Tailscale

Introduction

Tailscale is a VPN service that uses WireGuard to create a fast, secure, and simple peer-to-peer network. Tailscale is a zero config VPN that works on any platform, service, or runtime. It encrypts all connections using WireGuard and integrates with 100+ tools for easy deployment and management.

Tailscale is a modern VPN built on top of Wireguard. It works like an overlay network between the computers of your networks - using NAT traversal.

Everything in Tailscale is Open Source, except the GUI clients for proprietary OS (Windows and macOS/iOS), and the control server.

The control server works as an exchange point of Wireguard public keys for the nodes in the Tailscale network. It assigns the IP addresses of the clients, creates the boundaries between each user, enables sharing machines between users, and exposes the advertised routes of your nodes.

A Tailscale network (tailnet) is private network which Tailscale assigns to a user in terms of private users or an organisation.

Self Hosting

You can self host a Tailscale server with Headscale + Headscale UI.

Headscale is an open source, self-hosted implementation of the Tailscale control server. Headscale's goal is to provide self-hosters and hobbyists with an open-source server they can use for their projects and labs. It implements a narrow scope, a single Tailnet, suitable for a personal use, or a small open-source organisation.

Headscale Admin is a web frontend for the headscale Tailscale-compatible coordination server.

YouTube - Jim's Garage - Self Host Tailscale with Headscale

Configure and run Headscale

Docker

You can self host a Tailscale server with Headscale + Headscale Admin + Traefik docker containers.

Follow the instructions on the respective web sites and the YouTube (outdated though!) video to get started, including grabbing copies of the docker compose and headscale config/config.yaml files, then edit the first 3 options as follows ...

server_url: https://headscale.mydomain.com
listen_addr: 0.0.0.0:8080
metrics_listen_addr: 0.0.0.0:9090

Running headscale in a container

This is the directory layout for a Docker Compose method ...

/root/docker/stacks/headscale
|-- config
|   `-- config.yaml
|-- data
|   |-- db.sqlite
|   `-- noise_private.key
|-- docker-compose.yaml
`-- run
    `-- headscale.sock

3 directories, 5 files

... and this is the docker compose YAML file which has both Headscale and Headscale Admin containers ...

services:

  headscale:
    container_name: headscale
    volumes:
        - ./config:/etc/headscale/
        - ./data:/var/lib/headscale/
        - ./run:/var/run/headscale/
    ports:
        - 8080:8080
        - 9090:9090
    image: headscale/headscale:0.23.0-alpha12
    environment:
      - TZ=Europe/London
    command: serve
    restart: unless-stopped
    networks:
      traefik:
        ipv4_address: 172.19.0.28
    labels:
      - "traefik.enable=true"
      - "traefik.docker.network=traefik"
      - "traefik.http.routers.headscale.rule=Host(`headscale.mydomain.com`) && PathPrefix(`/`)"
      - "traefik.http.routers.headscale.entrypoints=websecure"
      - "traefik.http.routers.headscale.service=headscale"
      - "traefik.http.services.headscale.loadbalancer.server.port=8080"
      - "traefik.http.services.headscale.loadbalancer.server.scheme=http"

  headscale-admin:
    image: goodieshq/headscale-admin:latest
    container_name: headscale-admin
    restart: unless-stopped
    environment:
      - TZ=Europe/London
    volumes:
        - ./config:/etc/headscale/
        - ./data:/var/lib/headscale/
        - ./run:/var/run/headscale/
    ports:
      - 9999:80
    networks:
      traefik:
        ipv4_address: 172.19.0.29
    labels:
      - "traefik.enable=true"
      - "traefik.docker.network=traefik"
      - "traefik.http.routers.headscale-admin.rule=Host(`headscale.mydomain.com`) && PathPrefix(`/admin`)"
      - "traefik.http.routers.headscale-admin.entrypoints=websecure"
      - "traefik.http.routers.headscale-admin.service=headscale-admin"
      - "traefik.http.routers.headscale-admin.middlewares=auth"
      - "traefik.http.services.headscale-admin.loadbalancer.server.port=80"
      - "traefik.http.services.headscale-admin.loadbalancer.server.scheme=http"
      - "traefik.http.middlewares.auth.basicauth.users=funkyusername:xxxxxxxxxxxxxxxxhashedxxxxpasswordxxxxxxxxxxxxxxx"

networks:
  traefik:
    external: true

Start up the containers, and you should see these lines in the docker logs ...

