Outlook 2016 repeatedly asking for Password for gmail account

Short answer: If you turn off 2FA, it will stop working. Sorry, but could you please clarify the "it"? Do you mean that Outlook will stop working with gmail again or that 2FA will stop and I won't need it anymore? I'm afraid you mean the former, but even at our ages, we can still dream.

"It" means Outlook won't be able to connect to the account and will keep asking for a password

As feared, it is a right royal pain in the proverbial. As Karl advised, with an App Password, it got Outlook syncing emails with gmail. However, now, every time I want to sign into and/or otherwise open Google or gmail, which is multitudinous times a day, they are requesting authorisation, despite ticking the box about "not asking again on this device" every time (or words to that effect) . . . . . .

Am I correct in assuming that by "sign into and/or otherwise open Google or gmail" - you are referring to "browser" based activity? Yes! it might sound crazy to some, but I use gmail in a Google Chrome browser to quickly read emails and file them, but draft and respond in Outlook, which is far more user-friendly for drafting etc.. If yes, do you by any chance have your browser set to clear cookies every time the browser is closed? No, most definitely not.

P.S. Forgot to mention another quirk: I also set up my wife's gmail and our company gmail on Outlook and, would you believe, the former worked straight away but the latter required setting up Two-Step Verification and an App Password!!!

How was the account configured? (POP or IMAP). All my/our accounts are configured IMAP. POP accounts will always require 2FA and an <App Password>. If both are configured as IMAP will have to ask my counterpart who is far more familiar with corp Google accounts then I am which I'll do as soon as you let me know. May have misled you by referring to "our company gmail". It's a small private consulting company, just my wife and I, and it's an ordinary/normal gmail account.

Questions:

#1 - Does this involve one computer or two computers in terms of the behavior?

#2 - Does the need to constantly sign-in apply to both email accounts? On both computers (if two are being used?

#3 - If two computers, are both versions of Outlook '2016 at the same version / build level? If everything is equal for both accounts using the same version of Outlook '2016, don't know why one would behave differently. IMAP accounts shouldn't require 2FA if everything is up-to-date

Karl,

Thank you again for your very detailed walk through notes I have worked through a lot of it and I am drafting a reply, which was why I wanted to post some screen capture bits (edited for security).

, but I must wait my place :).

No need to "wait your place"........... I may be old but can still answer both 😊

As for adding some screen shots - just in case this is of any use (wasn't clear as to whether that was a question or just a statement so apologize if this is info you don't need

How to include a screenshot in your post - Microsoft Community

Dear John,

I am thankful for your kind reply and acceptance that I truthfully didn't mean to 'hijack' your post. I did laugh at your reply regarding 'married and know how to follow instructions' :) though my dear lady wife who have been with me over 46 yrs may well suggest otherwise ;)

I was looking at how to reply to Karls questions and hit a similar problem to you, that I cannot upload screen images. I don't use One Drive, Dropbox or any of those online systems having an innate fear of using them, forgetting passwords and putting stuff that should be confidential into places where it may get forgotten, lost or hacked. Did I say that computers and these new systems have started to leave me paranoid. It is the reason I wanted to continue using Outlook and keep my mails on my systems ( I used to wipe everything off gmail once it was downloaded safe... until the 2 factor thing hit).

Karl,

Thank you again for your very detailed walk through notes I have worked through a lot of it and I am drafting a reply, which was why I wanted to post some screen capture bits (edited for security). I will step back a moment in this thread, as it is John's post, and I don't want to invade his getting your extremely kind and valuable help regarding his login setup.

If I may I will post my answers to the points of your last reply to me here later as I have walked through all the directions you gave and have answers, but I must wait my place :).

Thank you both

Phil

Stop press: . . . immediately after sending the previous post, I found the one about OneDrive.