Outlook 2016 repeatedly asking for Password for gmail account

#1 - <App Password> does not time out. Just make sure you don;t turn off 2FA after generating the <App Password>

#2 - <App Password> is a 16 char contiguous value (no spaces)

#3 - As far as Outlook.com POP goes - same process with different values but you enable POP access for the account

#4 - These are the visual steps to add a Gmail POP account (any version of Outlook - makes no difference if using Outlook '2010 or earlier or adding it using the Control Panel Mail app)

Step #3

a) enter the name and email address

b) select POP and enter the server settings as shown

c) enter the 16 char <App Password> as the password for the account

d) decide whether you want Outlook to create a new PST file for the account or select an existing PST file

Step #5

a) set values as shown

b) decide whether you want the messages removed from the server after being downloaded from the server

c) click <OK> --> all done

If the above steps don't work for you, then there's nothing more that can be suggested. Would mean there is an issue with your system

Karl,

I found the microsoft account layout and what was presented so confusing I have absolutely no idea.

The instructions that came with the licences said they could only be used on 1 pc. It installed and activated when I first installed it but what the hell goes on behind in internet land is not visible at that time, its not documented and I have given up with it.

Can relate to being upset with somethingbut that really should be directed to the right place

#1 - Re: not sure what exactly is deemed to be confusing in terms of licenses associated with a Microsoft Account using the link I provided which would look similar to the attached screenshot

Microsoft account | Services & subscriptions

#2 - As for redeeming a legitimate product key, those steps are contained in the following. Can't speak to whatever the reseller provided you with

Where to enter your Office product key (microsoft.com)

In any case, hope you get everything going with '2010 and get back to more productive activities

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>

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