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claudetools/session-logs/2026-04-21-session.md

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Session Log — 2026-04-21

User

  • User: Mike Swanson (mike)
  • Machine: DESKTOP-0O8A1RL
  • Role: admin

Session Summary

Continuation from previous conversation (context compacted). This session covered three areas:

  1. BirthBiologic vault save — fixed a broken vault stub and saved GuruRMM site credentials for the new BirthBiologic client
  2. MSI build fix — diagnosed and fixed "MSI build on Pluto failed" error caused by a missing WiX extension flag in install.rs
  3. DESIGN.md created — comprehensive per-component design guide for GuruRMM covering architectural decisions, rules, and constraints that were previously only in session logs and verbal decisions

Key Work

1. BirthBiologic Vault Entry — Fixed and Saved

Problem: A broken unencrypted stub existed at D:/vault/clients/birthbiologic/gururmm-site-main.sops.yaml. vault.sh add failed ("file already exists"), vault.sh create doesn't exist, and sops --encrypt failed with "no matching creation rules found" when the input file wasn't named .sops.yaml.

Root cause: The SOPS .sops.yaml creation rule uses path_regex: '.*\.sops\.yaml$' — it only matches files already named .sops.yaml. Attempting to encrypt a .plain.yaml file doesn't match the rule.

Fix:

  1. Deleted the broken stub
  2. Wrote plaintext to gururmm-site-main.plain.yaml
  3. Encrypted with explicit AGE key + --encrypted-regex flags: sops --encrypt --age age1qz7ct84m50u06h97artqddkj3c8se2yu4nxu59clq8rhj945jc0s5excpr --encrypted-regex '^(credentials|...)$' input.plain.yaml > output.sops.yaml
  4. Deleted plaintext
  5. Verified: vault.sh get-field clients/birthbiologic/gururmm-site-main.sops.yaml credentials.api_key returned correct value

BirthBiologic GuruRMM credentials (also in vault):

client_id: da526b38-e832-4159-ab13-a3d94e9897a2
site_id: 3b20ef97-c764-4ef8-9154-79c3d5b486f8
site_code: BRIGHT-PEAK-5980
api_key: grmm_1ZB1qV9Q61b9Noq8BIaZGwLNjZMfF49i
installer_url (landing): https://rmm.azcomputerguru.com/install/BRIGHT-PEAK-5980
msi_url (direct): https://rmm.azcomputerguru.com/sites/3b20ef97-c764-4ef8-9154-79c3d5b486f8/installer

Vault file: D:/vault/clients/birthbiologic/gururmm-site-main.sops.yaml

2. MSI Build Fix — "MSI build on Pluto failed"

Symptom: Clicking "Download MSI" in the GuruRMM dashboard for any site returned "MSI build on Pluto failed" in red.

Diagnosis: Server log showed:

stdout=C:\gururmm\installer\gururmm-agent.wxs(226) : error WIX0094:
The identifier 'Binary:Wix4UtilCA_X64' could not be found.

Root cause: The build_site_msi_on_pluto function in server/src/api/install.rs was calling wix build without -ext WixToolset.Util.wixext. The InstallReportCA custom action uses BinaryRef="Wix4UtilCA_X64" which lives in the Util extension. The base-MSI build in build-agents.sh had the flag; the on-demand per-site build did not.

Fix: Added -ext WixToolset.Util.wixext to the WiX command in build_site_msi_on_pluto:

"cd C:\\gururmm\\installer && wix.exe build gururmm-agent.wxs \
 -arch x64 -d Version={version} -d SITEKEY={site_id} \
 -o {remote_out} -ext WixToolset.Util.wixext"

Applied directly on Jupiter via sed -i, rebuilt server (cargo build --release in server/), restarted gururmm-server. Then committed and pushed the fix to Gitea.

Fix commit: 6106087 — "fix: add WixToolset.Util.wixext to site MSI build command"

Note: This was a discrepancy between build-agents.sh (had the flag) and install.rs (didn't). Added to DESIGN.md as a documented rule.

3. DESIGN.md — GuruRMM Design Guide Created

Created docs/DESIGN.md in the GuruRMM repo. This is a new document capturing per-component design decisions and hard constraints that were previously scattered across session logs and verbal decisions.

