Outlook office 2016 keeps asking for password for my personal email but not for my company email.

same password prompting issue since the announcement of the Russian hackers into Microsoft's software vaults back in January 2024, either Microsoft does not care or they are trying to forcefully drive the customers in a different direction.

The issues are all coming from Microsoft's side of things. Nothing we can do on our local systems makes any difference. just my 2 cents worth since i've had this password issue and have tried all the suggestions above and beyond required with no solution.

Maybe a class action lawsuit needs to be started with Microsoft over this issue. Anyone else have this feeling? Anyone know how to start one?

This did not work. I think it worked for about 10 minutes, then a reboot of laptop and its back to frequent password prompts. I am curious, has this worked for anyone else?

Hi,

I was suffering the same problem, but for me it doesn't look like an issue related to local machine instalation or configuration, it's more related to a 2FA matter.

I decided to enter to OWA to check the security configuration to see if there is some section related to the approved devices or some else.

The surprise was when I entered the login credentials on the OWA it asked me the 2FA (I have not configured any 2FA in my account). I had to validate from my outlook mobile app and not from the microsoft authenticator app. After that Outlook 2016 has never asked me for the password again.

So, those are the steps that worked for me:

• Have the outlook account configurated in the Outlook mobile app (Android in my case)
• Login to: https://outlook.live.com from your computer. It asks for the 2FA authentication.
• Validate from your oulook mobile app.

I hope it helps.

Thank you.

Hi,

I was suffering the same problem, but for me it doesn't look like an issue related to local machine instalation or configuration, it's more related to a 2FA matter.

I decided to enter to OWA to check the security configuration to see if there is some section related to the approved devices or some else.

The surprise was when I entered the login credentials on the OWA it asked me the 2FA (I have not configured any 2FA in my account). I had to validate from my outlook mobile app and not from the microsoft authenticator app. After that Outlook 2016 has never asked me for the password again.

So, those are the steps that worked for me:

• Have the outlook account configurated in the Outlook mobile app (Android in my case)
• Login to: https://outlook.live.com from your computer. It asks for the 2FA authentication.
• Validate from your oulook mobile app.

I hope it helps.

Thank you.

I just noticed while Outlook 2016 was open, and it said in the bottom right corner "Connected to Microsoft Exchange", the "Windows Security" password prompt dialog window popped up. I scratched my head wondering why it would be prompting for a password if it is already connected..?

As a test I sent an email (1st) from my Gmail account to the Hotmail account that the dialog window was prompting for a password. Interestingly the sent email came in to the Inbox for the Hotmail account without my need to enter the password.

I tried to reply to the email from the Hotmail account to the GMail account and the email was stuck sitting in the Outbox.

While the reply email sat in the Outbox, not being sent, I went to my GMail account and sent a 2nd email to the Hotmail account. Again the email came into the Hotmail Inbox like the first one did, all while the 1st reply email stayed in the Outbox not being sent.

I then sent a 3rd email from the Gmail account to the Hotmail account, and that too came into the Inbox of the Hotmail account, all while the first (1st) reply from Hotmail back to the GMail sat not being sent in the Outbox.

Hmm ..? What's happening with that? Any ideas?

Emails come in, but nothing leaves. After the 3rd email test that came in from the GMail to the Hotmail account I finally Entered the password into the dialog window for the "Windows Security" pasword prompt. After entering the password, the reply email for the 1st email from Gmail was sent from the Hotmail account.

Does Microsoft's Exchange configuration for Hotmail in Outlook 2016 have a Incoming and Outgoing Server name somewhere?

When configuring the Hotmail account originally the setup never prompted for Incoming or Outgoing server names, and just Auto Configured itself to connect to Microsoft's Exchange services. It is like Outlook is waiting for credentials for Sent items, but not for Recieved items?