claudetools/session-logs/2026-04-20-mac-session.md

Session Log — 2026-04-20 (Mac)

User

• User: Mike Swanson (mike)
• Machine: Mikes-MacBook-Air.local
• Role: admin
• Mode: general

Session Summary

GuruRMM agent v0.6.1 successfully deployed to Mac with full root command execution capability. Agent authenticated and online in RMM dashboard. PROJECT_STATE.md updated with deployment details. Started Grabb & Durando user provisioning request but paused to continue on Windows desktop.

---

Work Completed

1. GuruRMM Agent Mac Deployment (v0.6.1)

Problem: Mac agent showing offline in RMM dashboard.

Investigation:

• Found stale agent entry from 2026-04-03 (crashed 4 seconds after connection)
• Agent ID: 6177bcac-e046-4166-ac76-a6db68a363ab
• Deleted from RMM database

Fresh Installation:

• Built macOS ARM64 binary (3.2 MB): cargo build --release
• Installed to: /usr/local/bin/gururmm-agent
• Config: /Library/Application Support/GuruRMM/agent.toml
• LaunchDaemon: /Library/LaunchDaemons/com.azcomputerguru.gururmm.plist
• Logs: /Library/Logs/GuruRMM/agent.log and agent-error.log

Authentication Fix:

• Initial problem: Config had site_code = "SWIFT-CLOUD-6910" + api_key = "site-code-auth"
• Issue: Agent only reads api_key field from config (no site_code field in struct)
• Solution: Set api_key = "SWIFT-CLOUD-6910" (the actual site code)
• Embedded site code system only used during install command, not run command

Passwordless Sudo Configuration:

• Created /etc/sudoers.d/claudetools with passwordless rules for GuruRMM operations
• Used wildcard paths (/Library/Application*) to handle spaces in paths
• Purpose: Manual ClaudeTools operations (agent already runs as root)

Deployed Agent Details:

• Agent ID: 001d5198-7807-4d63-b46d-069c9c10ed75
• Hostname: Mikes-MacBook-Air.local
• OS: macOS 26.3.1 (Darwin ARM64)
• Version: 0.6.1
• Site: Main Office (SWIFT-CLOUD-6910)
• Status: online
• Runs as: root (no UserName key in LaunchDaemon plist)

Command Execution Test:

• Sent via RMM API: whoami && hostname && uname -a
• Result: Executed as root successfully
• Exit code: 0
• Duration: 61ms
• Output:

  root
  Mikes-MacBook-Air.local
  Darwin Mikes-MacBook-Air.local 25.3.0 Darwin Kernel Version 25.3.0: Wed Jan 28 20:54:55 PST 2026; root:xnu-12377.91.3~2/RELEASE_ARM64_T8132 arm64
  

Security Model:

• Agent connects once with site code authentication
• All subsequent commands execute as root without additional auth
• No per-command authorization prompts
• Anyone with RMM dashboard access to "Main Office" site can execute commands

Files Created:

• temp/setup-sudo-for-claudetools.sh - Initial bootstrap script (had sudoers syntax errors)
• temp/setup-sudo-for-claudetools-fixed.sh - Fixed version using wildcards

2. PROJECT_STATE.md Updates

Updated projects/gururmm-agent/PROJECT_STATE.md:

• Status changed: COMPLETE → ACTIVE
• Last Activity: 2026-03-31 → 2026-04-20
• Added macOS deployment summary
• Added Recent Changes table with 4 entries:
  • macOS agent v0.6.1 deployed (DEPLOYED)
  • Deleted stale agent entry (COMPLETE)
  • Fixed authentication issue (FIXED)
  • Created passwordless sudo rules (DEPLOYED)
• Added "macOS Agent Details" section with full deployment info

Commit: af31c3a Pushed to Gitea: 2026-04-20 19:45:00

3. Multiple Sync Operations

First sync (19:04):

• Pulled 10 commits from Windows desktop
• PROJECT_STATE.md system rollout (29 files created)
• GuruRMM submodule updated to v0.6.2
• Ollama Tier 0 routing added

Second sync (19:34):

• Pushed sudo scripts and submodule pointer update
• Commit: 94585fe

Third sync (20:42):

• Pulled 2 commits from Windows desktop
• Extended session log with PROJECT_STATE documentation

Fourth sync (05:43 next morning):

