Outlook 2016 repeatedly asking for Password for gmail account

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.

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.

Going the nuclear route (wiping your PC) would be extreme and unnecessary if the only reason is related to Outlook.

Another tidbit you should be aware of is that when you uninstall Office, the Outlook profiles are not removed so when you reinstall Office, Outlook will continue to use the same Outlook profile - hence making the whole exercise a waste of time if the objective is to start over with Outlook.

As a FYI - how to "start over" with Outlook, would be to use the Control Panel Mail app

a) - With Outlook closed open the Control Panel 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) 

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

In reference to reinstalling Office '2019 (any current version of Office - '2013 and later)

Office is associated with a Microsoft Account. To download / install Office again, that's done by

#1 - Log into the applicable Microsoft Account --> click on <Services & Subscriptions>

#2 - Download and install

This link will get you there

Microsoft account | Services & subscriptions

For perpetual (one time purchase) license (any version of Office designated as <Office 20##>, if you encounter an activation error, would need to follow the steps contained in the following article under the section

<Activate after reinstalling or moving Office>

Activate Office using the Activation wizard

https://support.office.com/en-us/article/activate-office-using-the-activation-wizard-1144e0de-e849-496e-8e33-ed6fb1b34202?ui=en-US&rs=en-001&ad=US#bkmk_phone

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.

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