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Exchange Mail Issues after Lion Upgrade

Is anyone else experiencing major issues with your Exchange email account(s) in Mail after upgrading to Lion?

Posted on Jul 21, 2011 9:27 PM

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132 replies

Jul 22, 2011 12:29 AM in response to blkcrdmbr

Yes. Unable to connect to Exchange 2007 server using Mac Mail after upgrading to Lion. I have tried deleting the SSL certificate from the Exchange server & reimporting then set to Always Trust. Still unable to connect Mail, iCal or Address Book to the Exchange account. Unable to find much on the problem yet so hopefully a resolutions comes out.

Jul 22, 2011 9:37 AM in response to blkcrdmbr

Yes, I am as well.


I sync with three Excahnge accounts on two seperate computers (both MBP running Lion). On both computers, one of my Exchange accounts refuses to display the Inbox messages. I've tried deleting and readding the account many times. I even configured it as an Exchange IMAP connection, but the same issue cropped up.

Jul 26, 2011 6:21 AM in response to joshbennett

I'm having serious problems with Exchange and Mac Mail since upgrading to Lion. All my POP accounts work fine. Our machines that are still on Snow Leopard still work fine. But the machines on Lion can get the list of email items (Onbox, Sent, Drafts etc) but when you click on a mail, the Preview Window just says "Loading" indefinitely. If you double click, the windows that opens does the same - it simply displays "Loading".


This does not happen with every mail, just some - and the ones it happes with, it happens with every time. No amount of closing and re-opening the Mail app, or selecting a different mailbox and then reselecting the Exchange one will solve it.


Was excited when I saw this fix... but what you explain is just not how things are in our Exchange Server. We're running Exchange from SBS 2008, and EWS is not under 'Default Website' in IIS Manager, it is under 'SBS Web Apps'. When I click on it, I do not get an Authentication option.


Does anyone have an idea how to apply the above fix to Exchange?


Thanks in advance of anything you can suggest.

Jul 26, 2011 7:26 AM in response to DoctorDee

I have just tested a standard configuration of SBS 2008 running Exchange 2007 with Lion, the above fix does not apply to SBS 2008 exchange deployments as the EWS is already configured for basic authenticationby default.



Lion requires attest Exchange Service Pack 1 with update Rollup4 or later.


Next steps:


Backup your system


Install Exchange 2007 Service Pack 3 available here http://technet.microsoft.com/en-us/exchange/bb330843.aspx.

Jul 26, 2011 8:52 AM in response to joshbennett

While researching your fix I discovered that doing this disables encrypted passwords so all passwords for your exchange server are sent clear tex. If you're sending via wireless then a packet sniffer can easily pick up these passwords. This is a HUGE security hole for your exchange server. I hope your exchange admin knows what he's doing by disabling that.


This isn't going to be a problem if you're using SSL or HTTPS connections.


There has to be another solution other than to send passwords in clear text.

Jul 26, 2011 1:31 PM in response to blkcrdmbr

I spent over two hours yesterday trying to get my exchange accounts added after Lion upgrade; either through mail, ical, or system settings, it crashed anything I tried.


Got this fix today, and it worked flawlessly; I'm now accessing all of my mail, contacts, and calendar items in Mail and iCal. Not sure if this varies based on serverside setup, but it's easy to try.


It seems that the latest Mac OS X Lion (10.7) shipped with a bug in the certificate checking. While we don't have a software fix from Apple at this point, we do have a way to fix the issue.


Here are the steps:


1.In Finder, open your Utilities folder and double-click Keychain Access

2.Once Keychain Access loads, in the menubar, click "Keychain Access" -> "Preferences"

3.In the Preferences window, click "Certificates"

4.Change the dropdown for "Online Certificate Status Protocol (OCSP):" to "Off"

5.Change the dropdown for "Certificate Revocation List (CRL):" to "Off"

6.Close the Preferences window

7.Quit Keychain Access

8.And you're done!

Jul 28, 2011 5:18 PM in response to aroszak

Can confirm that Aroszak's solution does NOT work while inside my corporate network. I think we're on Exchange server 1941...or 2003. We haven't been able to reliably use Entourage or Mac Mail for years inside. Will have to try at home. Not sure I'm going to have any luck though, but we'll see.


Haven't loaded entourage 2008, but will also try that next.

Jul 28, 2011 11:43 PM in response to blkcrdmbr

I and a few other people in another post who may also be on Exchange are having a problem of folders not showing up. I've deleted my Exchange account in Mail and added it in again and it syncs and everything is there. Then folders stop appearing and if I wait or close and open mail and wait, they may come back. Is this one of the problems you are having?


All the folders are there and I can access them fine with Outlook in Win7 and on iOS devices. So it's just Lion Mail that is having the problem.

Exchange Mail Issues after Lion Upgrade

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