I manage multiple Macs and have found an error that I am unable to fix. Outlook is constantly asking for the passwords for these specific accounts. There is no ryhme or reason the behavior.
- The Macs are running 10.9.1
- Microsoft Outlook for Mac is version 14.3.9
- The problem email accounts are connecting to a mail server running Communigate ( not sure the exact version, but its likely 4 years old )
- Running Verify Keychain will sometimes show that the keychain needs to be repaired and will show the mail accounts Item “mail.xxxxx.com” has unspecified value for port attribute. It happens on the imap item and the smtp item. The smtp port is non standard at 1200.
- There are 5 mail accounts in total on the worst offender, 3 that connect to the Communigate server and 2 that are Exchange.
- The Exchange accounts will sometimes ask for password, but never show the port error in keychain repair.
- I have reset the keychain multiple times, made sure its the default and made sure it is not locked.
- This was happening in 10.8.5 as well, so I don't think its iCloud Keychain related.
- I have disable sleep on the Macs as well.
I just also added a different users account that uses the same Communigate server to another MacBook Pro and it shows the same behavior.
I don't think its the Communigate server, if that wasn't working it would not work all the time.
I do believe it is something to do with how the passwords are stored in the Keychain.