Google Two Factor Authentication issues

idainc · Aug 28, 2023

I'm using Gmail in outlook desktop version and on my iPhone and have begun getting a nag screen to enter email address, password then acknowledge on my phone. If I use an app specific password on my PC will I also have to set one up to access Gmail on my phone and will it need to be a different one form the PC ? Thanks in advance.

Bastet · Aug 28, 2023

Yes you’ll require an app specific password on any device/mail client which doesn’t use the oauth2 security. Usually it is 1 password per device So different devices will require 2 passwords but you can try using the same password to see if it does work.

idainc · Aug 28, 2023

Thank You. I use a desktop LTSC version of Office 20211 and haven't been successful in getting it to display the password. No problem getting Google to generate the app specific password just cant get it into Outlook.

Bastet · Aug 28, 2023

Office may just require you to set the account up & then authenticate by logging into Google using the pop up which should show.

idainc · Aug 28, 2023

Yes, I was afraid of that. Not an issue but I have to delete the account then reinstall. There is no way to swap out the password like you can with iCloud.

Bastet · Aug 28, 2023

That would be the case. I no longer use Outlook so cannot check.

magpie2025 · Sep 23, 2025

Thanks for raising this—it’s a good example of how 2FA can complicate access across devices. Google’s approach, while occasionally annoying, at least provides a workaround: app-specific passwords. These let you bypass the 2FA prompt in apps that don’t support modern authentication, and you can generate separate ones for each device or app if needed.

Unfortunately, Microsoft doesn’t offer anything comparable when SMS-based 2FA fails. In my case, I was locked out of my account entirely because their SMS servers weren’t delivering codes. No backup method, no recovery key, no working support. Just a dead end. And when your Microsoft account is tied to your OS, email, and cloud services, that’s not just inconvenient—it’s catastrophic.

So while Google’s system isn’t perfect, it’s at least survivable. Microsoft’s, when broken, is unforgiving. Security should never come at the cost of basic access.

antspants · Sep 23, 2025

magpie2025 said:
Thanks for raising this—it’s a good example of how 2FA can complicate access across devices. Google’s approach, while occasionally annoying, at least provides a workaround: app-specific passwords. These let you bypass the 2FA prompt in apps that don’t support modern authentication, and you can generate separate ones for each device or app if needed.

Unfortunately, Microsoft doesn’t offer anything comparable when SMS-based 2FA fails. In my case, I was locked out of my account entirely because their SMS servers weren’t delivering codes. No backup method, no recovery key, no working support. Just a dead end. And when your Microsoft account is tied to your OS, email, and cloud services, that’s not just inconvenient—it’s catastrophic.

So while Google’s system isn’t perfect, it’s at least survivable. Microsoft’s, when broken, is unforgiving. Security should never come at the cost of basic access.

Are you going to hunt around this forum for bumping 12 month (or older) threads that you can vent in? It’s a bit tedious, especially that you’ve already created your own thread about your frustrations.

magpie2025 · Sep 25, 2025

@antspants, I'm not venting frustrations — I'm sharing a specific, documented experience that could affect any legitimate user. My intention is to bring clarity and help others who may face the same situation. I'm not attacking anyone or any product; I'm pointing out how a recovery system can become inaccessible to the very person it's meant to protect.

If the system worked as expected, there would be no need for this kind of post.

Google Two Factor Authentication issues

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