Outlook disconnects regularly and I get the following error message

Anonymous
2012-06-10T10:00:07+00:00

The server for account "Yahoo" returned the error "[SERVERBUG] AUTHENTICATE Unable to open mailbox; please try again later." Your username/password or security settings may be incorrect. Would you like to try re-entering your password?

When I re-enter my password, I always tick the box to "remember the password in the keychain".

Then Outlook connects but disconnects after a while.

In general, the account is always disconnected after a long period of inactivity (say overnight).

Any tips?

Outlook | MacOS | Legacy Outlook for Mac | For business

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Anonymous
2012-06-11T21:42:23+00:00

I think the port setting are incorrect. Usually Incoming Port is 995. I would switch these instructions.

Another site suggested these setting that are a bit different. Why does this have to be so confusing? :-( 

Incoming mail server settings

POP server: pop3.mail.yahoo.com

Use SSL: Set this enabled.

Port: 995

Outgoing mail server (SMTP) settings

SMTP server: smtp.mail.yahoo.com

Use SSL: Enable SSL.

Port: Use 465 as the port.

Use authentication: Set this enabled.

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  2. Anonymous
    2012-06-11T21:31:33+00:00

    In Keychain Access, in the top right is a search box. Type in Yahoo. 

    I only found the “imap.mail.yahoo.com” listed for my account as well. Not sure why it doesn't have the other one.

    If you fail to get this fixed...

    Test in a new Identity. It's possible it's your current Identity. If this works,  I suggest you move to a new Identity. Follow directions here:

    How to move your data to a new Identity

    If this fails....

    Create a new User in System Preferences and test entering your Yahoo account in this clean environment. If it fails there, try entering as POP. By Default, Outlook will setup Yahoo as POP. You should be able to just enter your email address and password and let Outllook setup automatically.

    Here are the setting I found for Yahoo POP.

    Yahoo Incoming Mail Server (POP3) - pop.mail.yahoo.com (SSL enabled, port 465)

    Yahoo Outgoing Mail Server (SMTP) - smtp.mail.yahoo.com (SSL enabled, port 995)

    [See my next comment about ports.]

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  3. Anonymous
    2012-06-11T20:22:07+00:00

    Thank you. I did everything you suggested. 

    I run the Keychain First aid and sure enough it had errors. I repaired them and the set off to do the rest.

    However in the Keychain Access I cannot find the ougoing mail server. I can find the incoming one (imap.mail.yahoo.com) but not the outgoing one. 

    As a result, the account keeps disconnecting and then asking for the password again.

    When I key in the password, I go to the Keychain Access again and the errors are still there. The error I get is "Item “imap.mail.yahoo.com” is a duplicate; this item's port attribute is not set".

    I clear the error again and everything seems to be working correctly until the next time the same cycle of errors happens all over again....

    Really not sure what to do

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