Hands-On Report: Apple Mail 4.4 M$ Exchange Password Rejection--Fix [Updated 1-7-11]

by Bill Fox, MacsOnly.com January 4, 2011 [Updated January 7]

Ever since I installed the Mac OS X 10.6.5 update an old Snow Leopard Apple Mail issue has re-surfaced, i.e. an email server rejecting the provided password from Apple Mail during an automatic check for new email (see this article). With Mac OS X 10.6-10.6.1, it happened with all my POP accounts but not with my Exchange account--I had another problem with the Exchange account. With Mac OS X 10.6.5, rejecting my password has started happening with my Microsoft Exchange account. So what is causing this and how can it be stopped?


This very annoying issue has these symptoms: Mail pops a dialog box that states the Exchange server has rejected my password and provides a field to enter the "correct" one. However, if I do or even if I click cancel instead, the dialog box pops up again and again for a half dozen times or more before Mail finally takes the account offline. If I check every few minutes to see if I can take the account back online without the issue, after somewhere between 10-15 minutes the problem mysteriously clears up until it happens again in an hour or so. And during the 10-15 minutes it takes to clear, I am unable to login to my Exchange account with any Mac using Mail, Outlook 2011 or even directly on the Internet with any web browser.

The issue appeared to happen only with my Mac Pro, not with my MacBook Pro or Air or iPhone 4. I rarely have any of them other than my Mac Pro on all day with Apple Mail and iCal open with constant re-checks of the Exchange 2007 server for new email or calendar updates. So I am led, at least preliminarily, to conclude that it is probably not a systemic issue with Mac OS X 10.6.5 and Exchange.

Fix Attempts

The first things I tried was quitting and re-launching mail followed by restarting my Mac Pro--no joy unless, of course, doing so took longer that 10-15 minutes.

Searching Apple's Support Discussions turned up only a few suggestions. Some claimed there is an issue with iCal and Mail in syncing with Exchange in 10.6.5 that is fixed by re-installing the Mac OS X 10.6.5 combo updater. I did this and it appeared to reduce the frequency of the issue but alas it still happened.

In case the problem really is syncing, I stopped leaving iCal open all the time. This is inconvenient but so far the issue has not reoccurred in several days. This is not really a fix but a temporary workaround if, indeed, the issue does not re-occur.

Finally, I ran the verify routine of Keychain First Aid (KFA), something I actually should have done first. KFA is available in the Keychain Access application's pull down menu (first one under the application's name). KFA found a number of problems with port settings for my POP accounts and duplicate POP account entries so I ran the repair routine to fix them.

While KFA found no problems with my Exchange account, I looked closer at my Keychain entries for Exchange because of the duplication finds for my POP accounts and noticed that my Exchange account also had eight entries in my Keychain, four as Exchange and four more as the Exchange server's domain name. I could understand maybe having up to three or sets of three, one each for Mail, iCal and Outlook 2011 but not sets of four. Clicking on each Exchange entry and entering my administrator's password to see the Exchange password revealed that all but one of them had an expired password. Passwords for my Exchange account must be changed every 90 days but the seven expired passwords in these four sets of entries were not just serially the previous passwords.

I was tempted to delete the seven Keychain entries with the wrong password but instead I simply changed the password in each to the current correct one since I wasn't certain that deleting the extra entries that were not deemed as duplicates by KFA would not cause additional problems.

In Summary

There may be an inherent syncing conflict between Mail and iCal in Mac OS X 10.6.5 since the issue did not re-occur at least for a short time after leaving iCal unopened except to change or consult it. However, it may also be a problem with Snow Leopard's handling of Keychain password entries for Mail Exchange accounts that I manually fixed. Or maybe both?

I am going to leave iCal open for the next week to see if the password issue with Apple Mail's Exchange account re-occurs. If so, then the issue is probably caused by a syncing problem with iCal. If not, then it is likely that the issue was caused by the Keychain entry problems. I will report the results in an update.


After manually correcting (updating) the passwords for all of the Keychain's Exchange server entries on 1/3/11, I have not had any recurrences of the issue, even with iCal open simultaneously. Apparently, the outdated Exchange server entries were the problem. I updated to Mac OS X 10.6.6 on 1/6/11 and still have no recurrences of the issue.

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