Outlook 2016 repeatedly asking for Password for gmail account

Hi Karl,

I don't know how to lift quotes from your post, so I will endeavour to stick to the point and work through your questions;

1. The issue is that whilst Outlook 2019 will connect to my Gmail account and send and receive emails. Two things have happened;
   • Any emails sent to me that include images or are HTML based with images, no images download.
   • After sorting out the Gmail 2 factor authentication (I used Outlooks wizard thing) it created a separate set of folders for that account.

Of these 2 issues, the worst failure is that I cannot right click on image placeholders and use the old 'download images' popup option as it does not appear in the popup list and no changes to Trust Center settings seem to have fixed outlook to get the images to download.

Secondly, whilst I can manually copy mails (sent and received, minus images I should have received) in Outlook from the newly created Inbox and other folders to the core Outlook Inbox where my old mail was (in the .pst file) it is a pain to that. If I have to, I can live with this second issue but I like to keep my post in a single .pst file if I can and the pictures thing is killing Outlook and my mail use.

2. Did I create a new Outlook Profile?

Good question! As I stated above outlook seemed to find my old posts, but I had to create an account Login (did that create a new profile or corrupt an old one I have no idea). I used the create account in Outlook to login to Gmail and it used my gmail address and password and went through a wizard type of process with Googles gmail server to create it. That created an IMAP account where previously I had had a POP3 account. It also created the separate subset of folders in Outlook as I said. I hope that is enough as frankly 'Profile' or 'Account' may be the same.

#1 No I definitely used the proper MS Office 2010 Pro uninstall feature before I installed Office 2019 Pro. I also made sure I rebooted the PC before I proceeded to install Office Pro 2019.

#1a I have since then used SFC.exe to check and fix any system files.

#1b I have also used Windows\Settings\Apps\MS Office 2019\Modify\Repair

#2 As I say I am not enthusiastic about the Nuclear option either.

#3 Expanding on the 'Cycle' comment I made. I think I have covered this really in the answers above. As I say, the account will connect and send/download emails subject to the issues I gave in may answers in (1) above.

I hope that I have laid out things in a clear and neat enough way and with enough detail. I have done my best to recall and present accurately, but I actually did the install and connect to Gmail back in June or July when they imposed their 2 factor requirement.

Thank you again for your kindness and patience.

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

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!!!

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 😊