Remote Development — Work on Another Machine via SSH · Tailscale · VS Code Remote

"Keep the powerful desktop at home and travel light" or "use a GPU workstation remotely" — same scenario. Core tools: Tailscale (zero-config VPN) + SSH + VS Code Remote-SSH + tmux. Set up once and a cafe feels like your desktop.

TL;DR

1. Tailscale — mesh VPN that punches NAT/firewalls. Connect machines without a corporate VPN
2. SSH — all traffic after auth
3. VS Code Remote-SSH — edit remote files locally as if they were local
4. tmux — session persistence. Work survives disconnects
5. Mosh (optional) — SSH alternative stable on mobile networks

Prerequisites

• SSH + accounts + internet on both ends
• (Optional) No need for a domain or static IP — Tailscale handles it

1. Tailscale Setup

Tailscale is a WireGuard-based mesh VPN. Install on each machine + log into the same account → private IPs (100.x.x.x) are assigned. NAT punched, direct connect.

1.1 Install

Mac:

brew install --cask tailscale

Windows:

winget install --id tailscale.tailscale

Linux (Ubuntu):

curl -fsSL https://tailscale.com/install.sh | sh

1.2 Sign In

On each machine:

sudo tailscale up      # Mac/Linux
# Or use the GUI tray → Login

Opens a browser → sign up with Google/GitHub/Microsoft (Tailscale free: 100 devices).

1.3 Find the Machine IP

tailscale ip -4
# 100.x.x.x

Or see all machines at admin.tailscale.com.

1.4 Machine Names (MagicDNS)

Admin console → DNS → enable MagicDNS. Now SSH by name like desktop.tail-scale.ts.net:

ssh me@desktop
# (.tail-scale.ts.net auto-appended)

Once enabled, never think about private IPs again. The rest of this guide assumes the name desktop.

2. SSH Prep

2.1 Enable SSH on the Remote

Mac (remote):

• System Settings → General → Sharing → Remote Login ON

Windows (remote):

• Settings → System → Optional features → install OpenSSH Server
• PowerShell (admin):

  Set-Service -Name sshd -StartupType Automatic
  Start-Service sshd

Linux (remote):

sudo apt install openssh-server
sudo systemctl enable --now ssh

2.2 Register the SSH Key

Add the local public key to the remote's ~/.ssh/authorized_keys:

# Local
ssh-copy-id me@desktop
# Or manually on the remote:
mkdir -p ~/.ssh && chmod 700 ~/.ssh
echo "ssh-ed25519 AAAA..." >> ~/.ssh/authorized_keys
chmod 600 ~/.ssh/authorized_keys

2.3 Connect

ssh me@desktop
# Or directly to 100.x.x.x

3. VS Code Remote-SSH

Edit remote files at local speed from VS Code.

3.1 Install the Extension

VS Code marketplace:

• Remote - SSH (ms-vscode-remote.remote-ssh)

Or:

code --install-extension ms-vscode-remote.remote-ssh

3.2 Connect

VS Code Command Palette (⌘⇧P / Ctrl+Shift+P) → Remote-SSH: Connect to Host → enter me@desktop.

First connect installs VS Code Server on the remote (~50MB, once). Subsequent connects are instant.

3.3 Use

Bottom-left shows SSH: desktop. File → Open Folder → open ~/work/repo on the remote. Extensions install on the remote (e.g., the Python extension uses the remote's Python env).

3.4 Recommended Extensions (remote)

• ESLint / Prettier
• Python / Pylance
• Docker
• (Keep theme/keymap on local for neatness)

4. tmux — Session Persistence

If SSH drops, work stays:

4.1 Install (remote)

# Mac / Linux remote
brew install tmux   # Mac
sudo apt install tmux   # Ubuntu

4.2 Use

ssh me@desktop
tmux new -s work       # start session
# ...work...
# Ctrl+B, D  → detach (session keeps running)
 
# Later
ssh me@desktop
tmux attach -t work    # reattach

4.3 Key Shortcuts

4.4 Auto-attach

.zshrc (remote):

if [[ -z "$TMUX" && -n "$SSH_CONNECTION" ]]; then
  tmux attach -t main || tmux new -s main
fi

SSH in → auto-attach to main (or create).

5. Mosh — On Mobile Networks

If SSH drops a lot during transitions (5G ↔ Wi-Fi), use Mosh (Mobile shell). UDP-based, local echo, auto-recover.

brew install mosh
# Remote
sudo apt install mosh

mosh me@desktop

Uses SSH for auth + UDP ports 60000-61000. No extra firewall configuration if going through Tailscale.

6. Scenario: GPU Workstation Remote

Goal: train ML on desktop GPU from a laptop.

# On the laptop
ssh me@gpu-workstation
tmux new -s train
 
# Inside tmux
cd ~/projects/ml
python train.py --epochs 100
 
# Ctrl+B, D to detach
 
# Close the laptop, move to a cafe
# Reconnect
ssh me@gpu-workstation
tmux attach -t train
# Training continues

Edit with VS Code Remote + run training in tmux. Both run together.

7. Security

Tailscale ACL (optional)

By default, all machines on the same account see each other. For corp/family mix:

• Admin console → ACLs → JSON policy
• Tag-based permissions (tag:dev, tag:home)

Harden SSH

On the remote /etc/ssh/sshd_config:

PasswordAuthentication no       # keys only
PermitRootLogin no
AllowUsers me

sudo systemctl restart sshd

1Password SSH Agent

See password manager. With Tailscale + 1Password agent, SSH needs only biometric — no passphrase.

Verification

1. tailscale status on both → "online"
2. ssh me@desktop → instant login (one passphrase or biometric)
3. VS Code Command Palette → Remote-SSH Connect → edit + save → changes reflect on the remote
4. tmux new -s test → detach → tmux attach -t test → state preserved
5. mosh me@desktop → drop Wi-Fi, switch networks → session auto-recovers

Troubleshooting

Tailscale Doesn't Connect

• Both machines run tailscale up and signed in
• Admin console shows both as "Connected"
• Firewall — Tailscale uses 41641/UDP. Corp networks may block (falls back to DERP relay)

ssh: connect to host 100.x.x.x: Connection refused

• SSH service isn't running on the remote (re-check §2.1)
• Windows: Get-Service sshd is Running?

VS Code Remote Is Slow

• First connect installs Server — slow once
• If going via internet (Tailscale Direct failed) — tailscale ping desktop to see direct vs DERP

Colors Broken in tmux

.tmux.conf:

set -g default-terminal "screen-256color"
set -ga terminal-overrides ",xterm-256color:Tc"

Mosh Won't Connect

UDP 60000-61000 blocked — common on corporate networks. Fall back to SSH. Mosh needs UDP.

SSH Agent Forwarding (be careful)

For SSH-from-remote-to-another-remote, ssh -A. Only when the intermediate remote is trusted — a malicious root would see keys.

References

• Windows initial setup / Mac initial setup — prerequisites
• Windows git auth / password manager — SSH key management
• Tailscale (official)
• VS Code Remote-SSH
• Mosh

Changelog

• 2026-05-12: First draft. Tailscale · SSH · VS Code Remote · tmux · Mosh + scenario · security + six troubleshooting cases.