Setting up remote development with tailscale and ssh

September 06, 2025

This fall, I have a class called operating sytems that requires me to dual boot ubuntu w/ my mac. I already have a thinkpad that has ubuntu installed but I decided I could just ssh into the computer from my mac. I think this was a good way for me to understand ssh a little better.

This guide documents the exact steps to set up a Mac (client) to SSH into a ThinkPad running Ubuntu (server) securely and reliably, even across different networks. It also covers keeping the Ubuntu laptop running with the lid closed and ensuring services survive reboots.

1. Install SSH on Ubuntu

sudo apt update
sudo apt install openssh-server -y
sudo systemctl enable ssh
sudo systemctl start ssh

SSH server will now auto-start on every boot.

2. Install Tailscale for Remote Access

Tailscale creates a private VPN mesh so both laptops can connect as if they’re on the same LAN.

On Ubuntu:

curl -fsSL https://tailscale.com/install.sh | sh
sudo systemctl enable tailscaled
sudo systemctl start tailscaled
sudo tailscale up

On macOS:

Download from https://tailscale.com/download and install.
Sign in with the same account.

Verify connectivity:

tailscale ip

Note the 100.x.y.z IP.

Test SSH:

ssh ubuntu-username@100.x.y.z

3. Configure SSH Alias on macOS

Create/edit ~/.ssh/config:

mkdir -p ~/.ssh
nano ~/.ssh/config

Add:

Host thinkpad
    HostName 100.x.y.z
    User ubuntu-username

Now connect simply with:

ssh thinkpad

4. VS Code Remote SSH Setup

Install VS Code on macOS.
Install extension: Remote - SSH.
Cmd+Shift+P → Remote-SSH: Connect to Host → select thinkpad.
VS Code will auto-deploy its server to the ThinkPad.

5. Prevent Sleep When Lid is Closed

By default Ubuntu suspends on lid close. Disable this behavior:

sudo nano /etc/systemd/logind.conf

Set/uncomment:

HandleLidSwitch=ignore
HandleLidSwitchDocked=ignore

Restart (safer than reloading logind directly):

sudo reboot

The laptop will now keep running with the lid closed.

⚠️ Note: With lid closed, cooling is reduced. Heavy loads may cause overheating.

6. Ensure Auto-Restart of Services After Reboot

Both SSH and Tailscale are enabled via systemctl. After reboot, they start automatically.

Test:

sudo reboot

Wait 1–2 minutes, then SSH from macOS:

ssh thinkpad

7. Handling Power Loss / Shutdown

If the ThinkPad is fully powered off, you can’t reach it until it boots. Options:

BIOS/UEFI → Enable Power on AC attach (auto-boot when power is restored).
Wake on LAN (WoL) → Only reliable on Ethernet, rarely works on Wi-Fi. Allows remote power-on with a magic packet.

Summary

SSH + Tailscale makes remote dev possible across any network.
Lid close won’t suspend the Ubuntu server.
SSH and Tailscale auto-start after reboot.
Full shutdown still requires physical power-on unless BIOS/WoL is configured.

This setup makes the ThinkPad behave like a headless server, accessible from VS Code or plain SSH anywhere.

That’s about it. I used ‘thinkpad’ since it was the one that I used but you can go ahead and name your server whatever you want.