• Encountered submodule merge conflict (Mac vs Howard's laptop)
• Mac pointed to: 69ed647 (log upload feature)
• Howard pointed to: 81eecdd
• Resolved by taking latest origin/main: b91ac5e (parallel build improvements)
• Merged Howard's Cascades Tucson Intune MDM work
• Commit: 8944432

4. Grabb & Durando User Provisioning Request

Client: Grabb & Durando (grabblaw.com) Request date: 2026-04-21 (originally showed 2016 - typo)

New user details:

• Name: Svetlana Larionova
• Email: slarionova@grabblaw.com
• Start date: Tuesday, April 22, 2026 (tomorrow)
• Computer: Whatever Parker was using
• Needs: Outlook email + computer login

M365 Access Found:

• Admin: sysadmin@grabblaw.com
• Password: r3tr0gradE99!
• Tenant ID: 032b383e-96e4-491b-880d-3fd3295672c3

Remediation Tool Consent Attempt:

• Tried to grant consent to pull license inventory
• Consent link didn't prompt for permissions (unusual behavior)
• Direct Graph API call confirmed: service principal missing in tenant
• Error: "The client application fabb3421-8b34-484b-bc17-e46de9703418 is missing service principal in the tenant"
• Possible consent policy restrictions preventing standard flow

Status: PAUSED - will create account manually in M365 Admin Center on Windows desktop

---

Infrastructure

GuruRMM Server

• API: http://172.16.3.30:3001
• Dashboard: https://rmm.azcomputerguru.com
• Database: PostgreSQL @ 172.16.3.30:5432

Mac Agent Installation Paths

• Binary: /usr/local/bin/gururmm-agent
• Config: /Library/Application Support/GuruRMM/agent.toml
• LaunchDaemon: /Library/LaunchDaemons/com.azcomputerguru.gururmm.plist
• Logs: /Library/Logs/GuruRMM/agent.log, agent-error.log
• Sudo rules: /etc/sudoers.d/claudetools

Grabb & Durando

• Domain: grabblaw.com
• Tenant ID: 032b383e-96e4-491b-880d-3fd3295672c3
• Admin Portal: https://admin.microsoft.com
• Entra Portal: https://entra.microsoft.com
• Admin Account: sysadmin@grabblaw.com / r3tr0gradE99!
• PROJECT_STATE: clients/grabb-durando/PROJECT_STATE.md (STALLED - website migration)

---

Pending Tasks

Grabb & Durando User Provisioning (TO CONTINUE ON WINDOWS)

What needs to be done:

1. Sign in to https://admin.microsoft.com as sysadmin@grabblaw.com
2. Navigate to Users > Active users > Add a user
3. Create user:
   • First name: Svetlana
   • Last name: Larionova
   • Username: slarionova@grabblaw.com
   • Password: (auto-generate or set temporary)
   • Assign appropriate license (need to check what's available)
4. Determine computer setup:
   • Azure AD joined (modern) - just sign in with M365 account
   • On-prem AD (legacy) - need to create separate AD account
   • Hybrid - create in on-prem AD, wait for sync
5. Configure computer login on "Parker's computer":
   • Need computer name/hostname
   • Need domain info (if on-prem AD)

Questions to answer:

• What M365 licenses are available in the tenant?
• What type of computer setup do they have? (Azure AD / On-prem AD / Hybrid)
• What's the computer name that Parker was using?
• Does she need any special folder/file permissions?

Reference for computer login:

• Azure AD joined: Sign in directly with slarionova@grabblaw.com
• On-prem AD: Need domain admin access to create/modify AD user
• Hybrid: Create in AD, wait for Azure AD Connect sync (typically 30 min)

---

Technical Notes

GuruRMM Agent Authentication Flow

1. Agent loads config from TOML file
2. Reads api_key field (this is actually the site code for auto-registration)
3. Connects to WebSocket: wss://rmm-api.azcomputerguru.com/ws
4. Sends Auth message with api_key, device_id, hostname, OS info
5. Server validates site code and auto-registers agent to site
6. Returns AuthAck with agent_id
7. Agent maintains persistent WebSocket connection
8. Server can send Command messages at any time
9. Agent executes commands using shell (sh -c on Mac/Linux, cmd /C on Windows)
10. Commands inherit agent's privileges (root on Mac LaunchDaemon)

