Outlook 2019 keeps asking the password for Gmail. Why? - Microsoft Q&A (2024)

Hi SokiGuo-MSFT,

Thank you for your reply.

Please find enclosed some screenshots and I try to address your questions:

  1. Already clean passwords stored in “Windows Credential Manager”.
  2. If I turn off the two-factor authentication on Gmail side, this will jeopardise the access on my desktop computer, where Outlook 2016 continues to work fine.
  3. Already tried this path, but the issue remain unchanged.

A couple of additional clarifications.

The two-factor authentication is on since mid-2021, enabling the app -password, and this has always worked well for my desktop computer and for my laptop.
What is strange is that using Outlook 2016 with Win 10 Pro (10.0.19045 Build 19045) on a desktop computer to read/write mails of my Gmail accounts, this continues to work perfectly fine.
The problem appeared 3-4 days ago – most likely after a system update – only on my laptop where I use Outlook 2019 with Win 11 Pro (10.0.22621 Build 22621).

When I start Outlook 2019 on the laptop, the Google window asking for the Gmail password appear twice (I suppose for incoming and outcoming traffic). If I insert the app-password, it tells the password is wrong; if I then insert the password, it goes through two annoying authentication steps with the smartphone.
On the other hand, if I check the access to the Gmail mailbox through the “Mail (Microsoft Outlook)” of “Control Panel”, where I originally inserted the app-password, the test on the account works perfectly fine.

Sorry for the screenshots in Italian, but the sense should be straightforward.
Many thanks,

pop-up-gmail.jpg ; imap-pro.jpg

Outlook 2019 keeps asking the password for Gmail. Why? - Microsoft Q&A (2024)

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