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

Don't know if you're following my thread that you moved to OneDrive a few days ago,

Reply is in that thread. In case anyone else is following this, that thread is

OneDrive questions/issue - Microsoft Community

Hi Karl,

Don't know if you're following my thread that you moved to OneDrive a few days ago, but now that we've cracked the Outlook password issue (except in Edge) I've been able to look into the OneDrive issue again and have just posted.

Am seriously thinking of upgrading to 365 and switching from Google Drive to One Drive, except for gmails.

The post has a specific question re Outlook .ost files and I would be grateful your opinion on that and any other questions that you may be able to address.

Many thanks,

John

1. Does making\creating a new profile using the <Control Panel> <Mail> create a new .pst file or does it use the existing .pst file?

Creating a new profile, in and of itself, does not create any data files. All that magic happens when you configure an email account. In the case of a POP account, it would look like this when configuring the account using the Control Panel Mail app

2. I looked at my Gmail Account settings, specifically looking at the <security> settings to see what was there and that raised a few more questions. Note in the image (yes I learnt that too) that even though I used the wizard to get the IMAP mail account setup (which works, subject to images), it didn't seem to switch on 2FA despite that being a major forced change to Gmail access, I'm puzzled?

Not quite clear about what you are asking / referring to in terms of "I used the wizard to get the IMAP mail account setup (which works, subject to images), it didn't seem to switch on 2FA"

You need to turn on 2FA manually and follow the steps before adding anything to Outlook (any version) as a POP account (that said Outlook '2019 doesn't need 2FA / App PAssword for an IMAP account

3. If I switch on 2FA on Gmail settings which I would have to do to create an <App Password>, I am now wondering if that will break the existing, albeit not quite right due to images, IMAP settings I have or worse impact what happens on my Android (phone) mail client? If I lost that phone access I would be truly scuppered at the moment. I realise this is a GMAIL area, but I have not found their help areas very good,. I may be taking you beyond what you feel comfortable to answer?

4. My current IMAP settings see below are according to Gmail basic, this was created by the wizard in June.

I have not found if this 'basic' access maybe what is preventing images? (probably not).

As mentioned, you will need to generate an <App Password> if you are going to connect the account to any other <email client> as a POP account. Know of no reason why using 2FA impacts anything to do with images