# Session Log - Gemini CLI Install + Wolkin RMM Diagnostic + Remote Printing Planning

## User
- **User:** Mike Swanson (mike)
- **Machine:** Mikes-MacBook-Air (Mac)
- **Role:** admin

## Date
2026-06-06

## Summary

Installed Google Gemini CLI on Mac as second fleet host for AGY skill, fixed macOS compatibility issue in GuruRMM onboarding diagnostic script, ran comprehensive security/health diagnostic on Wolkin's FRONT machine (AMBER grade - 5 warnings including tamper protection disabled and pending updates), dispatched reboot to clear pending reboot flag, and documented Tailscale mesh VPN solution for remote laptop printing to office printer.

## Context

Following the recent addition of the AGY skill (Google Gemini CLI router for second-opinion verification and code review), needed to expand Gemini CLI availability beyond GURU-5070 to the Mac. Wolkin client needed RMM system health assessment and has an upcoming requirement for remote printing without traditional VPN infrastructure.

## Work Performed

### 1. Gemini CLI Installation and Configuration

**Objective:** Install and configure Google Gemini CLI on Mac to serve as second fleet host for AGY skill capabilities.

**Steps:**

1. **Read AGY skill documentation** - Reviewed `.claude/skills/agy/SKILL.md` to understand installation requirements and configuration structure

2. **Verified npm availability** - Confirmed npm 11.6.2 installed via Homebrew at `/opt/homebrew/bin/npm`

3. **Installed Gemini CLI globally:**
   ```bash
   npm install -g @google/gemini-cli
   ```
   - Installed successfully in 4 seconds
   - Version: 0.45.1
   - Binary location: `/opt/homebrew/bin/gemini`

4. **Updated identity.json** - Added Gemini configuration block to `.claude/identity.json`:
   ```json
   "gemini": {
     "installed": true,
     "binary": "/opt/homebrew/bin/gemini",
     "auth": "oauth",
     "is_fleet_host": true,
     "capabilities": [
       "text",
       "verify",
       "review",
       "review-files",
       "review-diff",
       "image-analyze",
       "search"
     ]
   }
   ```

5. **Documented next step:** User needs to run `gemini` interactively once to complete Google OAuth login. Credentials will be stored at `~/.gemini/oauth_creds.json`.

**Outcome:** Mac is now configured as a Gemini CLI fleet host alongside GURU-5070. All AGY skill modes (text, verify, review, image-analyze, search) are available once OAuth is completed.

**Technical Note:** Gemini uses Google OAuth (no API key required), supports vision input and live web search in keyless mode, and provides genuinely independent second-model verification for Claude's findings.

---

### 2. Repository Synchronization (2 cycles)

**First Sync (12:12 UTC):**
- Pulled 15 commits (12 Mike, 3 Howard)
- Key additions: AGY skill, Mailprotector skill, M365 remediation updates, CDP Chrome driver script
- Wiki updates: Cascades Tucson client article, index
- Vault: 2 commits (Cascades sysadmin password rotation, Mailprotector API key)

**Second Sync (16:03 UTC):**
- Pulled 17 commits (13 Mike, 4 Howard)
- Major updates:
  - Sync infrastructure: sync-lock.sh for per-machine locking, prevents concurrent sync conflicts
  - human-flow skill: AST-based scanner v2 with Friction Index rubric, "elevate (polish & redesign)" heuristics
  - Radio show website: keyboard accessibility improvements (skip link, focus-visible, mobile menu)
  - Cascades Tucson: Multiple GPO scripts (caregiver lockdown, device lockdown, SCP config)
  - New wiki article: IX server (233 lines) - full hosting server inventory
  - Memory feedback: AGY review not read-only, verify committed state before push
- Global commands updated: checkpoint.md, save.md, scc.md, sync.md

**Identity.json warning noted:** Machine name shows 'Mikes-MacBook-Air' but hostname resolves to 'Mac' - discrepancy should be corrected for proper attribution.

---

### 3. Wolkin RMM Health Diagnostic

**Objective:** Run comprehensive onboarding security and health diagnostic on Wolkin's office PC to establish baseline and identify issues.

