Outlook 2016 repeatedly asking for Password for gmail account

...........I have been side tracked by domestic 'duties' today.

Something we all have to deal with 😊

Question 1 - I don't fully understand the difference between .pst and .ost.   I take it .ost files are only used for IMAP email access, is that correct 

please?

a) OST files are used by IMAP and Exchange accounts to be technically accurate

b) OST and PST are Outlook data files with a significant difference

c) a PST (personal storage) file can be associated with a POP account OR it can be a standalone data file not associated with any POP account. A PST file can be opened on its own by any version of Outlook.

d) a PST file never automatically gets removed from an Outlook profile. To put it another way, if you remove a POP account, the PST file associated with the account remains in the Outlook profile. until if and when it is manually removed.

e) an OST (Offline Storage) file is specific to the email account that was used to create the file. In short, you can never take an OST file and use it in another instance of Outlook. Another way of putting this is that an OST file can only be opened by the original Outlook profile and original email account used to create it. If the email account is removed and then re-added to the same Outlook profike, a new OST file is created.

f) when an IMAP or Exchange account is removed from an Outlook profile, the OST file associated with it is removed from both the Outlook profile AND the system - the file is gone.

g) when an IMAP and Exchange account is configured, Outlook syncs the data with the server for the email account. For IMAP, that only includes email folder. For Exchange, everything is sync'd with the server (email, contacts, calendar etc)

Question 2 - Would a clean install using IMAP email have created and used the default .pst file without a .ost file.

Short answer: No - not possible. IMAP accounts do not use PST data files.

this is all very scary as Google simply do not reply on their site and the help 

files are not that good for the likes of me.

May I offer some friendly advice? Well. I'll offer it without your answer 😊

Put all your fears aside, take your time going slow and easy when you go through things. If you stick to the steps provided, there is no way you will irreparably hurt anything. That and follow something I'm a firm believer in "measure twice - cut once" - in other words, not sure about something, just ask <before> you do something, not after.

Let me put this another way, it is far simpler then how all of this may appear but I'd be lying to you if I said that I never bang my head against the wall doing some "easy" stuff. Everything is "easy" once you know how to do everything. When that happens, time to step back, take a deep breath (or three) and go at things again. Frustration (and trying to rush through things) is a deadly enemy and can easily lead to mistakes.

I am used to configuring the Outlook POP account settings but will have to find out what the server details and Port numbers are for Gmail again.

I assume they will be different to those that I had before in Outlook 2010 but, maybe not.

I cannot say that I recall seeing box highlighted 'Message Delivery Area' in account settings in O'2010 and of course I didn't manually configure

this in O'2019 hence I ended up with IMAP.

• Email account settings are the same no matter what email client is used, the <email client> makes no difference in terms of the actual account settings. The only difference between different <email clients> (i.e. Outlook '2010, and Outlook '2019 i this case) are the actual steps you follow to enter the account settings = the settings themselves don't change. In short, the same Gmail settings apply to both '2010 and '2019 (leaving the <App Password> requirement aside for the moment.
• About email configuration using the Control Panel Mail app / Outlook '2010 / Outlook '2019

The Control Panel Mail app and Outlook '2010 use the same email configuration UI. Starting with Outlook '2013 thru to today ('2021 '354) a new UI is used when an account is added from within the Outlook app itsself (i.e. <File> --> <Add Account>) - just a different UI to get the same thing sone. The old UI provides more granular control over some settings.

• If only the email address / password is entered to configure an email account, Outlook will configure the account using IMAP by default (or Exchange when applicable as in the case of an Outlook.com account as a for instance), This done through a process called <auto-discover> where it interrogates the server to get all the necessary settings (i.e. server name, port #'s, encryption etc)

Regardless of which version of Outlook is used, a POP account MUST be explicitly manually configured and all settings entered individually

#Images Issue

If you are at a loss on this, then that is a worry, I think in modern parlance it's a case of <eek>, given the expertise and patience you have 

given us.

Question - How do I ensure that I do not delete my existing 'Outlook Profile'?     Is this the .pst file or something else?

Will only be at a loss after you have tried everything and it still doesn't work. Have a ways to go before I get to that point

As for "knowing how to ensure that you're not going to delete the existing profile" - that will become obvious when you actually start to go through things but a safe rule is if you're not sure about something, stay away from buttons labeled <remove> <delete> etc 😊

I am reading and rereading the notes on accessing the <Control Panel> and <Mail (Microsoft Outlook) (32 bit)> on windows 10.   

