Debugging TailScale Client on Windows OS
2 min readJun 26, 2021
TL;DR
- Open the Windows CMD and execute the following commands.
cd "C:\Program Files\Tailscale IPN"
tailscale.exe up
tailscale.exe web --listen localhost:8080
tailscale.exe status
After upgrading my laptop to the most recent version of Windows OS, I started experiencing an issue with Tailscale. It was not connecting to the Tailscale service and as such, I could not use it as a VPN.
Here are the errors I encountered:
- Failed to connect to Tailscale Service.
- Error creating Interface.
- Backend error.
Here are the observations I made:
- The Tailscale icon on the System tray/Notification was grey.
- The Tailscale icon when right-clicked showed “Failed to connect to Tailscale Service” instead of “Connected using ……”.
The steps I took to solve the issues are as follow:
- Open the Command Prompt as an administrator.
- Once the Command Prompt is opened, change the directory to Tailscale’s executable directory by entering
cd "C:\Program Files\Tailscale IPN"
and then pressing enter. - Enter
tailscale.exe web — listen localhost:8080
in the command prompt to start a local webserver that binds tolocalhost
and listens for HTTP connection on port8080
. - Using a browser installed on the same computer navigate to
http://localhost:8080/
. - You may be prompted to sign in to your Tailscale account. Sign in and your Tailscale connection should now be working fine.
- To confirm that Tailscale is working properly, enter
tailscale.exe status
on the Command Prompt. This should display information similar to the format below:
xxx.xxx.xxy <YOUR_HOSTNAME> <USERNAME_ON_TAILSCALE.COM> <OS_TYPE> -
xxx.xxx.xyx <YOUR_HOSTNAME> <USERNAME_ON_TAILSCALE.COM> <OS_TYPE> -
xxx.xxx.xyy <YOUR_HOSTNAME> <USERNAME_ON_TAILSCALE.COM> <OS_TYPE> -
- Now that you have connected successfully. I hope this brings a smile to your face.
A few tips on getting the Tailscale Client to work properly:
- Use the Tailscale Command Line Interface as it allows you to debug interactively and efficiently. On Windows, the CLI executable
tailscale.exe
is located in the directoryC:\Program Files\Tailscale IPN\
. - Read the Tailscale logs. On Windows, Tailscale stores its logs in the directory
C:\Windows\System32\config\systemprofile\AppData\Local\Tailscale\Logs
. To make things a little bit easy, look into the most recent log files.