Outlook Keeps Asking for Password

I use Microsoft Outlook (Office 365 2016) for email and for the past several months, it's been asking for the password for various of my email accounts.

After awhile it will accept the password, and everything will be fine until something breaks again and the process starts all over.

I'm not sure, but it may have something to do with my VPN. Until yesterday, I used VPN Unlimited, but it just wouldn't stay connected, and I thought that may be Outlook's problem.

So I changed to Windscribe VPN, but I'm getting the same old same old; now I'm getting emails about suspicious activity from a long way away from me (which makes me suspect a VPN).

I'm about to go crazy with this; every few days, Outlook refuses to accept my legitimate password on a particular account.

For some odd reason, my @ Live and @ Hotmail accounts don't seem to be affected; only my @ Outlook.com.

Anybody have any idea what's going on?

VPN could be the culprit, but then.. @live and other mail aren't affected.

- Outlook got some beta functions lately. You can turn them off (right top corner, when you go to Outlook online)
- check how many devices you have (click on your picture.. account... connected devices. Delete the ones you don't use any more.

Check in Outlook, if checkbox for requesting credential isn't checked. This is part of Outlook data file (under account settings)

Wynona, here is one MS document about Outlook and asking credentials.. See, if it helps.

support.microsoft.com | /en-us/help/312630/outlook-continues-to-prompt-you-for-logon-credentials

Did this solve situation?

Sorry, I've been offline since about 1:00 and haven't seen these replies yet, Andre and Ken.

I have to leave for pool league tonight, but will work on these when I get home or in the morning.

Thanks,

Did Andre's suggestions work?

Update:

I now know that it's the VPN that's causing Outlook to lose its mind over my passwords. This morning, I logged on before Windscribe had a chance to connect and I got my email on every address.

So, I closed Outlook, turned on Windscribe, let it connect and opened Outlook; it could not remember my outlook.com email client passwords.

I closed Outlook, turned off Windscribe (both the IP address and the firewall), then opened Outlook. Without a hitch, Outlook downloaded my emails!

So, now I know what the problem is, but not how to fix it. I'm going to follow Andre's instructions next to see if that makes a difference.

AndreTen said:

VPN could be the culprit, but then.. @live and other mail aren't affected.

- Outlook got some beta functions lately. You can turn them off (right top corner, when you go to Outlook online)
- check how many devices you have (click on your picture.. account... connected devices. Delete the ones you don't use any more.

Check in Outlook, if checkbox for requesting credential isn't checked. This is part of Outlook data file (under account settings)

Andre, I can get as far as Account Settings, but not to Where you are. Here's what I see in Account Settings:

When in account settings, / select data files / select account you want change (outlook.com) / click Settings / check security

Another thing.. We will have to check your firewall settings...

I have the same settings, Andre.