Committed: 6b76dd7 — "docs: add DESIGN.md — per-component architectural decisions and rules"

Sections:

  • Project-Wide Rules (no TOML/config for endpoints, registry as source of truth)
  • Agent (auto-install, per-agent enrollment keys, legacy OS support, .old cleanup, downgrade guard)
  • Installer/MSI (WiX v4 only, Pluto-only, required extension, Wait="no" rationale, install-report CA as debug logger, no UI extension)
  • Build Pipeline (webhook-only builds, parallelism, signing, toolchain self-bootstrapping, build lock)
  • Server (PostgreSQL not MariaDB, INET sqlx pattern, ConnectInfo extractor, stop-before-replace, migration recording)
  • Dashboard (useMemo pitfall, sidebar colors, modal key reset, theme support)
  • Tray Application (separate crate, user session, policy-controlled, named pipe IPC)
  • Protocol / Wire Format (WebSocket message types, heartbeat)

Files Created / Modified

File Change
D:/vault/clients/birthbiologic/gururmm-site-main.sops.yaml Created (encrypted vault entry for BirthBiologic RMM site)
/home/guru/gururmm/server/src/api/install.rs Added -ext WixToolset.Util.wixext to Pluto WiX build command
docs/DESIGN.md (in gururmm repo) Created — comprehensive design guide

Commits (gururmm repo)

SHA Message
6106087 fix: add WixToolset.Util.wixext to site MSI build command
6b76dd7 docs: add DESIGN.md — per-component architectural decisions and rules

Update: 19:25 UTC — MSI Still Failing, Root Cause Found and Fixed

Problem

After the earlier install.rs fix and server rebuild, MSI generation was still failing with the same WIX0094 error.

Root Cause

Two compounding issues:

1. Wrong binary deployed. The gururmm-server service runs from /opt/gururmm/gururmm-server, not /usr/local/bin/gururmm-server. The rebuild at 17:53 placed the new binary in /home/guru/gururmm/server/target/release/gururmm-server but it was never copied to /opt/gururmm/. The old binary (from 2026-04-20 18:32) kept running.

ExecStart=/opt/gururmm/gururmm-server   ← service path
/usr/local/bin/gururmm-server            ← wrong path (stale, Apr 20)
/home/guru/gururmm/server/target/release/gururmm-server  ← new binary (never deployed)

2. Migration 013 not registered. Once the correct binary was deployed and the service restarted, it crashed immediately on startup:

Error: while executing migration 13: error returned from database:
relation "install_reports" already exists

Migration 013 (install_reports table) had been applied to the DB in a prior session but never recorded in _sqlx_migrations. sqlx tried to re-run it, hit the conflict, and crashed.

Fix

  1. Deployed the correct binary:

    sudo systemctl stop gururmm-server
sudo cp /home/guru/gururmm/server/target/release/gururmm-server /opt/gururmm/gururmm-server

  2. Registered migration 013 in _sqlx_migrations:

    INSERT INTO _sqlx_migrations (version, description, installed_on, success, checksum, execution_time)
VALUES (
  13,
  'install reports',
  NOW(),
  true,
  decode('76d53ea1c51f9ce70c01f5b8b545d17f63eab5b2c447e880cdb1f25807ed30c626df818aadea6db9d024cdf2e72d3062', 'hex'),
  0
);

    Checksum was computed via hashlib.sha384 of the migration file contents.

  3. Restarted service — came up clean, agents reconnected.

Lesson

Always deploy to /opt/gururmm/gururmm-server — that is the path in the systemd ExecStart. /usr/local/bin/gururmm-server is a stale copy from early setup and is not used. This should be added to CONTEXT.md / DESIGN.md anti-patterns.

Pending / Next Tasks

From previous session (still pending):

  • Test MSI installer on BirthBiologic server — install via https://rmm.azcomputerguru.com/install/BRIGHT-PEAK-5980 or MSI from dashboard
  • Consent tenant-admin and user-manager apps in BirthBiologic tenant (only investigator consented so far)
  • BirthBiologic Datto → SharePoint migration script (PowerShell, tenant-admin Graph API, app-only auth, reads Datto Workplace local file server, uploads to SharePoint via Sites.ReadWrite.All)
  • mvaninc CA policy — create policy requiring MFA for all sign-ins (Mike to do in portal, not scriptable)
  • Legacy build deployment — still needs first trigger via webhook push to produce legacy binaries

Infrastructure

Component Location Notes
GuruRMM server guru@172.16.3.30 gururmm-server service
Pluto build VM Administrator@172.16.3.36 Windows MSVC + WiX
Downloads dir /var/www/gururmm/downloads/ binaries, MSIs
Build log /var/log/gururmm-build.log
Vault D:/vault/ SOPS AGE-encrypted

Credentials

  • PostgreSQL (gururmm): gururmm / 43617ebf7eb242e814ca9988cc4df5ad @ 172.16.3.30:5432/gururmm
  • Build server SSH: guru@172.16.3.30
  • Pluto SSH: Administrator@172.16.3.36
  • Webhook secret: gururmm-build-secret
  • Gitea internal API: http://172.16.3.20:3000
  • BirthBiologic RMM site: api_key grmm_1ZB1qV9Q61b9Noq8BIaZGwLNjZMfF49i (also in vault)

Update: 21:30 UTC — Cleanup EXE, Debug Agent, BB-SERVER MSI Troubleshooting

Context

Continuing from the previous compacted conversation. All work in this update is in the GuruRMM project (gururmm repo on Jupiter, local copy at D:\claudetools\projects\msp-tools\guru-rmm).