**Agent Resolution:**
- Client: Wolkin, Robert
- Hostname: front
- Agent ID: `877d311a-4b24-462c-97b1-d2a0f7730a71`
- OS: Windows 11 Home 25H2 (build 26200)
- Hardware: ASUS P500MV, Intel i5-13420H (8c/12t), 15.6GB RAM
- Last seen: 2026-06-06 13:29 UTC (online)

**Diagnostic Script Issue Discovered:**

Encountered macOS/Linux compatibility issue in `run-onboarding-diagnostic.sh` line 221:
```bash
base64 -w0 "$PROBE" > "$B64_FILE"  # GNU flag, fails on BSD/macOS
```

**Fix applied:**
```bash
# macOS (BSD) base64 uses -i for input file and has no line-wrap flag.
# GNU base64 accepts file as positional arg and uses -w0 for no wrap.
if base64 -i "$PROBE" > "$B64_FILE" 2>/dev/null; then
    : # macOS/BSD path succeeded
elif base64 -w0 "$PROBE" > "$B64_FILE" 2>/dev/null; then
    : # GNU path succeeded
else
    # Fallback: stdin input, strip newlines
    base64 < "$PROBE" | tr -d '\n' > "$B64_FILE"
fi
```

This fix makes the script portable across macOS (BSD base64) and Linux (GNU base64).

**Diagnostic Execution:**

- Probe size: 70,739 bytes → chunked into 4 x 24KB base64-encoded uploads
- Dispatched via RMM API, executed as SYSTEM context on endpoint
- Timeout: 240 seconds
- Result: Completed successfully, exit code 0
- JSON output: 17,509 bytes extracted from fenced markers

**Grade: AMBER**
- 0 critical findings
- 5 warning findings
- 14 info findings
- 0 unknown (all checks executed successfully)

**WARNING Findings (Priority Issues):**

1. **Defender Tamper Protection OFF** (`sec.defender.tamper_off`)
   - Impact: Malware or local admin can silently disable Defender
   - Current state: RTP enabled, service running, signatures current (0 days old), but tamper protection disabled
   - Recommendation: Enable via Intune/Security Center

2. **4 Pending Windows Updates** (`sec.patch.pending`)
   - May include security patches
   - Recommendation: Install during next maintenance window

3. **Stability Events - 2 Disk Errors** (`health.stability.some`)
   - Event IDs 7/51/153 (disk errors) detected in last 14 days
   - 0 unexpected shutdowns, 0 BSODs
   - Recommendation: Run Check Disk or SMART diagnostics to assess disk health

4. **Reboot Pending** (`health.reboot_uptime.pending`)
   - Flag: PendingFileRenameOperations
   - Impact: Blocks patch installation, leaves system in half-updated state
   - Recommendation: Schedule restart (dispatched during this session)

5. **6 Auto-Start Services Not Running** (`health.failed_services.stopped`)
   - Dropbox Updater services (2) - benign
   - Google Updater services (2) - benign
   - **Group Policy Client (gpsvc)** - notable, should run even on workgroup machines
   - Intel Platform License Manager - benign
   - Recommendation: Investigate Group Policy Client status

**POSITIVE Findings (Security/Health):**

- [OK] BitLocker enabled on OS volume with TPM + recovery password protector (100% encrypted)
- [OK] Defender active: RTP on, service running, signatures current
- [OK] Only Defender registered as AV (no conflicts)
- [OK] All firewall profiles enabled (Domain, Private, Public)
- [OK] No competitor/leftover RMM agents detected
- [OK] ScreenConnect client present (expected ACG tooling)
- [OK] SMBv1 disabled
- [OK] LAPS detected
- [OK] OS build in support until 2027-10-12
- [OK] Last hotfix: KB5089573 (2026-05-27)

**Inventory Baseline:**

- Manufacturer: ASUSTeK COMPUTER INC.
- Model: ASUS P500MV_V500MVC
- Serial: T7PFAG00B454281
- CPU: Intel i5-13420H (8 cores, 12 logical)
- RAM: 15.6 GB
- BIOS: P500MV.324 (2025-06-23)
- Chassis: Desktop (not laptop)
- TPM: Present / Secure Boot: Enabled
- Domain: Workgroup (not domain-joined)
- OS Activation: Licensed
- Uptime: 10.2 days
- Storage: C: drive 534.7 GB free of 930.6 GB (57.5% free)
- Network: Intel I219-V @ 192.168.1.153 (DHCP)
- Installed software: 29 packages
- Scheduled tasks (non-MS, enabled): 22
- Local administrators: FRONT\Administrator, FRONT\Localadmin, FRONT\Owner

**Baselines Written:**
- JSON (immutable snapshot): `clients/rswolkin/onboarding-baselines/FRONT-20260606T133142.json`
- Markdown (human report): `clients/rswolkin/onboarding-baselines/FRONT-20260606T133142.md`

This is the first baseline for this host. Future diagnostics will diff against this to show new/resolved/regressed findings and software changes.

