Outlook 2010 will not connect to Gmail

When I try to open Outlook 2010, instead of automatically logging onto Gmail using my stored password, a box requesting the password is displayed. But when I enter the password for Gmail, clicking on OK, cancel, or exit (red X) simply results in the box instantly reappearing. The problem is with Outlook, not Gmail, as I never am able to get past that password request box. It only disappears when I exit from Outlook.

Sure, I can use Gmail via a browser, but Outlook is integrated with other Office functions and is easier to access while performing other Office tasks.

I tried using System Restore, but the most recent restore file has gotten corrupted. I also have rebooted multiple times and have run Avast Cleanup Premium and antivirus.

Thanks for your suggestion.

I finally navigated to a Gmail announcement that it will no longer connect through less secured clients (such as Outlook 2010) without using two-step authentication and a Gmail-generated one-time password. I went through the process of setting those up and am now back in business. I think so, anyway. Somewhere along the way yesterday I attempted to reinstall Outlook (failed) and ran into difficulty today opening Outlook despite restoring Windows 7 to a point before I started that reinstall. I finally got it up and running again somehow; I'm not even sure how.

You'd think that, instead of just repeatedly refusing to recognize a password, Gmail would generate a message that it is requiring two-step authentication. But no, they make you hunt for the solution. We can chalk that up to competition, I suppose.

Here's the page with the Google announcement:
Less secure apps & your Google Account - Google Account Help

And the page with information about the Google-generated application-specific password:
Sign in - Google Accounts

- - - Updated - - -

Further response: I have to concede that Google did make an effort to alert users that Outlook 2010 would require enhanced security to connect to Gmail. I ran into a couple of emails dated 3/4/22 and 4/29/22 describing the upcoming requirement. However, since it didn't take effect until 6/1/22, I believe they should have run some "time's running out" alerts closer to that date. It would have saved me a lot of time and anxiety.

This isn't enhanced security anything. It's all in an effort to grab more personal information. Especially since I don't think you can use any other 2FA mechanism beyond text, voice or Google Authenticator. Also, 2FA rats you out as well. There are alternatives like Aegis, but it's not coded for Windows and I asked for it to be coded for Windows and was told it will never be. I need 2FA on a multi platform basis. I'm not grabbing the damn phone every time I'm on my computer. So, right now I'm stuck with Authy.

Yeah, that is the correct solution. They indeed made it a pain in the ass to figure out if you ask me. I'm trying to part ways from all Google, but right now my website uses it and another project I have going.

--- It's all in an effort to grab more personal information.

Cannot agree more.
Don't want password assigned by google. but If NOT take it, I need to give up all mails in my app. what a pain.

If my account password assigned by other party, not by myself. for whatever reason I don't like it.

I am moving to a new email app, try to NOT use Outlook any more for the sake.

FFS, man. You're using a 19 year old program. Just install Thunderbird and be done with it.

If you have issues you did something wrong. Outlook ’07 and Gmail: am I SOL?