
I have Mavericks and Outlook 2011. Every time my computer goes to sleep, it forgets the passwords it needs for my Gmail accounts in Outlook. It only happens when it sleeps. Otherwise I stay signed in just fine. Microsoft remote desktop connection client for mac 2.1 2.1.1. I get an error message that says something about 'invalid account or password.' I re-enter my password when prompted, and then it resumes working just fine. Why is Outlook forgetting my passwords?
5 days ago - Select the email message that you want to save in MSG format. Click the File tab. For Microsoft Outlook 2011/2016 on Mac: Select the.
(I do constantly check the 'remember my password in Keychain' checkbox; and I have checked my profiles to make sure the passwords are saved correctly in Outlook.) This is super-annoying. All, I found a solution that resolved Outlook from requesting you re-enter the password for the email accounts following a period when the computer is asleep. With Outlook open, use Finder to select the Applications folder, then the MSOffice folder, then holding the Control key down select the Outlook 'O' icon, and select 'Get Info' from the list. Within the Get Info screen presented, check the 'Prevent Nap App' box.
Then close Finder, close Oulook and then re-open Outlook and your problem will be solved. This action prevents the Outlook app from sleeping under Mavericks control which was designed to save power consumption, however Microsoft did not modify Outlook to conform to this feature so you must check and activate the 'Prevent App Nap'.
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. All, I found a solution that resolved Outlook from requesting you re-enter the password for the email accounts following a period when the computer is asleep. With Outlook open, use Finder to select the Applications folder, then the MSOffice folder, then holding the Control key down select the Outlook 'O' icon, and select 'Get Info' from the list. 
Within the Get Info screen presented, check the 'Prevent Nap App' box. Then close Finder, close Oulook and then re-open Outlook and your problem will be solved. This action prevents the Outlook app from sleeping under Mavericks control which was designed to save power consumption, however Microsoft did not modify Outlook to conform to this feature so you must check and activate the 'Prevent App Nap'. Eric no problem. 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. 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.