First, install the Tailscale App using the Synology Package manager. Don’t try to initialize using the UI since this will only work with the commercial tailscale service, not with headscale.
Then login to the NAS using SSH (I’m using the admin account) and run sudo su to run
You should see the following shell prompt:
ash-4.4#
Now you can initialize tailscale using the tailscale command similar to our previous post How to connect tailscale to headscale server on Linux. In my case, I needed to use the --reset flag in order for the command to work.
tailscale up --reset --login-server https://headscale.mydomain.com --authkey ... --accept-routes
This will login to your server just like the normal (non-synology) tailscale client does.