Mail keeps asking for a new gmail app specific password

did you deactivate the previous app specific key after assigning a new one? this happens to me occasionally, but not nearly as often as you describe. id say maybe once a year. i recently had to reassign an app specific password for mail and after doing so, i deleted the one that was previously generated, and haven't had an issue since. one thing you might try is to deactivate the gmail account in mail and then set it up as new. i know its not ideal, but its difficult to assign blame to either Apple or Google for this sort of problem and its a lot less hassle than constantly regenerating passwords and having to relearn Googles latest "interface optimization" in order to find the security preferences.

 

I had the same problem with my Gmail and aol accounts under Apple Mail 10.9 and 10.91. Somehow 10.92 fixed it. It's been two weeks or so and not a single request for PW. Before 10.92 it basically happened all day...

 

same problem, I use Thunderbird

 

Alright I searched and found this thread. I'm having the same issue.. any resolution? I see someone talking about 'app specific' passwords... I've looked everywhere and can't find this in my Google Accounts settings. The only thing I see is that my iPhone is allowed access to the account but no settings to create an "app specific password" or anything.

 

I've come across this. Need to remember to update the password in these three places below if using 2-step.

Apple system preferences >> Internet Accounts >> Update password for the gmail account in here with the app specific one you have been given for you mail

Mail >> Preferences >> Select google account >> Outgoing mail server - click drop down menu and select "Edit SMPT Server List" >> update password with the app specific password.

Mail >> Preferences >> Select Google account >> Enter password

did the trick for me.

 

As a side note i often delete references to email passwords from Keychain access manually, then add new password form within Mail Accounts setup. It has a habit of not playing ball.