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A few days ago, my friend changed their Gmail password. Using Outlook 2011 , the authentication to that account now fails, and re-entering the new password doesn't satisfy it.  Have zapped the account and re-added it.  Have removed an Keychain entries to this account. 

The problem I think is that Outlook prompts us for password, but it doesn't pass that off to MacOS/Safari for the special Gmail authentication window.

Looking online, I see that this is a common problem. For many, it was fixed by updating Outlook. We've tried in both Outlook 2011 (which he prefers) and Outlook 2016 and neither will authenticate to his Gmail account. (works fine on phone gmail web interface).

Have also "reduced" the Google security to allow for "insecure connections", but that didn't make a difference.

His Mac is running the latest Mojave and I know there were an problem with custom GSuite domains for a while (with Apple Mail), which cleared up with updates from Apple & Microsoft.  But this is a standard Gmail account, and it's Outlook, so I don't think that's involved.

Research is not revealing any further ideas on what to try. Moving to Apple Mail is NOT an option.

2 Answers
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Outlook 2011 definitely requires an “app specific password” because it can’t handle oauth. Resetting the Google password may invalidate existing app specific passwords. 
Outlook 2016/2019/365 should however properly present the “mini web page” Google authentication. Make sure you’re using an up to date app. Possibly also check that there is no firewall, like Little Snitch, blocking the outgoing request on a different port. 

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You are correct Graham. Outlook 2011 requires an app specific password and doesn't recognize Google's new oauth trigger. 

What threw me off the trail was Gmail had been working fine under his Outlook for so many years, I didn't realize that his login had been "grandfathered in".  And once I went looking for app specific passwords, I didn't realize that he had to have Google's 2-factor authentication turned on first, in order to see to link to setup for app specific passwords in his Google account security area.  

Thanks for your help.

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