Outlook 2016 repeatedly asking for Password for gmail account

Karl, many thanks yet again for the lightning-quick response. I'll type my answers in Bold font to distinguish them easier.

Karl, are you aware of any way of stopping this crazy situation other than never turning off any device so that one never has to log in ever again? e.g. what would happen if I were to turn off two-step verification now that Outlook is working with the App Password?

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.

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.

Thanks again in advance, John

BTW: can you please advise as to where you redirected my post about OneDrive . . . I can't find it, nor your response.

Karl, are you aware of any way of stopping this crazy situation other than never turning off any device so that one never has to log in ever again? e.g. what would happen if I were to turn off two-step verification now that Outlook is working with the App Password?

Short answer: If you turn off 2FA, it will stop working

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? If yes, do you by any chance have your browser set to clear cookies every time the browser is closed?

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). 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

Before getting onto my reason for this post, please forgive me for venturing my heartfelt/honest opinion, but if I were PhilC8, I would bite the nuclear bullet and do a CLEAN install of Windows and then install Office 2019 with a "virgin" Outlook . . . fiddling around in settings, which even for the technical experts are not always easy instructions to follow, will possibly only lead to more weeks of frustration . . . instead of maybe a max of 24 hours to set up all of your various programs and settings.

Am not adverse to the nuclear option when called for but not my first choice in dealing with an issue. It's a really radical, painful and needless time-consuming way to go it the reason was simply because a box was checked to prevent the download of images - just sayin. Also, what many people don't realize is that creating a new Outlook profile is effectively starting over for all intents and purposes if an issue is relates to an email account or something not specifically related to a programmatic problem which doesn't remotely sound like the cause for images not downloading hut even it were, repairing (reinstalling) Office should solve that if a corrupt program file is the cause.

BTW PhilC8: I am also of the veteran set . . . well . . . mid 70's at least. I have no IT or AI background and am self-taught by trial and error. However, with a little patience and because I have been married forever, am able to follow instructions Ha ha!!!!

FWIW - sounds like we are all kindred spirits in terms "veteran set" - my IT days started back in 1970 😊

Hi again Karl, Yes it's me, John, who started this thread.

PhilC8, no problem that you "hijacked" it (as you called it) . . . you needed help and Karl was really fantastic for my problem.

Before getting onto my reason for this post, please forgive me for venturing my heartfelt/honest opinion, but if I were PhilC8, I would bite the nuclear bullet and do a CLEAN install of Windows and then install Office 2019 with a "virgin" Outlook . . . fiddling around in settings, which even for the technical experts are not always easy instructions to follow, will possibly only lead to more weeks of frustration . . . instead of maybe a max of 24 hours to set up all of your various programs and settings.

BTW PhilC8: I am also of the veteran set . . . well . . . mid 70's at least. I have no IT or AI background and am self-taught by trial and error. However, with a little patience and because I have been married forever, am able to follow instructions Ha ha!!!!

OK, back to Two-Step Verification:

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) . . . . . .

Karl, are you aware of any way of stopping this crazy situation other than never turning off any device so that one never has to log in ever again? e.g. what would happen if I were to turn off two-step verification now that Outlook is working with the App Password?

I appreciate that this is a Google Issue but, to me at least, it just seems like two small boys fighting over a ball in the playground, "It's mine and you can't share it" or who has the biggest whatever . . . the only difference is that these two small boys are multi-billionaires fighting over who has the most secure apps, and you can't share mine and anyway, "mine's bigger than yours".

Best regards to you both.

With fingers crossed, "highjacked" John

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!!!

OK - let's get the simple stuff out of the way so we can focus on the important stuff

#1 - <Email Account> versus <Outlook Profile>

From your description, you configured the Gmail account in the existing profile assuming that you first deleted the GMail POP account. which would have been required in order to add the Gmail account again to the same Outlook profile. As a FYI, you can't have the same account configured at the same time using 2 different profiles (i.e. POP & IMAP)

Another point to be aware of, when you remove a POP account from an Outlook profile, it does not remove the PST file that was associated with. That;s significant for 2 reasons

a) the Outlook Navigation Pane (the left panel in Outlook, otherwise called the <Folder List>) is a list of data files configured in Outlook. You can see what those files are by going to

<File> --> <Account Settings> --> <Data Files> tab

*** the data file with the checkmark beside it is the <default data file> for the Outlook profile (there can only be on default data file). This is where the default contact / calendar folders are stored and going by everything - the PST file is set as the <default data file>. If it's not - let me know otherwise everything is exactly as expected to this point.

b) you mentioned that when you added the account again using IMAP, a new set of folders were created. That is normal behavior. Every IMAP account has its own OST data file or to put it another way, with its own set as folders

Also as a FYI, just in case you are not aware of this, the OST file for an IMAP account is a mirror of what is contained on the server and you can control how much data is kept locally by adjusting the <oflline slider>. That's done by

<File> --> <Account Settings> --> <Email> tab --> select the IMAP account and adjust accordingly as shown in the screenshot

#2 - Missing images

a) does this apply to any and all messages you receive that contain images or just from specific senders?

b) to go through the basics regarding this (you may have already answered this and I missed it so apologize if that's the case

From within Outlook, when you go to

<File> --> <Options> --> <Trust Center> --> click on <Trust Center Settings>

Are the boxes for not downloading images checked or unchecked as shown in this screenshot? If checked, that would result in what you are describing

If these options are "unchecked" and the issue applies to all messages with images - then will go the new Outlook profile route but will deal with that if necessary in a separate post to keep things simple - will let you digest all of this first and ask any questions about it if you have any