tailscale-install

Tailscale Install

Install Tailscale and connect a device to a tailnet. Handles platform detection, installation, verification, and initial authentication.

What this skill does

1. Detects the platform (OS, distro, WSL2, container).
2. Checks for an existing Tailscale installation.
3. Installs Tailscale using the appropriate package manager.
4. Verifies the installation and daemon status.
5. Guides initial connection to the tailnet.

Platform detection

Detect the environment before selecting an install method. Check WSL2 first to avoid installing the Linux package inside a WSL2 instance.

1. Check WSL2 (but not containers running on WSL2)
   ├─ grep -qi microsoft /proc/version 2>/dev/null
   ├─ AND [ ! -f /.dockerenv ] (not a container)
   ├─ WSL2 → go to "WSL2 special case"
   └─ Not WSL2 (or container) → continue

2. Check OS
   ├─ uname -s → Linux → detect distro
   ├─ uname -s → Darwin → macOS
   └─ OS is Windows → PowerShell commands

3. Detect Linux distro
   ├─ . /etc/os-release && echo $ID
   ├─ debian, ubuntu → apt
   ├─ fedora, rhel, centos, amzn → dnf/yum
   ├─ arch, manjaro → pacman
   ├─ alpine → apk
   ├─ opensuse*, sles → zypper
   └─ other → curl one-liner fallback

Existing install check

Before installing, check if Tailscale is already present:

tailscale version 2>/dev/null

If installed:

• Report the current version.
• Check daemon status: sudo systemctl status tailscaled (Linux).
• Check connection: tailscale status.
• Stop here unless the user requests a reinstall or upgrade.

If not installed, proceed to installation.

WSL2 special case

WSL2 shares the Windows host network stack. Installing Tailscale inside WSL2 creates conflicting WireGuard tunnels. Do not install the Linux package in WSL2.

Detection (exclude containers running on WSL2 hosts):

grep -qi microsoft /proc/version 2>/dev/null && [ ! -f /.dockerenv ] && echo "WSL2 detected"