Embedded Site Code System

• Purpose: Allow pre-configured agent downloads with site code embedded
• Format: Binary trailer appended to agent executable
• Structure: [site_code][4-byte LE u32 length][8-byte magic "GRMM_CFG"]
• Used during: install command only
• At runtime: Agent reads api_key from config file, NOT from embedded trailer
• For Mac deployment: Manual config file creation was simpler than embedding

macOS LaunchDaemon Privileges

• No UserName key = runs as root
• RunAtLoad = starts on boot
• KeepAlive = restarts if crashes
• Standard output/error to log files
• ProgramArguments order matters: --config must come before run subcommand

PROJECT_STATE.md Protocol

• Mandatory for any project with PROJECT_STATE.md file
• Read before acting, claim lock, perform action, release lock + log changes
• Stale lock rule: >2 hours without update = abandoned, can be cleared
• Actions requiring locks: code changes, git commits, SSH commands, DB changes, builds
• Reading/planning does NOT require locks

---

Credentials Used

1Password Items:

• GuruRMM Dashboard (Projects vault): admin@azcomputerguru.com / GuruRMM2025
• Claude-MSP-Access (Graph API) (MSP Tools vault): fabb3421-8b34-484b-bc17-e46de9703418 / [client secret]
• Grabb & Durando Data Site (Clients vault): sysadmin@grabblaw.com / r3tr0gradE99!

From session logs (2026-03-31):

• Grabblaw M365 admin: sysadmin@grabblaw.com / r3tr0gradE99!

---

Files Modified/Created

Created:

• temp/setup-sudo-for-claudetools.sh
• temp/setup-sudo-for-claudetools-fixed.sh
• /Library/Application Support/GuruRMM/agent.toml
• /Library/LaunchDaemons/com.azcomputerguru.gururmm.plist
• /etc/sudoers.d/claudetools

Modified:

• projects/gururmm-agent/PROJECT_STATE.md (status, recent changes, deployment details)
• projects/msp-tools/guru-rmm (submodule pointer: 69ed647 → b91ac5e)

Installed:

• /usr/local/bin/gururmm-agent (3.2 MB ARM64 binary)

---

Git Commits

1. 94585fe - sync: auto-sync from Mikes-MacBook-Air.local at 2026-04-19 19:34:27

   • GuruRMM submodule pointer updated
   • 2 sudo bootstrap scripts added

2. af31c3a - docs: update GuruRMM agent PROJECT_STATE with Mac deployment (v0.6.1)

   • PROJECT_STATE.md updated with full deployment details
   • Recent changes table added
   • macOS agent details documented

3. 8944432 - merge: sync from Howard's laptop - Cascades Intune MDM work + submodule update

   • Resolved submodule conflict (took b91ac5e from origin/main)
   • Merged Howard's Cascades Tucson work
   • New session log: 2026-04-20-howard-intune-mdm-prereqs-and-enrollment-profile.md

---

Next Steps (for Windows desktop session)

1. Complete Grabb & Durando user provisioning:

   • Create slarionova@grabblaw.com in M365 Admin Center
   • Check available licenses and assign appropriate one
   • Determine computer infrastructure (Azure AD vs On-prem AD)
   • Configure computer login for "Parker's computer"
   • Test: Verify user can sign in to Outlook and computer

2. Optional: Troubleshoot Grabb & Durando consent issue:

   • Check tenant consent policies in Entra portal
   • Determine why consent flow isn't showing permissions prompt
   • Consider PowerShell-based service principal installation if needed
   • Document findings in client PROJECT_STATE.md

3. Update Grabb & Durando PROJECT_STATE.md:

   • Change status from STALLED to ACTIVE
   • Add infrastructure details (M365 tenant, admin credentials reference)
   • Log this user provisioning work in Recent Changes
   • Add any discovered information about their setup

---

Context for Next Session

Current situation:

• Mac GuruRMM agent is fully deployed and operational
• RMM can now execute root commands on this Mac via dashboard
• Received urgent user provisioning request for Grabb & Durando
• Need to create Svetlana Larionova's account by tomorrow (April 22)
• Consent link for remediation tool had issues, will create account manually
• User wants to continue this work on Windows desktop (easier for M365 admin tasks)

Why switching machines:

• M365 Admin Center works better on Windows browsers
• Likely has saved sessions/credentials for M365 portals
• May have PowerShell modules installed if needed

What's ready:

• Admin credentials confirmed: sysadmin@grabblaw.com / r3tr0gradE99!
• Tenant ID confirmed: 032b383e-96e4-491b-880d-3fd3295672c3
• New user details documented above
• Start date is tomorrow - this is time-sensitive

Session log location: session-logs/2026-04-20-mac-session.md