1. Cleanup EXE Deployment

Resumed deploying gururmm-cleanup.exe to Jupiter. Method used: base64-encode the EXE on Pluto via RMM agent command, capture the output, decode locally, SCP to Jupiter.

Pluto agent ID: 5316f56f-a1b3-4ac5-97ac-71ddf6a74d2e

JWT generation (Pluto admin user):

import json, base64, hmac, hashlib, time
secret_bytes = 'ZNzGxghru2XUdBVlaf2G2L1YUBVcl5xH0lr/Gpf/QmE='.encode('utf-8')
# User sub: 490e2d0f-067d-4130-98fd-83f06ed0b932 (admin@azcomputerguru.com)

SCP to Pluto failed (SYSTEM account has no SSH private key at C:\Windows\System32\config\systemprofile\.ssh\). Fell back to base64-through-agent approach.

Base64 command sent to Pluto:

[Convert]::ToBase64String([IO.File]::ReadAllBytes('C:/gururmm/agent/target/debug-agent/release/gururmm-agent.exe'))

File size: 3.8 MB (3,948,544 bytes). B64 length: 5,264,728 chars.

Decode locally and SCP to Jupiter:

py -c "import base64; ..."   # decode to D:/tmp/gururmm-agent-debug.exe
scp D:/tmp/gururmm-agent-debug.exe guru@172.16.3.30:/tmp/gururmm-agent-debug.exe
ssh guru@172.16.3.30 'sudo cp /tmp/gururmm-agent-debug.exe /var/www/gururmm/downloads/gururmm-agent-debug.exe'

Result: /var/www/gururmm/downloads/gururmm-agent-debug.exe deployed (3.8 MB). http://172.16.3.30:3001/install/debug/download → HTTP 200 (3,948,544 bytes). ✓

Note: Cloudflare challenges https://rmm.azcomputerguru.com/install/debug/download for non-browser requests — this is expected/normal. Browser downloads work fine.

Note on cleanup.exe: Not yet built. The gururmm-cleanup.exe will be produced automatically by build-agents.sh on the next triggered build. The server route /install/cleanup/download/exe returns 503 until that first build completes.

2. Pluto's SSH Public Key (for future reference)

Pluto SYSTEM account does NOT have id_ed25519. The pubkey retrieved earlier (system@PLUTO) was incorrect or from a different context.

Pluto's SYSTEM .ssh dir contains only known_hosts (94 bytes).

Jupiter's authorized_keys was updated to add Pluto pubkey:

ssh-ed25519 AAAAC3NzaC1lZDI1NTE5AAAAIFWaMV0U3WZG3kuts7mqVaF9SN0TsKqPAC37GdVGbq0Y system@PLUTO

(Added to /home/guru/.ssh/authorized_keys — may be irrelevant since SYSTEM has no private key.)

3. Debug Agent Feature — build-agents.sh and Server Routes

Already committed in prior session:

  • build-agents.sh: added --features debug-agent --target-dir target\debug-agent to Pluto SSH build command + SCP + deploy block
  • agent/Cargo.toml: added debug-agent = [] feature
  • agent/src/service.rs: cfg-gated SERVICE_NAME, SERVICE_DISPLAY_NAME, INSTALL_DIR, CONFIG_DIR constants
  • agent/src/registry.rs: REGISTRY_KEY = SOFTWARE\GuruRMM-Debug when feature enabled
  • agent/src/device_id.rs: stores device ID in C:\ProgramData\GuruRMM-Debug\.device-id
  • agent/src/updater/mod.rs: detect_binary_path() and detect_config_dir() use debug paths
  • server/src/main.rs on Jupiter: routes for /install/debug/download and cleanup endpoints
  • server/src/api/install.rs on Jupiter: download_debug_exe() handler

4. GuruRMM Debug Site Created

Created a new site for the debug agent to enroll into:

Field Value
Site ID d6b8233a-6cc1-4a44-888d-01ee49123fba
Site name GuruRMM Debug
Site code BOLD-HARBOR-1855
API key grmm_mm2DnrF6kt9Ml8AyJCuHJJHnBTyXHX_4
Client AZ Computer Guru (417420f4-c3f4-482a-acd4-d6f63c8cddde)

Issue identified: The debug agent currently prompts for a site code on first run because:

  1. No config file exists
  2. No site code embedded in the binary

Fix needed (not yet done): Hardcode the debug site API key into the debug-agent feature using a cfg-gated constant. Or embed it at build time. This would allow the debug EXE to auto-install silently without prompting.

Current workaround: User entered BRIGHT-PEAK-5980 (BirthBiologic) when prompted.

