Outlook 2011 mac keeps asking for password exchange

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It happens on the imap item and the smtp item.

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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.

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I manage multiple Macs and have found an error that I am unable to fix.