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Tailscale User Guide

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Joey Holliday edited this page Mar 17, 2021 · 7 revisions

Usually, you can only connect to computers, such as laptops and Raspberry Pi's, that are on the same network as your computer. Even if you are on the same network, you need to know the device's IP address, which might change each day or at different physical locations. A Virtual Private Network (VPN) solves these problems by allowing computers to communicate directly with IP address that do not change no matter how they are connected to the Internet. The team uses a VPN to allow us to just plug-in our computers and devices anywhere and have them talk to each other as if them where all on the same network.

Where to Install Tailscale

Most users should install Tailscale inside their Linux VM, not their host operating system However, if you also want to be able to connect to VPN devices from the Host OS, you should install it there. Be aware that installing it in the Host OS will prevent direct connections to your VM and you may need to add the DNS server 100.100.100.100 to resolve Magic DNS names.

Installation

1. Set your computer/VM hostname

Your hostname will become your computer/VM's unique identifier on the VPN. Personal computers and VM hostnames should contain your name. The team likes to name servers after planets and Raspberry Pi's after moons. Linux hostnames should be all lowercase, short, and easily typeable. Windows hostnames should be all uppercase. MacOS hostnames are by default YourName-TypeOfDevice and do not need to be changed.

2. Install Tailscale

  • Download Tailscale
  • On Linux, skip sudo tailscale up for now and you do not need to use the Admin Console.
  • Skip the directions to login on Windows or MacOS.

3. Ask the team's VPN administrator for a unique authentication key

4. Connect to the VPN with your authentication key

Run the following command, replacing <auth-key> with your key.

  • Linux: sudo tailscale up --authkey <auth-key>
  • Windows: "c:\Program Files (x86)\Tailscale IPN\tailscale.exe" up --authkey <auth-key>
  • MacOS: /Applications/Tailscale.app/Contents/MacOS/Tailscale up --authkey <auth-key>

Usage

After installing Tailscale, you should immediately be able to communicate with other devices on the VPN. Each device is automatically assigned a unique virtual IP address of the form 100.x.y.z. This address will always remain the same. You can find your virtual IP address by following this guide. You can communicate with other computers on the VPN by using their unique virtual IP address. You can also use a feature called Magic DNS that will automatically resolve computer hostnames to virtual IP address. If Magic DNS is working, you should be able to just use the hostname of the device you want to connect to anywhere that you would normally use an IP address.

Tailscale will automatically configure itself to startup automatically, and it does not need to be manually started or configured after initial installation. If you decide to uninstall Tailscale, you can use this guide.

Troubleshooting

  1. Unable to connect to any other devices

Make sure that you didn't sign-in to Tailscale using your own email address. In order to be on the same network as the team you need to authenticate using a one-time authentication key. To verify that it is working you can do tailscale status to view a list of other devices on the network or use tailscale ping <host_name> to check connectivity to a specific host.

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