**Reboot Dispatched:**

To clear the pending reboot flag and allow pending updates to complete:
```powershell
Restart-Computer -Force
```
- Command ID: `c7d3a53f-a503-4136-b757-d79f18e94136`
- Status: Running (system restarted immediately)
- Alert posted to #dev-alerts: `[RMM] Mike dispatched reboot to FRONT (windows) - clear pending reboot + install updates -> cmd:c7d3a53f`

**Outcome:** Comprehensive baseline established for FRONT. Reboot will clear pending flag and allow update installation. Follow-up required for tamper protection, Group Policy Client service, and disk health assessment.

---

### 4. Remote Printing Solution - Tailscale Planning

**Requirement:** Remote laptop (not yet enrolled in RMM) needs to print to office printer. Office is on Verizon home internet (likely CGNAT, dynamic IP). No existing VPN infrastructure.

**Challenge:** Traditional VPN solutions don't work well with residential ISP CGNAT and dynamic IPs. Port forwarding not viable.

**Solution Evaluation:**

| Option | Pros | Cons | Decision |
|--------|------|------|----------|
| **Tailscale** | Works through CGNAT, free (≤100 devices), zero-config, WireGuard-based, ACG manageable via RMM | Requires client on both machines | ✓ **Selected** |
| GuruConnect | ACG-controlled, no third-party dependency | Not production-ready yet | Deferred |
| ScreenConnect Print Redirect | Already deployed, no new infrastructure | Only works office→laptop direction, not laptop→office | Won't work |
| Cloud Print (PrinterLogic, etc.) | Professional, works anywhere | Expensive ($10-30/user/month), overkill | Rejected |
| DIY VPN Server | Full control | CGNAT blocks inbound, needs static IP/DDNS, complex | Rejected |

**Selected Solution: Tailscale Mesh VPN**

**Architecture:**
1. Install Tailscale on office PC (FRONT - already in RMM)
2. Install Tailscale on remote laptop (to be enrolled in RMM)
3. Both join same tailnet (Tailscale network)
4. Share office printer from FRONT via SMB
5. Laptop adds network printer using FRONT's Tailscale IP (100.x.x.x range)

**Deployment Plan Documented:** `clients/rswolkin/remote-printing-tailscale-plan.md`

**Plan Contents:**
- Use case and requirements
- Architecture diagram (text)
- Step-by-step implementation checklist:
  1. Enroll remote laptop in GuruRMM
  2. Install Tailscale on FRONT (download from tailscale.com/download/windows)
  3. Install Tailscale on remote laptop
  4. Configure printer sharing from FRONT
  5. Add network printer on laptop via Tailscale IP
  6. Test print job
  7. Vault Tailscale credentials: `clients/rswolkin/tailscale.sops.yaml`
  8. Document printer details and Tailscale IPs
- Alternative solutions considered and rejected (with rationale)
- Follow-up task checklist

**Why Tailscale Wins:**
- Zero configuration mesh networking (no manual IP/routing setup)
- Survives network changes (DHCP, roaming, etc.)
- Peer-to-peer where possible, relay where NAT traversal fails
- Free for personal/small business use
- Can be deployed and managed via RMM scripts once laptops are enrolled
- Secure by default (WireGuard, cryptographic identity)

**Next Steps:**
1. Create Tailscale account for Wolkin (or use existing if available)
2. Enroll remote laptop in GuruRMM (generate site enrollment key)
3. Deploy Tailscale to both machines (can script via RMM)
4. Configure and test printer connectivity
5. Vault credentials and document final configuration

**Outcome:** Clear deployment path documented for remote printing without traditional VPN complexity. Solution scales to additional remote workers if needed in future.

---

## Files Modified

1. `.claude/scripts/run-onboarding-diagnostic.sh`
   - Fixed macOS base64 compatibility (BSD vs GNU flag differences)
   - Now portable across macOS and Linux

2. `.claude/identity.json`
   - Added Gemini configuration block
   - Set machine as fleet host with full AGY capabilities

## Files Created

1. `clients/rswolkin/onboarding-baselines/FRONT-20260606T133142.json`
   - Immutable diagnostic snapshot (17,509 bytes)
   - Complete system state: security, health, inventory
   - Source of truth for future diffs

2. `clients/rswolkin/onboarding-baselines/FRONT-20260606T133142.md`
   - Human-readable diagnostic report
   - Grade: AMBER (0 critical, 5 warning, 14 info)
   - Detailed findings with remediation guidance

