So i do this and then tick the box to save password to key chain and press enter and this saves the imap password and i then check and go to account preferences in outlook to make sure this has been saved and its there i do this with all imap accounts every couple of hours P The issue is with Microsoft Outlook 2011 with all imap accounts (i have multiplie imap accounts) not saving the password in keychain well it does for while say for an hour or so then the dialogue box pops up in outlook and asks you to enter the account password for that email account. I have both a Macbook Pro 13" 2011 model & 27" iMac 2013 Model and both are running Maverick 10.9.1 & with Microsoft Office 14.9.3. I do believe it is something to do with how the passwords are stored in the Keychain. I don't think its the Communigate server, if that wasn't working it would not work all the time. 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 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.
Have you already added your Gmail account to Outlook then see, Improved authentication for existing Gmail users. This is for users who are on Build 0902 and higher. If you are adding Gmail, you will get a prompt within Outlook to sign-in to your Google account.If adding a Yahoo, or other IMAP or POP account, you might be taken to those sites and asked to allow Outlook to access your mail, contacts, and calendars.(Your screen might look different from this one depending on the account you’re adding.) Click the plus ( +) sign > New Account.
Select Outlook > Preferences > Account.Most email accounts, including Office 365, Exchange server accounts,, , and Google accounts can be set up in a few quick steps.
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