If you use Microsoft Outlook 2011 for OS X, after upgrading to OS X Mavericks you might find the program periodically forgetting passwords for your various accounts, and continually prompting you to enter them.
This may happen when the computer wakes from sleep, or may happen after a period of inactivity, especially if you are using other programs and have not accessed Outlook in a while.
It appears in some systems, Outlook may suffer from some bugs with Apple’s new App Nap application-handling service in OS X Mavericks. This service is supposed to allow a program to be effectively stopped from executing when it is in the background, allowing for faster performance for foreground applications in addition to better battery life for laptop systems.
In the information window, expand the General section and then check the box for “Prevent App Nap.” This will keep the program more active in general, but might also improve its ability to maintain connections with your e-mail servers.
In addition to App Nap, you might have problems with the account keychain entries that Outlook uses to store your login credentials. If any keychain entry gets damaged, then it may not work properly with the program that created it. Therefore, you can try removing the keychain entries for your configured e-mail accounts, and have Outlook recreate them:
- Open the Keychain Access utility (in the Applications > Utilities folder)
- Select the “login” keychain
- Search for the e-mail service (ie, the server name) of the account you have configured in Outlook.
- Select the displayed keychain entry, and press the Delete key to remove it.
When finished, launch Outlook again, and when prompted, supply your password for the server. After doing this, a new keychain entry will be created to replace the one you deleted, and Outlook should now be able to access your servers again without prompting you to log in.
Apple Mail has had a problem for a long time forgetting account login information, long before Mavericks came on the scene. Indeed, the issue does not appear to be specific to any one version of Mail or of OS X. The solution I use is to go into the SMTP settings for my accounts and restore the passwords that Mail somehow deleted.
I find that removing the email account entries in the keychain is very successful at resolving Outlook password issues. Though the instructions say to launch Outlook after modifying the keychain, they didn’t explicitly say to Quit Outlook before going into the Keychain. So make sure you quit Outlook first, then modify the keychain and then LogOut or restart your Mac (I have seen OSX refuse to actually remove keychain entries unless you do one of those two things).
this does’t work!
I have found the problem, in July 2015 Google in its wisdom decided to automatically block email programs (including outlook) that it considered less secure than gmail. It therefore blocks and the clue is you start getting these emails:
Someone just tried to sign in to your Google Account “your email” from an app that doesn’t meet modern security standards.
Thursday, 3 September 2015 09:52 (Irish Standard Time)
We strongly recommend that you use a secure app, like Gmail, to access your account. All apps made by Google meet these security standards. Using a less secure app, on the other hand, could leave your account vulnerable. Learn more.
Google stopped this sign-in attempt, but you should review your recently used devices:
REVIEW YOUR DEVICES NOW
So to fix it follow the review devices link button and turn on the radio button to allow for basic access…. it should be mentioned Microsoft didn’t exactly shout about the solution as it highlights that their outlook is less secure than gmail 😉
Hope this helps folks