Logging into Tailscale using Microsoft O365 Credentials on Windows

Follow these steps to log into Tailscale using Microsoft O365 credentials:

  1. Pre-requisites:
    • Ensure the PC is connected to the internet.
    • Confirm that Tailscale is installed.
  2. Locating the Taskbar Icon:
    • Look for the Tailscale icon in the Windows taskbar, usually near the clock.
  3. Clicking the Icon:
    A. Click on the Tailscale icon, or right click and select ‘log in’ to initiate the login process.
    B. If this doesn’t work, check if there is using multiple network interfaces (e.g., Wi-Fi and Ethernet) simultaneously. If multiple interfaces are being used,  set the interface’s “Automatic Metric” to manual and enter a value.
  4. Microsoft O365 Sign-in:
    • A Tailscale login window will appear.
    • Select the “Sign in with Microsoft” option.
  5. Redirect to Microsoft Login:
    • The default browser will be opened and redirected to the Microsoft O365 login page.
    • Use O365 credentials (email and password).
  6. Two-Factor Authentication (if applicable):
    • If prompted for two-factor authentication, complete the required steps.
  7. Granting Permissions (if applicable):
    • If windows, or O365 asks to grant permissions, review the requested permissions and click “Allow” or “Accept.”
  8. Connecting to the Network:
    • After successful login, the Tailscale app will attempt to establish a secure connection to the network.
  9. Check connection
    • Check if it says ‘connected’ or ‘disconnected’ in the taskbar.
  10. Done. 

[Solved] Clicking on Tailscale icon does not let me login

Occasionally i have come accross a Tailscale client that does not initially want to display the log in page.

I originally also tried running CLI commands like “tailscale up –authkey xxxxxxxxxx” as well – it seems to hang.

tailscale login icon in taskbar

So when CLI and clicking on the icon in the taskbar via the GUI to log in doesn’t work – Check your network cards!
This is usually caused when Tailscale cannot tell which network card has priority.

On Windows:

Win + R //to open run
ncpa.cpl //to open the network settings
Select main network card
Open Properties, then IPv4
Click on Advanced, untick ‘Automatic Metric
Set to 10.

setting network card interface metric to solve tailscale issues

Try again. Chances are, tailscale will now let you login and generate the login page popup allowing sign on. Authkey authentication should also now work.

tailscale login screen in browser