5. BB-SERVER Connected

Debug agent installed on BB-SERVER (BirthBiologic's server) and is now online in the RMM.

Field Value
Agent ID 6c02baa7-0f1c-4990-b466-c9ab9eaefd3b
Hostname BB-SERVER
OS Windows Server 2016 (build 14393)
Agent version 0.6.2
Site BirthBiologic Main Office (3b20ef97-c764-4ef8-9154-79c3d5b486f8)
Status online

6. MSI Installer Troubleshooting via BB-SERVER

Using BB-SERVER's debug agent to test the MSI installer and capture verbose logs.

Problem 1 — Cloudflare blocks non-browser downloads:

  • Invoke-WebRequest without a browser UA gets Cloudflare's JS challenge page instead of the MSI
  • Fix: pass -UserAgent 'Mozilla/5.0 ...' to Invoke-WebRequest

Problem 2 — msiexec doesn't accept forward slashes:

  • Error 2203 "Cannot open database file" with C:/grmm.msi
  • Fix: use C:\\grmm.msi (JSON-escaped backslash)

Working command format:

Invoke-WebRequest -Uri '...' -OutFile C:\\grmm.msi -UserAgent $ua -UseBasicParsing;
msiexec /i C:\\grmm.msi /quiet /l*v C:\\grmm.log;
Get-Content C:\\grmm.log -Tail 100

Command in flight (cmd ID fa68659e-3395-48a2-adee-9624dfd40cd7) — still running as of session save. Check with:

curl -s "http://172.16.3.30:3001/api/commands/fa68659e-3395-48a2-adee-9624dfd40cd7" \
  -H "Authorization: Bearer <JWT>"

7. RMM API — Correct Endpoints

Operation Endpoint
Send command POST http://172.16.3.30:3001/api/agents/:id/command
Get command status GET http://172.16.3.30:3001/api/commands/:id
List agents GET http://172.16.3.30:3001/api/agents
Get site install info GET http://172.16.3.30:3001/api/sites/:id/install-info
Download site MSI (auth) GET http://172.16.3.30:3001/api/sites/:id/installer
Download site MSI (public) GET https://rmm.azcomputerguru.com/install/BRIGHT-PEAK-5980/download/msi

JWT generation for API calls:

  • Secret (raw bytes): ZNzGxghru2XUdBVlaf2G2L1YUBVcl5xH0lr/Gpf/QmE=
  • Admin user sub: 490e2d0f-067d-4130-98fd-83f06ed0b932 (admin@azcomputerguru.com)
  • Claims: sub, role: "admin", orgs: [], exp: now+3600, iat: now
  • Algorithm: HS256, key = secret string encoded as UTF-8 bytes (NOT base64-decoded)

Known user IDs:

490e2d0f-067d-4130-98fd-83f06ed0b932  admin@azcomputerguru.com   (admin)
4d754f36-0763-4f35-9aa2-0b98bbcdb309  claude-api@azcomputerguru.com (admin)
294c1242-68ac-42e7-85b0-564c8b155dba  howard@azcomputerguru.com  (admin)

8. JSON Escaping Issue with Agent Commands

The RMM server's serde_json is strict about JSON escape sequences. Commands containing \" embedded double-quotes cause "invalid escape" errors when passed via --data-binary @file from curl if there are edge cases.

Working approach: Use shell single-quote wrapping with '"'"' technique for embedded single-quoted PowerShell strings in the curl -d argument. Avoids file escaping entirely.

Key rules:

  • Never use \g, \L, \D, etc. — only valid JSON escapes: \\, \", \/, \b, \f, \n, \r, \t, \uXXXX
  • Forward slashes are fine in JSON strings
  • Backslashes in PowerShell paths need \\ in JSON (gives \ in the actual string)

Pending Tasks

Task Status Notes
Cleanup EXE on Pluto Pending Needs first build trigger. Route ready, will 503 until built.
Debug agent auto-install Not done Needs hardcoded debug site key in debug-agent feature
MSI 2762 test on BB-SERVER In progress Command running, awaiting result
BirthBiologic — MSI verified working Pending Testing now
BirthBiologic — consent tenant-admin/user-manager Pending
BirthBiologic — Datto→SharePoint migration script Pending
mvaninc CA policy (MFA) Pending Mike to do manually in portal
Remote uninstall feature Pending New WS message + server DELETE endpoint + dashboard button

Infrastructure Additions This Update

Item Value
Debug site BOLD-HARBOR-1855, api_key grmm_mm2DnrF6kt9Ml8AyJCuHJJHnBTyXHX_4
BB-SERVER agent ID 6c02baa7-..., online, BirthBiologic Main Office
Debug EXE /var/www/gururmm/downloads/gururmm-agent-debug.exe (3.8 MB)
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