Outlook 2016 repeatedly asking for Password for gmail account

Hi Karl,

You're right I didn't like your response, ha ha! but, between the lines, it told me that my problem probably had to be a default setting that normally wasn't important but wouldn't work with 2-step verification turned on. This thought spurred me into seeking a solution under every mat and behind every door in both Windows and Chrome until I went boggle-eyed.

However, it appears that, finally, I may have cracked it on my main PC and my laptop . . . but, embarrassingly, as I had changed so many settings, I can't tell you specifically which one worked, nor whether it was a setting in Windows nor in Chrome. Herewith, screenshots of just 3 of the settings that I "fiddled with" . . . when I say fiddled with, I mean that I toggled them repeatedly on and off and constantly logged out and back in again, including restarting the apps and the devices:

(1) Windows

(2) Google Chrome:

(3) Google Chrome:

The most annoying thing is that these 3 at least are all set exactly as before I started fiddling.

However, something seems to have worked, so I'll keep fingers crossed.

Kind regards,

John

...........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