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claudetools/clients/rswolkin/remote-printing-tailscale-plan.md
Mike Swanson 60394a803e sync: auto-sync from Mikes-MacBook-Air.local at 2026-06-06 06:47:07
Author: Mike Swanson
Machine: Mikes-MacBook-Air.local
Timestamp: 2026-06-06 06:47:07
2026-06-06 06:47:08 -07:00

2.8 KiB

Wolkin Remote Printing - Tailscale Solution

Date: 2026-06-06 Status: Pending deployment Decision: Use Tailscale mesh VPN for remote laptop → office printer connectivity

Use Case

  • Remote laptop (not yet in RMM) needs to print to office printer
  • Office network: Verizon home internet router (likely CGNAT/dynamic IP)
  • No existing VPN infrastructure
  • Single user remote printing scenario

Solution: Tailscale

Deployment targets:

  1. Office PC: FRONT (already in RMM - 877d311a-4b24-462c-97b1-d2a0f7730a71)
  2. Remote laptop: (to be enrolled in RMM)

Architecture:

  • Install Tailscale client on both machines
  • Create shared Tailscale network (tailnet)
  • Office printer shared from FRONT via SMB
  • Laptop connects to printer using FRONT's Tailscale IP

Benefits:

  • Works through CGNAT without port forwarding
  • Free for personal use (up to 100 devices)
  • Zero-config mesh networking
  • Secure (WireGuard-based)
  • ACG can manage via RMM once deployed

Implementation Steps

  1. Enroll remote laptop in GuruRMM

    • Generate enrollment key for Wolkin site
    • Install agent on laptop
    • Run onboarding diagnostic
  2. Install Tailscale on FRONT

  3. Install Tailscale on remote laptop

    • Same download/install process
    • Join same tailnet
    • Note laptop's Tailscale IP
  4. Configure printer sharing

    • Share office printer from FRONT (if not already shared)
    • On laptop: Add network printer using \\<FRONT-tailscale-IP>\<PrinterName>
    • Test print job
  5. Documentation

    • Document Tailscale credentials in vault: clients/rswolkin/tailscale.sops.yaml
    • Add printer name and share path to this doc
    • Update wiki/clients/wolkin.md (when created)

Alternative Considered

  • ScreenConnect print redirection: Wrong direction (office→laptop, not laptop→office)
  • GuruConnect: Not yet production-ready for this use case
  • Commercial cloud print: Overkill/expensive for single user
  • DIY VPN: Complex, CGNAT issues, maintenance burden

Notes

  • FRONT uptime: 10.2 days (as of 2026-06-06) - stable enough for print server role
  • FRONT has pending reboot (dispatched 2026-06-06) - Tailscale install can happen after
  • Office printer make/model: (to be documented)
  • Remote laptop specs: (to be documented after enrollment)

Follow-up Tasks

  • Create Tailscale account for Wolkin (if needed)
  • Enroll remote laptop in RMM
  • Deploy Tailscale to both machines
  • Configure printer sharing
  • Test remote print job
  • Vault Tailscale credentials
  • Document printer details

Ticket/Session reference: 2026-06-06 RMM diagnostic + remote printing planning