Outlook 2016 repeatedly asking for Password for gmail account

Hi Karl,

I don’t quite understand the two systems and how they work. I thought That Google switched on 2FA as default when they made changes in June. Certainly my old O’2010 POP login ceased working saying that it could not get password to work. At the same time Google sent a warning the Outlook versions prior to 2013 version would no longer work with their login.

So, when I say ‘wizard’ (an old MS term in office I know) I mean that I went into Gmail and told it I was going to connect with an MS product (I am sorry I can’t recall how I did that, maybe it gave me a password…. My mind is a fog on that) as there was no application pairing on my Gmail account. Then I used the create account feature but did Not use the manual setup. I say this because I cannot explain why my Gmail account was not showing 2FA as switched on (in the image I uploaded) either that or it is a redundant setting in my Gmail account, I just don’t know or understand it.

My guess is that by not using manual setup in Outlook, the process defaulted to IMAP hence it created the .ost files and I didn’t get to choose using the existing data file. I feel, really stupid now that I simply can’t remember the missing detail.

If creating a new ‘profile’ does not create a .pst then I am assuming the ‘profile’(s) is/are stored in another Outlook system file or as a dreaded Windows registry entry set.

Based on where we are, the idea of creating a new profile is to fix any cross/corruption in the existing profile that is preventing embedded email images downloading. Certainly the profile I have ‘was’ set not to download embedded images as a default when I was accessing via POP account settings. Perhaps the O’2019 process has corrupted the original profile in some way. Quite why toggling the settings to restore the download on images does not fix it can only be explained as a ‘bug’ in the package at this point. There have been many posts with users suffering the problem but as yet I have never read one with a solution.

I will have a go at; saving my current .pst as a backup, delete the Gmail App pairing in my Gmail account, create a new outlook profile and then reset up access to Gmail using the new outlook profile. Ideally, If it works, I can use my existing .pst file and get things to work into that.

I have somehow stay calm doing it. I am not doing it tonight but when I have I’ll let you know if it works or if it means I have to go nuclear…. Hope not.

Thank you so much for your patience and help Karl.

Phil

Hi Karl,

I hope that you are still seeing this thread, I know its been a few days and I also know that you have been burried in One Drive stuff with John so I took a step back here and was trying to get some Google help with setting on their systems (unsuccessfully).

As you suggested I started to play around with the '<Control Panel> <Mail> features in windows with the intention of setting up a new Profile as you had also suggested. Anyway, I followed the Mail notes that show telling you what to try and use (see first image below), and <Data Files> tab selected the new gmail account files set that was setup, so the first one in that list pointing to the .ost file. ;

I then tried to look at it's settings as the note suggests, and got this;

I am wondering if I am doing something wrong, or if there is an access problem to this set of files that is preventing any Security Center settings I toggle for the images to download being changed. Am I being daft or are those settings actually held in the .pst file which has the tick on it?

Thanks Phil

HI Karl,

I hope you are still seeing this thread.

Since we last exchanged messages I have been trying hard to find out more information on the Gmail Community regarding their account settings.

I am told by one of the Gmail community rated advisors that if I switch on 2FA in my Gmail account and get an 'App Password' for Outlook that it will prevent access to gmail using my mobile phone and the Gmail App.

See here; Is here anybody here who can properly walk through Googles Account App Passwords and 2FA info - Google Account Community

So it now looks like I need to finally go the nuclear route and wipe my PC, reinstall windows and all my software and try again with Outlook 2019.

The question I have now is, is it possible to setup with the IMAP and get it to put my emails into my .pst file instead of the .ost files that sit outside that?

Things used to be ok, now I am just desperately depressed and thinking I will have to switch all my email and contacts to something else and bin Gmail which is a major upheaval with so many contacts and accounts that use my gmail address.

Thanks

Phil

The question I have now is, is it possible to setup with the IMAP and get it to put my emails into my .pst file instead of the .ost files that sit outside that?

I don't use the Android Mail app so can't speak to any of that. Seems odd that it wouldn't work just because you have 2FA enabled - so you're saying that if you use the <App Password> in the Android app - it doesn't work? In any case, not something that I can't get into. What prevents you from onfiguring the Gmail account on the phone using IMAP and POP on the computer with the "Leave a copy of email messages on the server" option enabled.

In a nutshell - a POP account requires 2FA to be turned on and using an <App Password> is required. Gmail allows both POP and IMAP enabled so there shouldn't be a problem configuring the account on the phone.

If you keep the account configured as an IMAP account on the computer an alternative solution is

#1 - Add a PST file to Outlook

#2 - Create an <Inbox> rule to <COPY> (not move) all items arriving in the <Inbox> to a folder in the PST file using the rule action of <Move a copy to the specified folder> as opposed to <Move to the specified folder>