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.

I didn’t mean to Hijack Johns request for help. I had started a request here

https://answers.microsoft.com/en-us/outlook\_com/forum/all/outlook-2019-pro-on-windows-10-how-to-fix-corrupt/5a6456db-4db2-4677-b164-3228afc6eeef

The person replying is sadly confusing me and contradicting what he advised back in June when I tried to fix things when it all went wrong. It’s taken months to pluck up courage to try again.

I am not sure what to do, the nuclear route as you called it does seem extreme and would take ages as well as the fact it may not workout if I hit more problems that I can’t resolve. So I am apprehensive of trying it.

Thank you so much for you helpful pointers.

Have read through your other thread so let's start from the beginning so that we are both on the same page as tp what the exact issue is that you are trying to resolve today. Also, please indicate whether or not you have created a new Outlook profile at any point in your trouble-shooting process

Other comments

#1 - If you uninstalled '2010 after installing '2019 then would definitely recommend doing a <Online Repair> of '2019 just to make sure that everything is set correctly

<Settings> --> <Apps> --> <Apps & Features> --> scroll down to <Microsoft Office 2019> --> select <Modify> -->Online Install>

The <online repair> is actually an uninstall / reinstall of '2019. If for any reason the reinstall does not complete which sometimes happen in rare cases, the solution is to log into the Microsoft Account --> click on <Services & Subscriptions> --> download / install. This link will get you there

Microsoft account | Services & subscriptionsggest

#2 - As for the nuclear option, wouldn't be something I would suggest from everything I've read to date. Would be a painful and needless exercise that likely would not resolve anything that couldn't otherwise be fixed.

#3 - Regarding

>>

If I cycle a synchronisation with Gmail, sadly I cannot retry getting any emails downloaded if they don’t first arrive with the images, even though I leave copies on the server. At least I know of no way to get them again.

<<

Can you expand a little on that? Specifically, (1) is this account configured as a POP or IMAP account and (2) not clear about "cannot retry getting any emails downloaded?

To confirm how your account is configured, from within Outlook, go to

<File> --> <Account Settings> --> <Email> tab

Once the above info is provided, will go from there

Karl,

Thank you very much for your kind and informative reply. I followed the instruction to find the ‘old fashioned’ windows control panel in windows 10 and could find an entry for

Mail (Microsoft Outlook) (32-bit)

I could open that and it gave a number of options.

Under Profiles it only has one ‘Outlook’ showing on a General tab

Under accounts it has 1 showing setup as my email and IMAP/SMTP (send from this email by default)

Under Data Files it has 2 entries one as my email address in AppData\Local\Microsoft\Outlook*emailaddress.ost*. And the old Outlook 2010 entry called Outlook Data File in Users*username*\Documents\Outlook Files\Outlook.pst

The old Outlook.pst is what I kept as it retains my email history sent and received and I have been moving the gmail I received into those folders to try and retain that history. However, no emails with images attached/embedded download with the images anymore. Nothing I have tried has fixed that. Those attempts have been repair settings in outlook, checking and cycling the Outlook Trust Center settings to download images. I also tried Using SFC.Exe to repair system files and from the Apps section of windows 10 settings the Modify and Repair feature for MS Office.

If I cycle a synchronisation with Gmail, sadly I cannot retry getting any emails downloaded if they don’t first arrive with the images, even though I leave copies on the server. At least I know of no way to get them again.

I didn’t mean to Hijack Johns request for help. I had started a request here

https://answers.microsoft.com/en-us/outlook\_com/forum/all/outlook-2019-pro-on-windows-10-how-to-fix-corrupt/5a6456db-4db2-4677-b164-3228afc6eeef

The person replying is sadly confusing me and contradicting what he advised back in June when I tried to fix things when it all went wrong. It’s taken months to pluck up courage to try again.

I am not sure what to do, the nuclear route as you called it does seem extreme and would take ages as well as the fact it may not workout if I hit more problems that I can’t resolve. So I am apprehensive of trying it.

Thank you so much for you helpful pointers.

Karl,

Thank you for that 'nugget' of information I have copied it to a rtf file in case I summon the courage to wipe my Laptop and reintstall everything. I am anything but confident of doing that as I don't know if using windows 10 reset and reinstall will force windows 11 (which I don't want) or that I can actually work out how to re-install Office Pro 2019 even though it would be on the same PC because WIndows installs change all the PC name etc. and there is nothing that tells old folk like me that what to do. So it risk finding that as I've installed it once before I can't install it again even on the same machine. And that would be before trying to sort out how to get the re-install to talk to Gmail..... :(

I have to say that the systems deployed these days are not at all friendly for older people and with no reliable route for support it is becoming more and more ageist and excluding more people from doing anything, even if it was intended to be 'safer'.

Thank you again. I am glad John got a solution.