I have disable sleep on the Macs as well. This was happening in 10.8.5 as well, so I don't think its iCloud Keychain related. I have reset the keychain multiple times, made sure its the default and made sure it is not locked. The Exchange accounts will sometimes ask for password, but never show the port error in keychain repair. There are 5 mail accounts in total on the worst offender, 3 that connect to the Communigate server and 2 that are Exchange. It happens on the imap item and the smtp item. Running Verify Keychain will sometimes show that the keychain needs to be repaired and will show the mail accounts Item “” has unspecified value for port attribute. The problem email accounts are connecting to a mail server running Communigate ( not sure the exact version, but its likely 4 years old ) Microsoft Outlook for Mac is version 14.3.9 There is no ryhme or reason the behavior. Outlook is constantly asking for the passwords for these specific accounts. I manage multiple Macs and have found an error that I am unable to fix.
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