headscale        | 2024-05-31T10:53:13+01:00 INF Opening database database=sqlite3 path=/var/lib/headscale/db.sqlite
headscale        | 2024-05-31T10:53:13+01:00 INF Setting up a DERPMap update worker frequency=86400000
headscale        | 2024-05-31T10:53:13+01:00 INF listening and serving HTTP on: 0.0.0.0:8080
headscale-admin  | {"level":"info","ts":1717149193.3994539,"logger":"http","msg":"enabling HTTP/3 listener","addr":":443"}
headscale-admin  | {"level":"info","ts":1717149193.4059176,"msg":"serving initial configuration"}

Test the headscale server with curl and the docker image ...

curl 0.0.0.0:9090/metrics
docker exec headscale headscale --help
docker exec headscale headscale version
docker exec headscale headscale nodes list
docker exec headscale headscale apikeys list

Navigate to the Headscale UI web address you provided in the config.yml file with /web at the end - https://headscale.mydomain.com/web) and then you will see an error about Authentication and missing API key.

Generate your server's API key. You only get one chance to see this ...

docker exec headscale headscale apikeys create

... copy it, then go the Headscale UI Settings page and paste it there with your 'server_url' from the config file.

There is NO save settings button, it does it automatically but you can then press the Test Server Settings button.

Yay - you have successfuly set up your own self-hosted Tailscale server! :-)

Now you can add your first client device.

Client Devices

Software Installation

Native

curl -fsSL https://tailscale.com/install.sh | sh

WEB

There is a built-in web interface with tailscale, which you can access by running this command ...

sudo tailscale set --webclient

... and then pointing your web browser at the address it tells you to - e.g. http://100.64.0.1:5252

To stop the web interface, run this command ...

sudo tailscale set --webclient=false

GUI

https://github.com/DeedleFake/trayscale

Docker

https://hub.docker.com/r/tailscale/tailscale

Users

Generate a User on the Headscale server first, then register a Node linked to that User.

docker exec headscale headscale users create <USER_NAME>

Nodes

Registration

Method 1: Register a machine using normal login

On a client machine, run the tailscale login command, which will output a machine key (mkey) ...

sudo tailscale up --login-server <YOUR_HEADSCALE_URL>

On the server, run the headscale nodes command to register that client machine node using that mkey to a User ...

docker exec headscale headscale nodes register --key <mkey:YOUR_MACHINE_KEY> --user <USER_NAME>

Method 2: Register a machine using a pre authenticated key

Generate a key linked to a User ...

docker exec headscale headscale preauthkeys create --reusable --expiration 24h --user <USER_NAME>

This will return a pre-authenticated key that can be used to connect a node to headscale during the tailscale login command on the client ...

sudo tailscale up --login-server <YOUR_HEADSCALE_URL> --authkey <YOUR_AUTH_KEY>

Testing

On the server, run the command to list the connected nodes ...

docker exec headscale headscale nodes list

ID | Hostname      | Name          | MachineKey | NodeKey | User   | IP addresses                  | Ephemeral | Last seen           | Expiration          | Connected | Expired
1  | paully-laptop | paully-laptop | [v6BuV]    | [E5A+n] | paully | 100.64.0.1, fd7a:115c:a1e0::1 | false     | 2024-05-31 12:56:23 | 0001-01-01 00:00:00 | online    | no

Authentication

https://github.com/gmiles32/headscale-authelia

Remote Access

Remote Access using Tailscale

• RustDesk > Settings > Security > Direct IP Access + IP Whitelisting (e.g. tailscale IP range = 100.64.0.x)
• RustDesk > Settings > Security > Password > Use Permanent Password