Outlook 2010 Outlook in Windows 10 keeps asking for user name and password repeatedly

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Outlook version
Outlook 2010 32 bit
Email Account
We have, within the past 24 hours, developed an issue with Outlook 2010 in our Windows 10 office PC.

For the past several years, we have used Outlook on the desktop to check out POP3 account on our ISP account. It was set to check for messages on startup, after rebooting and then every 15 minutes. It has worked flawlessly... until now.

It suddenly started launching a pop-up asking for "User Name and Password on the following server" It showed the correct POP3 account, the correct ISP server, correct email, user name and password. The "remember this password" box was unchecked, so I check it and it would do it's thing... until the next 15 minute interval, and it asked all over again for the "User Name and Password on the following server" with an unchecked "remember password box."

I checked the settings and tested the account and everything worked. The "remember password" box was checked... even thought the pop-up shows it unchecked. I checked the Windows Credentials and the Credentials manager showed absolutely ZERO credentials for Web or Windows... Okaaay, is that normal?

I have tried everything I can think of to identify the issue. It's ridiculously annoying to be working and every 15 minutes, have to deal with this pop-up. I eventually went into Settings and unchecked the "check every 15 minutes" box and am waiting to see if it still does the pop-up... I don't trust it.

I am still able to manually "send/receive" which is better than the pop-up but not as nice as the "check every 15 minutes" in the background.

I am hoping there is a reasonably simple fix and someone here can toss me a bone on how to get back to "normal."

There is a known issue like this when Windows 10 upgrades to ver. 2004.
Was there recently a Windows "Feature" update?
There is a known issue like this when Windows 10 upgrades to ver. 2004.
Was there recently a Windows "Feature" update?
I am not sure. I will have to look into that.

Thanks for getting back to me! I will let you know.
Do you have SSL enabled on incoming and outgoing?
and what are your incoming and outgoing ports?
Last edited:
Do you have SSL enabled on incoming and outgoing?
and what are your incoming and outgoing ports?
Thank you for the response.

Incoming POP3 995
Outgoing SMTP 25
Yes... SSL box is checked.
Try changing the outgoing to 465.
Changed Outgoing to 465.
Tested the settings and got the following message:
Send test e-mail message: The connection to the server was interrupted. If this problem continues, contact your server administrator or Internet service provider (ISP).

Reset it back to 25 and it works for a manual Send/Receive.
Try changing the outgoing to 465.
Okay... I am not an Outlook Einstein, but I reset the Outgoing back to 465 and exited Settings.
I composed a simple message to my disposable Yahoo account ans hit SEND... and it sent.
Checked the port setting and it was still 465.
Checked Yahoo and the message was there.

So... I will turn the Automatically Check for Messages back on and see if it still pops up that box asking for my User Name and Password... Give me a few minutes to make the changes and let it run... to see what happens.
Try changing the outgoing to 465.

It didn't like the 465 once I set up the 15 Automatic Check For Messages.
I turned off the Auto Check and tested Manually... and now that crapped out.
I changed Outgoing back to 25 and tested Manually... no joy.

Sooo... I set Outgoing and Incoming back to Default to see what would happen. Figured I couldn't break it any more than it was...

Manual test with 110 and 25 defaults worked...
Sent test messages from other email clients... received them manually just fine.
Turned Auto Check back on and tested manually... worked with no pop up.

Finally, I tested the Auto Check with two emails from other email clients and waited... right on schedule, the messages showed up. Not trusting it, I tested a second time and waited... and the sent messages showed up again.

I have no idea what the issues is/was... but, for now anyway, setting the ports to 110 and 25 defaults seems to be playing nice with the Outlook auto check feature. I have no idea where the 995 port setting came from... I have flashbacks of setting up the account and 110 jogs my memory... 995 not so much.

I will keep an eye on it for the near future and see if it continues to play nice with Auto Check... and will report back one way or the other.

There are so many nuances, features and tools inside Outlook... I need to get with someone to help me tweak it properly down the road. For now, I am back to running my business as "normal" and I thank you ever so much for your recommendations. It got me looking in the right place and finally got it to work!

All the best!
Try changing the outgoing to 465.
As a follow up...

I looked online for 995 vs 110 and see that 110 is for non-encrypted and 995 is for secure transmission.

So, I reset it back to 995 and left the outgoing to 25... no joy manually or automatically.
Switched back to 110 and 25... works fine.

Looked up 465 vs 25 on Outgoing.
Saw that 587 was recommended as well as 2525 and 25... 465 was not.
So, I tested 587 and it works. Tested 2525 and no joy... so Outgoing will only accept 25 and 587.
Incoming will only work with 110 now... so no secure Incoming with 995... period.

In the end, I have 110 and either 25 or 587 that will work manually and with Auto Check. I need to contact my ISP and ask what may have changed on their end as far as supporting 995. It would be nice to have the added security.

Thanks again!
Outgoing with SSL usually wants 465 or 587.
25 works sometimes but usually only without SSL
Choose File | Account Settings | Account Settings
Click the Change button. Click the More Settings button. Select the Security tab. Deselect the "Always prompt for logon credentials" check box

Hope this information helps you.
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