3. `clients/rswolkin/remote-printing-tailscale-plan.md`
   - Complete Tailscale deployment plan
   - Architecture, implementation steps, alternatives evaluated
   - Follow-up task checklist

## Alerts Posted

- `[RMM] Mike dispatched reboot to FRONT (windows) - clear pending reboot + install updates -> cmd:c7d3a53f`
  - Posted to #dev-alerts (message_id: 1512812299428302908)

## Follow-up Required

### Immediate (This Week)

1. **Complete Gemini OAuth** - Run `gemini` interactively on Mac to log in with Google account

2. **Fix identity.json machine name** - Update `machine` field from "Mikes-MacBook-Air" to match actual hostname "Mac" for correct attribution

3. **Monitor FRONT reboot** - Verify system came back online after restart (expected 2-5 minutes)

### Short-term (Next 1-2 Weeks)

4. **Address FRONT AMBER findings:**
   - Enable Defender tamper protection (via Intune/Security Center or local policy)
   - Install 4 pending Windows updates (schedule maintenance window)
   - Investigate stopped Group Policy Client service (should auto-start on workgroup machines)
   - Run Check Disk or SMART diagnostics to assess disk health (2 disk errors detected)

5. **Deploy Tailscale remote printing solution:**
   - Create/confirm Tailscale account for Wolkin
   - Enroll remote laptop in GuruRMM (generate site enrollment key)
   - Deploy Tailscale to FRONT and laptop
   - Configure printer sharing from FRONT
   - Test remote print job end-to-end
   - Vault Tailscale credentials: `clients/rswolkin/tailscale.sops.yaml`
   - Document printer make/model/share name and Tailscale IPs

6. **Re-run diagnostic after remediation** - Establish second baseline showing improvements

## Technical Notes

### macOS base64 Compatibility

BSD base64 (macOS) vs GNU base64 (Linux) syntax differences:

```bash
# BSD (macOS) - uses -i flag for input file, no line wrapping by default
base64 -i input.txt > output.b64

# GNU (Linux) - accepts file as positional arg, uses -w0 to disable line wrapping
base64 -w0 input.txt > output.b64

# Portable fallback - stdin input with newline stripping
base64 < input.txt | tr -d '\n' > output.b64
```

The diagnostic script now tries BSD first, falls back to GNU, then uses portable stdin method if both fail. This ensures compatibility across all fleet machines.

### GuruRMM Onboarding Diagnostic

- Probe size: ~70KB PowerShell script
- Uploaded in 24KB base64-encoded chunks to stay under agent command body limit (~32-40KB)
- Executes as SYSTEM context
- Output: JSON fenced between `===DIAG-JSON-START===` and `===DIAG-JSON-END===` markers
- Grading: RED (≥1 critical), AMBER (≥1 warning, 0 critical), GREEN (0 critical, 0 warning)
- Checks: Defender state, AV conflicts, foreign RMM agents, firewall, BitLocker, local admins, patch posture, OS EOL, RDP/NLA, SMBv1, UAC, LAPS, disk health, stability, services, domain channel, time source, battery (laptops), backup agent
- Inventory: hardware/BIOS, OS details, installed software, network, scheduled tasks, autoruns
- Baselines immutable and append-only; diffs show changes between runs

### Tailscale Architecture

- Mesh VPN using WireGuard protocol
- Coordination server (Tailscale's) handles NAT traversal and key exchange
- Peer-to-peer connections where possible; relay (DERP servers) when direct fails
- Each device gets stable 100.x.x.x IP that persists across networks
- Access control via ACLs (can restrict which devices talk to which)
- Works through CGNAT without port forwarding or static IPs
- Free tier: up to 100 devices, 1 admin, community support
- Paid tier ($6/user/month): multiple admins, SSO, device approval, audit logs

For Wolkin's use case (2 devices, simple printer sharing), free tier is sufficient.

## Session Metadata

- **Duration:** ~2 hours
- **Mode:** General → Client (Wolkin)
- **Primary tools:** RMM skill, Bash, Read, Edit, Write
- **Commits:** 1 fix (base64 compatibility), 1 config (Gemini), 3 new files (baselines + plan)
- **RMM commands dispatched:** 1 (reboot to FRONT)

---

**Session complete.** Gemini CLI operational on Mac (pending OAuth), Wolkin FRONT system baselined and rebooting, remote printing solution documented and ready for deployment.