I can see the name of the existing profile 'Outlook' on the Laptop.

I haven't yet had the nerve at this hour to go and delve in Gmail to work out what I need to do to get the <App Password> and if necessary delete the existing IMAP link?

I will have a look at that tomorrow as I fear I may make a mistake being to hasty.

Thank you so much for your help Karl.   I will update when I can, I hope tomorrow.

Phil

As mentioned, just take it slow and easy and actually start doing things. It really is a lot easier then it may look. Reading is a good thing but reading while you are doing is even better. When in doubt, just stop and ask - can't get any simpler than that. When it's all over, you'll be asking yourself why you worried about it so much 😊

Start with this

#1 - Open the Control Panel Mail app

#2 - Just click on everything (other than a <remove> button) to see what everything does especially the <Show Profiles> button. If you create a new Outlook profile, doesn't impact anything - you can create as many Outlook profiles as you want and you don't have to use an Outlook profile that you have created. I have all kinds of different Outlook profiles I've created / used for testing different things as shown in the screenshot

*** when creating a new profile because the original is suspected of being corrupt - NEVER take the lazy approach of using the <Copy> button, start fresh so as to not carry over any possible corrupt from the original profile. Copying a profile has its uses but not for trouble-shooting.

Hi Karl,

Please forgive my slow response.   I have been side tracked by domestic 'duties' today.

Ok on the uninstall not removing my old O'2010 profile and .pst file.  I usually backed up the .pst file to a portable HDD just in case of horrible 

things. None the less, I follow the logic though I didn't really know where MS stored profiles or thought it may have been a registry entry.

Question 1 - I don't fully understand the difference between .pst and .ost.   I take it .ost files are only used for IMAP email access, is that correct 

please?

Question 2 - Would a clean install using IMAP email have created and used the default .pst file without a .ost file.

You are correct there are no contacts or other folders in the added gmail account folders and I do not store my contacts on gmail servers either.  

It's kind of a courtesy thing to my contacts in case google are 'hacked' and those details used.

I am reading and trying to digest your guidance so that I can switch back to POP access as I think I liked that far more and knew where I was, at 

least as you say 'image problems aside'.  That and navigating the process with Google and my account in a way that gets me an <App Password>

and whatever I need to do to terminate the existing IMAP details....  this is all very scary as Google simply do not reply on their site and the help 

files are not that good for the likes of me.

I am used to configuring the Outlook POP account settings but will have to find out what the server details and Port numbers are for Gmail again.

I assume they will be different to those that I had before in Outlook 2010 but, maybe not.

I cannot say that I recall seeing box highlighted 'Message Delivery Area' in account settings in O'2010 and of course I didn't manually configure

this in O'2019 hence I ended up with IMAP.

#Images Issue

If you are at a loss on this, then that is a worry, I think in modern parlance it's a case of <eek>, given the expertise and patience you have 

given us.

Question - How do I ensure that I do not delete my existing 'Outlook Profile'?     Is this the .pst file or something else?

I am reading and rereading the notes on accessing the <Control Panel> and <Mail (Microsoft Outlook) (32 bit)> on windows 10.   

I can see the name of the existing profile 'Outlook' on the Laptop.

I haven't yet had the nerve at this hour to go and delve in Gmail to work out what I need to do to get the <App Password> and if necessary delete the existing IMAP link?

I will have a look at that tomorrow as I fear I may make a mistake being to hasty.

Thank you so much for your help Karl.   I will update when I can, I hope tomorrow.

Phil

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!!!!)

Hi John

Don't think you are going to like this answer <g> - results from a quick test

#1 - So I turned on 2FA on one of my Gmail accounts

#2 - First, opened Chrome - went to my account n problems - was previously signed into the account from previous activity on the account on days gone by - went straight in

#3 - Then did the same thing on Chrome - same deal as #2

#4 - Then signed out of the account (using Chrome) and went to sign in and had to go through the 2FA second factor verification - no problem - got into my account

#5 - Closed the browser without signing out of the account

#6 - Started Chrome again and went to my account that was I logged into in step#2 - went straight in with no need for verification. (Did that a few times to t make sure of what I was doing)

#7 - Launched Chrome in incognito mode (twice) and each time I need to log in and verify via 2FA which is what I would expect it to do

Notes:

a) I don't explicitly log out of the Gmail account before closing the browser or the Gmail page (I usually have a bunch of tabs open at any one time)

b) I have both browsers set to remember passwords

Long story short - everything works like a charm as expected with no need for repeated 2FA verification on repeated access to the account on the same machne. I would expect this to be the same on my other machines with the first time requiring 2FA verification

OK - let's go through things - piece by piece

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.

