Debugging TailScale Client on Windows OS

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:8080in the command prompt to start a local webserver that binds to localhost and listens for HTTP connection on port 8080.
• 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 directory C:\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.