Install Tailscale on Windows

# Install via winget (Windows Package Manager — built into Windows 10 1709+)
winget install --id Tailscale.Tailscale --source winget --accept-package-agreements --accept-source-agreements

# Start Tailscale (it also auto-starts on login after install)
Start-Process "C:\Program Files\Tailscale\tailscale-ipn.exe"

# Bring up Tailscale and authenticate
tailscale up

What this does

Installs Tailscale on Windows using winget (Windows Package Manager). After install, Tailscale runs as a system service and a tray icon app, and starts automatically on login.

Prerequisites

• Windows 10 1709 or later / Windows 11
• winget available (comes with App Installer — update via Microsoft Store if missing)
• A Tailscale account

Alternative: direct installer

Download the MSI installer directly from tailscale.com/download/windows if you prefer not to use winget.

Using the CLI

After install, tailscale.exe is on your PATH:

tailscale status           # show connected nodes
tailscale ip -4            # your Tailscale IP
tailscale ping hostname    # test connectivity
tailscale up --accept-routes  # accept subnet routes from other nodes

Enable Windows SSH server for remote access over Tailscale

# Install OpenSSH Server (run as Administrator)
Add-WindowsCapability -Online -Name OpenSSH.Server~~~~0.0.1.0

# Start the service and set to auto-start
Start-Service sshd
Set-Service -Name sshd -StartupType Automatic

# Verify the firewall rule exists (Tailscale traffic bypasses Windows Firewall by default)
Get-NetFirewallRule -Name "OpenSSH-Server-In-TCP"

Then SSH into the machine: ssh user@100.x.x.x (use the Tailscale IP from tailscale ip -4).

Notes

• Tailscale installs two components: a background service (tailscaled) and a tray app (tailscale-ipn.exe)
• The Windows Firewall is automatically configured during install
• For headless/server Windows installs, use tailscale up from an elevated PowerShell session
• Key expiry can be disabled per-device in the admin console