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

Hi again and good morning to you both. My comments/answers in bold:

PhilC8:

As I said, and really meant, "hijacking" is not a problem!!!

Whilst I understand your reluctance/reticence to go the nuclear route, possibly the main reason I would do it is that I assume your PC is old (you were using Outlook 2010). Maybe not as old as we three, but Old in technology terms. We too still have two old PCs (13 and 10 years) which have been our main workhorses and have been with us on 3 continents. 2 of the newer acquisitions have SSDs and fly by comparison . . . so, rather than send the workhorses to the knacker's yard, decided to install SSD's and relegate the HDDs to data storage. Had to do a bit of reading before "just doing it" . . . but was worth every minute and every penny. Took longer to clean out the dust than install the SSD and Win 10. I couldn't believe the absolutely incredible improvement to the 1st PC . . . so decided to do the 2nd and immediately ordered another SSD. By now, clean installation of Win 10 was becoming a doddle. So, flushed with success, I also decided to resurrect an old laptop and another old PC and donate them. Did not put in SSDs and obviously, didn't reinstall MS Office, as the new users can use the cloud versions. However, they also started working much faster than I remembered because the other advantage of a Clean Install is that you clear out all the junk, old apps and programs . . . most of which you have even forgotten you have or have picked up without even realising.

Karl,

Your Questions:

#1 - Does this involve one computer or two computers in terms of the behavior? Actually four (2 PCs and 2 Laptops). As far as I can tell, it seems to be happening equally on all of them (given that my wife is now complaining about something else, rather than me!!!!)

#2 - Does the need to constantly sign-in apply to both all three email accounts? On both four computers (if two four are being used?) Yes! For some reason it's not respecting the "Don't ask again on this device".

#3 - If two computers, are both versions of Outlook '2016 at the same version / build level? Yes! . . . again, as far as I can tell. No reason to think otherwise. If everything is equal for both all three 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. The 3 Google/gmail accounts are not behaving differently, they are behaving the same by requesting 2-step verification from our phones. Outlook is working fine and not now constantly requesting passwords. It was only the setting up of my wife's gmail account on Outlook that didn't need an app password . . .

Nevertheless, as I said before, this is a Google problem, not Microsoft's . . . but have read quite a few articles and most simply say, "Turn off 2-Step Verification." However, as you say, that will cut off Outlook, which is requiring it. Many even suggested using Edge instead of Chrome . . . "the 2 small boys fighting over a ball in the playground" again . . . but logging into gmail on Edge still requests 2-Step Verification.

Therefore, I was hoping that you may have had a fix because you use "Logic" and have far more experience than I and most of the idiots who seem to have an axe to grind or a blind preference for one of the systems over the other (thankfully, we haven't included any Apples or Big Macs in the menu!!!!)

Anyway, hope this clarifies,

John

PhilC8:

As I said, and really meant, "hijacking" is not a problem!!

.......

. I couldn't believe the absolutely incredible improvement to the 1st PC . . .

Wholeheartedly agree with that - I stopped using HDD in favor of SSDs years ago. Alsa iwouldn't argue with the benefits of a clean install - lots of benefits to that but doing it simply in hopes of fixing an Outlook issue - would never suggest the nuclear option as a first step.

Your Questions:

#1 - Does this involve one computer or two computers in terms of the behavior? Actually four (2 PCs and 2 Laptops). As far as I can tell, it seems to be happening equally on all of them (given that my wife is now complaining about something else, rather than me!!!!)

..............................

John

Since I haven't recently accessed a GMail account using 2FA, going to take a timeout and run some tests in terms of browser access with 2FA enabled using both Chrome and Edge and see where I end up. It's going to take a little while due to other commitments but will come back here with the reults when I'm done testing this (and anything else I find out along the way)

Hi John,

The PC is not that old, perhaps 5 years now and came with windows 10 and is 'quite good' inc a hybrid ssd/hdd. As a man of some vintage however, I would rather have liked to be able to buy one that you can easily replace the battery in and didn't have silly snap on key tops on the keyboard that started popping off about 1 week outside its 1 year warrantee. We come from the days of 'Make do, and mend!' All this I must have the latest gizmo thing has long since past

Getting to grips with No WIndows install Code with a commercial laptop was ... err.. interesting but I did find out how to read that out form the machine, just in case. No install media with the PC (its an HP) was another thing. All these things seem aimed and deliberately making users have to bin perfectly good kit and highly wasteful. I could say things about WIndows 11 which MS say will not update on a bigger tower PC WIndows 10 for my music recording. We wonder at the waste of materials and resources.

I have done the nuclear wipe and reinstalls 4 times on the Laptop following horrible things happening after windows updates that messed up audio devices used with my amateur radio gear. But that was with setting up the old POP3 simple link to Gmail its the lack of stepwise information with these new 2 factor things, combined with pairing hardware/software between different digital ecosystems that are outside our control and where until Karl I have not found support.

Karl,

I worked through the points you raised.

#1 - Yes I configured the new Gmail account login AFTER having deleted the old Office 2010 account that was a POP3 login.   So from what you say

the new account must be in the original, or relic Outlook 2010 Profile.  Understood that I can't have both types POP and IMAP account at the same 

time.

#1a  -   Yes I view the <File>--<Account Settings>--> <Data Files> tab and I have TWO listed

         - first in the list in the new IMAP Gmail account which DOES NOT HAVE a Tick mark

            next to it and it Named as my email address and located in C:\User\username\appdata\Local\Microsoft\Outlook\ with the file named

        as myemailaddress.ost

         - Then there is second Named as Outlook Data File in C:\User\username\appdata\Local\Microsoft\Outlook\Outlook.pst.  NB:  This has a 

       Tick next to the Name.  

#1b  - Noted about the way IMAP uses its own set of folder.   It makes things a bit messy for backing up my mail files vs the old single .pst file.

       So currently (in this mess) I copy from those folders back to the original Inbox, Sent and other locations which I hope are in the .pst file.

#1b  - Your screen shot of the IMAP acocunt settings on my PC matches that image with the exception of the 'Purge items when switching folders

       while online' which is NOT checked on my setup.

#2 - Missing Images 

     -  I have gone through the 'Trust Center' settings a number of times.   The 2 highlighted red boxes 'Don't download pictures automatically...' and '

    Don't download pictures in encrypted or signed HTML...'  are NOT ticked.    All the boxes between these two are ticked but greyed out.   I do 

    not have, and have never setup any specific trusted sites., which is another feature I think.

    So as I understand it pictures should download.   I found other help pages before for this, but toggling these settings on and off, with and with

    out closing outlook and rebooting etc. seems to make no difference.

Today as I had done the SFC.exe and Office Modify > Repair etc. and rebooted I sync'd my gmail.   All my mail came down BUT still embedded 

images were shown as place markers and as before I cannot right clock on those place holders and use the old popup menu that was in 

Outlook 2010 and allowed me to download images.  The option simply is not listed in the popup menu.

From your statements, it looks like I need a NEW Outlook Profile....  please excuse me if I feel a bit apprehensive about that as I fear the hassles

of getting Outlook and Gmail 2 factor authentication to either stay in agreement and I dread that process. This perhaps what the chap in my

other thread was suggesting by saying I had a corrupted install of outlook I don't know, as this time he was saying that it wasn't ... it was just

boggling.

I hope this information is clear enough, sorry I would have uploaded edited images but as I say I don't use online storage to do so.

Thank you both for your kindness, help and encouragement.

Phil