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Install Tailscale on Windows

Install Tailscale on Windows via winget or the installer. Includes subnet routing, exit node usage, and SSH server setup for remote access.

Shellpowershell
Updated
Script
powershell
# 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.

Why this approach

If your daily-driver machine is Windows and your homelab runs on a Linux cluster, Tailscale is the simplest bridge between them. Install the client on your Windows machine, authenticate, and your Proxmox nodes, NAS, and every Docker service on your LAN become reachable by their Tailscale 100.x.x.x IPs — or by subnet route, the whole 10.x.x.x range — from anywhere, without port forwarding.

The winget install used here is the cleanest option for a command-line setup and for systems managed by automation or documented setup scripts. It installs from the official Microsoft Store source and produces the same full client as a direct download. The direct installer alternative is better for corporate environments where winget isn’t available or for air-gapped machines.

After install, Tailscale runs as a Windows service (tailscaled) that starts with the system — there’s no need to remember to launch it. The tray icon shows connection status at a glance. For Windows machines that don’t have a logged-in user (a server, a headless VM), the service still runs and the CLI tailscale command is available in PowerShell for management.

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
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