Posts tagged with: howto

I ran into this odd issue when trying to add two Yubico security keys to my Google account on a Windows machine. The process on myaccount.google.com keeps prompting to “Enroll Windows Hello” in order to create passkeys.

If you want to skip the preamble, jump directly to the steps.

Whenever I clicked the “Create a passkey” button in the middle of that page, it opened the special link ms-settings:signinoptions, which opens the Windows OS settings page for sign-in options. My best guess is that Google wants the machine itself to use one of those options, but I prefer not to at this point.

I did some clicking around between the security page, two factor authentication page, and the passkeys page, both with the security key plugged in and without. I don’t remember the exact steps, but I did eventually get to the “Use another device” prompt and was able to set up the passkey on the security key. At that point, I had my first security key and my phone listed as passkeys. I wanted to add my second security key (backups!), but no matter how I tried, I could not get back to that “Use another device” prompt.

I turned to the human internet and found some threads on Reddit. This one in particular had a comment suggesting signing up for Google’s Advanced Protection Program. It is free, so it was possible, but I persisted on mostly in spite because this shouldn’t be so hard!

Fast forward through several more clicking around adventures and here is how I got it to work:

1. Visit https://myaccount.google.com/advanced-protection/onboarding and sign in
2. Scroll down and expand the section “Passkeys and security keys”
3. Select “Create passkey”
4. In the popover, select “Use another device” (screenshot below)
5. Another popover with a QR code instructs to scan with a phone or tablet. Ignore that prompt and click the “Back” button at the lower left of the popover
6. The QR popover will go away and you should see the prompt “Choose where to save your passkey for google.com”. Select “Use an external security key” (screenshot below)
7. From that point, follow the OS prompts to enter a PIN and touch the security key
8. Done! The security key now shows up in the list of passkeys