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Tailscale Setup Guide

Tailscale creates a secure mesh VPN between Mac-Studio and MacBookPro, enabling connectivity from anywhere.

Why Tailscale?

  • Works anywhere: Connect to Mac-Studio from coffee shop, office, or home
  • No port forwarding: Works through NAT and firewalls
  • MagicDNS: Use simple hostnames (mac-studio, macbook-pro) instead of IP addresses
  • Automatic reconnection: Handles network changes gracefully

Installation

Mac App Store (Recommended)

  1. Open Mac App Store
  2. Search for "Tailscale"
  3. Install and open
  4. Sign in (use same account on both machines)

Homebrew (Alternative)

brew install --cask tailscale

Note: The CLI-only install (brew install tailscale) requires manual daemon management. The Mac App Store or cask version handles this automatically.

Setup Steps

Step 1: Install on Both Machines

Install Tailscale on Mac-Studio and MacBookPro using the same method.

Step 2: Sign In

Sign in with the same identity provider (GitHub, Google, Apple, etc.) on both machines.

Step 3: Verify Connection

# Check Tailscale status
tailscale status

# Should show both machines, e.g.:
# 100.x.x.x   mac-studio       traviscarter@  macOS   -
# 100.y.y.y   macbook-pro      traviscarter@  macOS   -

Step 4: Test Connectivity

# From Mac-Studio
tailscale ping macbook-pro

# From MacBook Pro
tailscale ping mac-studio

MagicDNS Hostnames

Tailscale automatically assigns DNS names based on your machine hostname:

Machine Tailscale Hostname
Mac Studio mac-studio
MacBook Pro macbook-pro

These hostnames work from anywhere in your Tailscale network.

SSH Configuration

Update ~/.ssh/config to use Tailscale hostnames for reliable connectivity:

# mac-studio (via Tailscale)
Host mac-studio
    HostName mac-studio
    User traviscarter
    AddKeysToAgent yes
    UseKeychain yes
    IdentityFile ~/.ssh/id_ed25519

# macbook-pro (via Tailscale)
Host macbook-pro
    HostName macbook-pro
    User traviscarter
    AddKeysToAgent yes
    UseKeychain yes
    IdentityFile ~/.ssh/id_ed25519

Key change: HostName now uses Tailscale MagicDNS name (e.g., mac-studio) instead of .local Bonjour name (e.g., Mac-Studio.local).

Test SSH

ssh mac-studio "hostname"
ssh macbook-pro "hostname"

Workflow Options

Option A: Remote Development (Recommended for daily work)

Work directly on Mac-Studio files from MacBook using VS Code Remote-SSH or JetBrains Gateway.

VS Code Remote-SSH:

  1. Install "Remote - SSH" extension
  2. Press Cmd+Shift+P → "Remote-SSH: Connect to Host"
  3. Select mac-studio
  4. Open folders directly on Mac-Studio

Benefits:

  • Single source of truth
  • No sync conflicts
  • Works over any network via Tailscale

Option B: Rsync Sync (For offline work)

Use the sync script when you need a local copy (travel, unreliable network):

# Before going offline
./sync-ecfx.sh pull --target=all

# After returning online
./sync-ecfx.sh push --target=all

Hybrid Approach (Best of both)

  • Daily work: Remote development via VS Code Remote-SSH
  • Travel/offline: Rsync pull before disconnecting
  • Dotfiles: Always keep synced on both machines

Troubleshooting

Tailscale Not Connected

# Check status
tailscale status

# If "Logged out", authenticate:
# Open Tailscale from menu bar → Log in

MagicDNS Not Resolving

# Check if MagicDNS is enabled
tailscale debug netmap | grep DNS

# Try the Tailscale IP directly
tailscale status  # Get IP (100.x.x.x)
ssh traviscarter@100.x.x.x

SSH Connection Refused

  1. Ensure "Remote Login" is enabled on target machine:

    • System Settings → Sharing → Remote Login → On

  2. Check Tailscale is connected on both machines

  3. Test with Tailscale IP:

    tailscale ip -4 mac-studio  # Get IP
ssh traviscarter@<ip>

Slow Connection

Tailscale uses direct connections when possible, but may relay through DERP servers if direct path fails.

# Check connection path
tailscale ping mac-studio

# Should show "pong from mac-studio via direct"
# If it shows "via DERP", there may be NAT issues

Security Notes

  • Tailscale uses WireGuard encryption
  • Only devices signed into your Tailscale account can connect
  • No ports exposed to public internet
  • Access control can be configured in Tailscale admin console

Useful Commands

# Show connected devices
tailscale status

# Ping another device
tailscale ping <hostname>

# Get Tailscale IP of a device
tailscale ip -4 <hostname>

# Show network information
tailscale netcheck

# Check debug info
tailscale debug

Related Files

  • ~/.ssh/config - SSH configuration with Tailscale hostnames
  • ~/dev-tooling/sync-ecfx.sh - Rsync script for offline sync