Outlook 2019 keeps asking the password for Gmail. Why?

Question

Good day!

When I open Outlook 2019 on my laptop to access Gmail accounts, the Gmail window to ask for the password pops up. The 2-factor authentication is enabled, so as the app-password.

If I insert the password, t works while the laptop is on. Once I restart Windows and open Outlook doesn't work anymore.

It is very annoying.

I have already tried all possible steps to re-access Gmail through Outlook 2019.

What can I do to come back to the previous status when the link Outlook 2019 - Gmail worked automatically.

Please note that I can continue accessing Gmail accounts through Outlook 2016 on my desktop computer without any problem.

Many thanks in advance,

Alberto

P.S.: After posing the above question in the MS Community and having a few exchanges providing configuration details, I was diverted to this blog.

Answer 1

Hi @Alberto68

For our better research, please provide more information about this case:

• What does the pop-up asking for the password look like? Can you provide a screenshot (please be careful to cover your personal privacy information.
• Is the web version of Gmail working?
• What is Outlook client version? Please make sure to upgrade to the latest version.

There are many reasons for this issue, try these are a few possible solutions:

1. Check if you have Outlook saved credentials (passwords) stored in Windows Credential Manager. (Control Panel>All Control Panel Items>User Accounts>Manage your credential > Windows Credentials.)
2. Gmail accounts have two-factor authentication enabled, which requires you to enter a verification code or use an app-specific password when signing in from a new device or app. Outlook may not handle this process smoothly and may constantly ask you for your password. To resolve this issue, you can disable two-factor authentication in your Gmail settings or use an app password instead of a regular password when adding your Gmail account to Outlook.
3. Try logging in to Gmail for the web. If everything is fine with Gmail.com, considering that it may be caused by corrupted profile/data files in Outlook client, it is recommended that you try to create a new profile (Control Panel >Mail >Show Profile >Add) and add an account to test to check if there are some differences.

For more detailed steps, please refer to this blog: Outlook Keeps Asking for Gmail Password: 5 Ways to Fix It (windowsreport.com).

Note: Microsoft is providing this information as a convenience to you. The sites are not controlled by Microsoft. Microsoft cannot make any representations regarding the quality, safety, or suitability of any software or information found there. Please make sure that you completely understand the risk before retrieving any suggestions from the above link.

Hope this helps!

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