YubiKey Failing Re-Validation of Microsoft 365 Account on Both Ventura 13.2 and iOS 16.3

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Level 1

4 points

YubiKey Failing Re-Validation of Microsoft 365 Account on Both Ventura 13.2 and iOS 16.3

I successfully set up YubiKeys with Microsoft 365 on both an M1 MacBook Pro and an iPhone 13 Pro, running Ventura 13.2 and iOS 16.3 respectively.

The setup worked fine in both cases.

After a few days, I got a prompt to re-enter my Exchange password, on both devices.

On both devices, after I enter my password in the Microsoft box, the next screen asks me for the MFA method. If I choose Security Key, I never get the next window I saw during the initial setup that asks me to use the key. Both systems just hung.

After backing out and being prompted again to re-enter my password, I choose to use the "text me a code" method, which worked just fine.

Suspecting an Apple bug, so asking here if anyone else has seem similar?

Thanks,

Mark

iPhone 13 Pro Max, iOS 16

Posted on Jan 27, 2023 9:52 AM

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Answer 1

Jan 29, 2023 3:53 PM in response to Customer510

Hi Customer510,

Thanks for coming to Apple Support Communities for help today.

It sounds like this issue is resolved with the text method. However, since this does involve third-party software and security, we'd advise contacting your Exchange Administrator and Yubico for further help.

Have a fantastic day!

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Answer 2

Customer510 Author

Level 1

4 points

Jan 30, 2023 5:28 AM in response to MichaelB2019

Thanks for the reply. We have also opened up a Support Case with Microsoft on this.

At this writing to be clear, I wouldn't consider this "resolved". The goal in using YubiKeys is to get away from using any SMS validation, which method is subject to SIM-swap, MITM and social engineering attacks. Use of any supported FIDO2 hardware keys eliminates those risks. We just happened to choose YubiKey.

Also, because the second response window that never appears is painted by Mac/i-OS, there is a possibility that Microsoft's end is successfully asking to paint the window, but that there is a bug in Mac/i-OS which prevents the re-validation window (but not the original second window from the initial key setup) from appearing -- which is why I posted here.

In any event, I'll update this thread when we hear back from Microsoft.

Thanks again for the reply,

Mark

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YubiKey Failing Re-Validation of Microsoft 365 Account on Both Ventura 13.2 and iOS 16.3

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