Constant prompts for credentials from one Mac Outlook 2011 client

Question

The majority of my Exchange users are all on Windows 7 and have no issues (at least using Outlook...) but a subset of the executives are ardent Mac users running Outlook 2011 for OS X. One of these clients is prompted every 5-10 minutes for credentials. Ticking the checkbox to remember credentials does not fix the situation.

Mac version is 10.7.2.

I have already removed and rebuilt the EWS virtual directory on my Client Access server.

Outlook anywhere is set to NTLM authentication.

None of the Microsoft clients are experiencing this issue.

What else can I do to make this issue go away?

Solution 1

There may be something off in the way the user's password is being stored in their keychain. Run the Keychain Access utility (from the user's account). If the keychain list isn't shown in the sidebar, choose View menu > Show Keychains. Select the "login" keychain in the sidebar, then run some checks:

1. Open Keychain First Aid (under the Keychain Access menu), enter the user's account password, select Repair, and click Start. If it finds (& repairs) any problems, check to see if that's solved the problem.
2. With the login keychain still selected, choose Edit menu > Change Settings for Keychain "login". In the settings dialog, check the autolock settings for the keychain; if it's set to lock after, say, 5 minutes, and Outlook checks for incoming messages every 10 minutes, the keychain will lock between each check. Generally, you want its autolock time to be longer than the email checkin time. (Note: if Outlook caches the password rather than rechecking the password each time, this will not be an issue; I haven't used it, so I don't know.)
3. If neither of those does the trick, try deleting the relevant keychain entry (/entries), and having Outlook recreate them (with the remember credentials option). Note that starting in OS X 10.9, there's a second user keychain (called either Local Items or iCloud), and you may need to delete entries both there & in the login keychain. It's possible there's something wrong with the entry, or its access policy, or there are multiple conflicting entries; deleting & recreating the entry is generally the simplest way to fix this.

Solution 2

Try to add an additional backslash ("\") in front of your logon domain.

Try to use:

\domain\username

instead of

domain\username

This triggers a bug (feature) in the MacOS keychain, which leads to persistent credentials.

Comments

[Admin]

There is a Microsoft article that will solve this issue: support.microsoft.com/en-gb/help/4010106/…

[Top__Hat]

Before rebuilding the keychain the user deleted the client profile and tried to start again fresh, but the problem was still occurring. The above fix resolved the issue and it has been three days now since the last popup. Thank you!

[AWippler]

I have also seen this in the wild as well. When the user is prompted for a password in Outlook 2011, it means the password field in Preferences -> accounts is blank. One may also fix this problem by ensuring the password is there in the password field.

[Ben L.]

Is there any more information about this "feature"?

[Joe Carroll]

This covers the specific Keychain items in more detail: answers.microsoft.com/en-us/msoffice/forum/…

[Thomas]

Just an FYI, this is not a forum but a Question and Answer site. Comments such as this should usually be kept to the comments on a question or moved to the chat room for more in depth discussion. That way people looking for answers can find them more easily.