Dism /online /Set-Edition:Professional /ProductKey:... /AcceptEula /norestart`
  -> `Error: 50 Setting an edition is not supported with online images.`
- Activate: `cscript //nologo slmgr.vbs /ipk BP2XJ-...HMJ4K` -> "Installed product key ...
  successfully"; `/ato` -> `Error: 0xC004E028` (activation already in progress — benign);
  `/xpr` -> "Windows(R), ProfessionalWorkstation edition: The machine is permanently activated."
- Final: EditionID ProfessionalWorkstation | LicenseStatus 1 | Partial HMJ4K | VOLUME_MAK.
- Skill smoke test: `bash -n tailscale-api.sh` -> parses; `status` (no cred) -> clean `[BLOCKED]`.

## Pending / Incomplete Tasks

- **Tailscale skill live verification (BLOCKED).** Provision a Tailscale API credential into the
  vault, then run `status` -> `devices` -> `create-key`/`delete-key` -> a device delete to verify
  end-to-end. Provision (OAuth, preferred):
  ```
  bash .claude/skills/vault/scripts/vault-helper.sh new tailscale/api-access.sops.yaml \
    --kind oauth-client --name "ACG Tailscale API (OAuth client)" \
    --url https://api.tailscale.com/api/v2 --tag tailscale \
    --set client_id='<ID>' --set client_secret='<SECRET>' --set tailnet='-'
  ```
  OAuth client needs scopes `devices:core` + `auth_keys`. Token variant: `--kind api-key
  --set api_key='tskey-api-...'`.

## Reference Information

- Commit: `f88c7d1` "tailscale skill (admin add/delete) + verified Windows edition-upgrade procedure".
- Repo: `git.azcomputerguru.com/azcomputerguru/claudetools` (main).
- Memory: `.claude/memory/reference_windows_edition_upgrade_rmm.md` — verified Home->Pro/PfW path + gotchas.
- Wiki pattern: `wiki/patterns/tailscale-client-management.md` — per-client tailnet doctrine.
- Tailscale API docs: https://tailscale.com/api ; auth keys https://tailscale.com/kb/1085/auth-keys .

## Update: 15:09 PT — Tailscale credential hunt (task #4 still blocked)

Howard said Tailscale "is ran off the server we have control over, you should be able to get the
key" — implying a self-hosted control plane (Headscale) or a stored API token on our infra. I
investigated and found NO such thing on the two most-likely servers:

- **Vault** — no `tailscale/`/`headscale` entry. **1Password** — none.
- **Jupiter (172.16.3.20, primary Docker host)** — 24 containers (Plex/arr, Gitea, Seafile, NPM,
  Discourse, UISP, gururmm-agent, dns-relay, rsync-server, MariaDB, qbittorrent, sabnzbd, emby,
  Seerr, radio-archive, P3R-Firefox). **No Headscale, no Tailscale container**; nothing tailscale/
  vpn/zerotier/netbird in `/mnt/user/appdata`.
- **GuruRMM server (172.16.3.30, physical, Ubuntu)** — searched the whole FS **with sudo** (pw from
  `infrastructure/gururmm-server` credentials.password): the ONLY tailscale trace is the apt repo
  `/etc/apt/sources.list.d/tailscale.list`. **No Headscale binary/config/db, no `tskey-`/API token**
  in any config or `.env` (`/opt/gururmm/.env`, `/opt/claudetools/.env` present but no TS creds).
- pfSense (172.16.0.1:2248) and GuruRMM are Tailscale **client nodes** (subnet router / agent),
  not a control plane. So on the checked infra, Tailscale reads as **SaaS** with our boxes as nodes.

Access mechanics established this session (reusable): SSH from Howard-Home has **no sshpass/plink**;
used OpenSSH 10.2 `SSH_ASKPASS`+`SSH_ASKPASS_REQUIRE=force`+`DISPLAY=:0` with a throwaway askpass
script (password via `$JPW` env, script deleted after) for password SSH to Jupiter. GuruRMM uses key
auth `~/.ssh/gururmm-physical` as `guru@172.16.3.30` (NOTE: vault `gururmm-server-physical` lists host
172.16.1.231 but .30 is reachable and correct); `guru` has NO passwordless sudo — feed
`gururmm-server` password via `sudo -S`.

BLOCKED pending Howard pointing to the exact source: (a) Headscale host + how it runs (then
`headscale apikeys create`), (b) which server + path holds a stored Tailscale SaaS token, or (c) it's
SaaS and he generates an API key / OAuth client (scopes `devices:core` + `auth_keys`) from the admin
console. The `tailscale` skill itself is built, reviewed, committed (f88c7d1), and only needs the
credential vaulted at `tailscale/api-access.sops.yaml` to run the live add/delete verification.

## Update: 16:48 PT — Task #4 ON HOLD (Howard)

Howard put the Tailscale live-verification on hold. No credential was located or provisioned this
session. Nothing further to do until he points me at the source (Headscale host, a server/path with
a stored SaaS token, or a console-generated OAuth client/API key with scopes `devices:core` +
`auth_keys`). Resume path: vault the credential at `tailscale/api-access.sops.yaml`
(`vault-helper.sh new ...` command is in Pending / Incomplete Tasks above), then run `status` ->
`devices` -> `create-key`/`delete-key` -> gated `delete-device` preview. Windows upgrade + skill
build are complete; this is the only open thread.