All of the above is easily explained. When you uninstalled '2010, it did not remove the Outlook O'2010 Outlook profile. When you installed '2019, it copied the information from the '2010 Outlook profile which would have included the data file info (ergo - the PST file). When removing a POP account, it does not remove the PST file associated with that account which is your case is a really good thing. The <default data file> is where the default contact / calendar folders are stored.

Just for info, in case I haven't mentioned this already, if Outlook cannot find / open an OST file, it will automatically create a new one and sync with the server. In the case of an IMAP account, that only includes email folders. If the OST file was set as the <default data file> - the "this computer only" contact / calendar folders would be empty (ergo the data in the those folders would be lost. Another info tidbit, if there is an existing <default data file> in the Outlook profile <before> you configure an IMAP account, you will not have any contact / calendar folders in the IMAP folder tree just in case you're wondering why you don't have any,

So..........there is no requirement to have your Gmail account configured using IMAP, you can just as easily configure it as a POP account, just like you had with '2010 AND you can use your existing PST file for the account so nothing gets lost and you can keep on working the way you were used to which probably would make things a lot easier for you (image problem aside). The only thing is that for a POP account, enabling 2FA in Gmail is mandatory along with generating / using am <App Password>. All that info is outlined in my response that was marked as "the answer"

In '2019, a POP account must be explicitly manually configured which is done by

a) click on <Advanced Options> underneath the email address box when you add the account

b) check the box for "Let me setup my account manually"

c) click on <Connect>

d) select POP and proceed accordingly making sure to select an existing PST file instead of letting Outlook create a new one.

Now - people have reported that there are instances where the option to select an existing PST file is not provided. Not a problem, that is something that can be resolved after the fact but will leaebe that to another message if it's necessary.

#2 - Missing Images 

From everything you've described so far, have to be honest, am at a loss to isolate a specific cause for this behavior. This is what I would do if it were me but before that, let me ease your concerns about creating a new Outlook profile, as long as you don't delete the existing Outlook profile, you can always go back. Absolutely nothing would be damaged by doing this. You can create as many Outlook profiles as you want.

You might even want to try your hand at configuring the account as a POP account. It's unfortunate that you deleted the POP account in this process since all it required was changing the password for the account to use the <App Password> but no matter, just as easy to get back there.

First step is to take note of the full folder path / file name of the PST file in the current Outlook profile as listed under <File> --> <Account Settings> --> <Data Files> tab

With that in hand, 2FA enabled for the Gmail account and an<App Password> generated, time to create a new Outlook profile. Somewhere in this thread I think I included these steps but for convenience will do it again

a) - With Outlook closed open the Control Panel <Mail> app

Just in case you need info regarding how to access the Control Panel Mail app, that's described in the following article by Outlook MVP Diane Poremsky

Where is the Control Panel Mail icon?

https://www.slipstick.com/how-to-outlook/where-is-the-mail-icon/

If using Windows 11

How to Open Control Panel in Windows 11

https://www.lifewire.com/open-control-panel-in-windows-11-5193187

b) - Select <Show Profile> --> <Add> --> give the new profile a name (no need to remove the existing Outlook profile)

c) - Configure your email account(s)

be sure to use the existing PST file for this account but if the option doesn't appear for you, don't worry about it, go with the flow and just let me know. Will provide you with the steps on how to go about using the existing PST file

d) - Set the newly created Outlook profile as the default for the next time Outlook is opened otherwise it'll use the old profile

Now if you got everything set up and you still cannot get your images downloaded, and the boxes in the Trust Center are unchecked, the next thing I would do is a repair of Office '2019

<Settings> --> <Apps> --> <Apps & Featires> --> scroll down to <Microsoft Office 2019> --> click on <Modify> --> select <Online Repair>

Will stop it here for the time being for either any questions you may have or to find out what the results are in terms of the steps outlined

One last minor point regarding

.......sorry I would have uploaded edited images but as I say I don't use online storage to do so.

Don't need online storage to capture and include screenshots but doesn't matter - none are required. Got everything needed from your description