Accessing Exchange from Mac OS X

Sadly, in a Windows centric environment, such as an Exchange organization, the Macs often get left behind. The Macs can play nicely with the PCs in terms of collaboration, but we can probably never expect them to have all the same features that Outlook and Exchange are capable of achieving.

On a Mac there are really only two options for accessing your Exchange mailbox, and that is an IMAP client or an OWA (Outlook Web Access) based client. Thankfully for us, most Apple computers already have both of these; Apple Mail and Microsoft Entourage. Both of these clients can interface with Exchange both over OWA or IMAP.

Apple Mail is the email client of choice for most Mac users, but its not the most ideal for an Exchange environment. Apple Mail includes the Exchange protocol as a choice when setting up a new account, but it is a hybrid of sorts. The Exchange protocol in Apple Mail uses IMAP to access the mailboxes and then it uses OWA to access the public folders. This works decently with Exchange 2003, but unfortunately support for Exchange 2007 is completely broken (and as far as I have been able to test is completely broken in Mail.app 3.0 included with 10.5). At least with Exchange 2003 the email function works, but many users have reported problems when working with large mailboxes (2GB+) and when working with public folders. Mail.app has a tendency to corrupt its message database when it is working with large folders and then the mailbox has to be rebuilt. Rebuilding the mailboxes is a very easy procedure, but it is still an unnecessary waste of a few minutes while you have to wait for the database to piece itself back together from the .emlx message store.

Next we have the issue of using Exchange’s collaborative features with Apple Mail. Exchange allows users to share address lists and resources/events through calendars. Apple’s programs for dealing with calendars and address lists are iCal and Address Book respectively. Apple’s sync services can synchronize with the user’s address list from Address Book on an hourly interval to save changes back to the server. This is not the greatest solution because if a users is only logging in for short periods of time their information may not always be synced back to the server. Apple’s Address Book application also allows for the Global Address List (GAL) to be accessed as an LDAP directory.

Accessing Exchange calendars through iCal is possible using a third party program called Groupcal by Snerdware. Snerdware’s Groupcal is supposed to be able to map Exchange categories to different iCal calendars and synchronize at a user specified interval. I purchased and tried using Groupcal with Exchange 2003, and ultimately became frustrated with the mistakes that it made, such as duplicates and recurring event errors. Also, Groupcal struggled while I was editing other users’ shared Exchange calendars.

Ultimately, I recommend users stay away from using the Apple messaging/collaboration products in an Exchange environment due to the complexity of configuration and broken support for Exchange 2007 with IMAP and Exchange protocols in Mail.app.

Here enters our second contender for Microsoft Exchange connectivity on a Mac, Microsoft Entourage 2004. Entourage 2004 by no means offers perfect Exchange support, but at the moment it is the best solution that I have tested for Apple computers. Entourage 2004 offers access to all of the primary Exchange features such as:

  1. Mail via OWA
  2. Read/unread & follow-up message flags
  3. Public Folders
  4. Personal Contacts
  5. Shared Contacts
  6. GAL via LDAP
  7. Personal Calendar
  8. Shared Calendars
  9. Public Calendars

And what it does not support:

  1. MAPI (RPC over HTTPS)
  2. Server-side categories
  3. Server-side rules
  4. Message reply flags
  5. Free/Busy scheduling – Updating attendee status
  6. Shared resource scheduling

Here are some Mac extras that Entourage 2004 has to offer:

  1. Spotlight indexing/searching
  2. Sync Services (iSync support for mobile devices and Synchronization with iCal and Address Book)

Most basic Exchange users will have no idea that they are missing any features that their Outlook counterparts have access too. The differences between Outlook and Entourage are even less noticeable when a user only uses a single computer. It is likely that Entourage 2008 will fill in many of the voids of Entourage 2004, with features such as server-side search, message reply flags, server-side categories, server-side rules, and free/busy scheduling (when paired with Exchange 2007). If you are trying to decide which platform to put your Mac organization on, it at least makes sense to go with Entourage 2004 knowing that it will be an easy upgrade to Entourage 2008 later this year.

As a side note, I run Parallels on my Mac in coherence and use Outlook 2007 as my mail client with Entourage 2004 configured just for the purpose of mailto: links. I intend on asking the Parallels team if they can at some point make some code so that Outlook can grab the Mac mailto: links.

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21 thoughts on “Accessing Exchange from Mac OS X”

  1. “It is likely that Entourage 2008 will fill in many of the voids of Entourage 2004, with features such as server-side search, message reply flags, server-side categories, server-side rules, and free/busy scheduling (when paired with Exchange 2007).”

    Our organization just updated to Exchange Server 2000. I realize that’s just a bit behind the times, but our Mac dept will take what we can get. After many years, we can now set appointments and receive meetings.

    The question is, when Entourage 2008 comes out… you mention its compatibility with Exchange 2007, for the features: server-side search, message-reply flags, server-side categories/rules, and free/busy scheduling. Will these features be available with Entourage 2008, running Exchange Server 2000? (We already have access to free/busy scheduling with Ent 2004/Exchange Server 2000-just no updating of attendee status) Also, any word about whether or not Entourage 2008 will support task items and shared resources?

    Thanks,
    Mims

  2. No, it is likely that many of those features will not work with Exchange 2000. This is because of the way that Microsoft has updated OWA 2007. If OWA 2000 doesn’t support a certain feature then there will be no way for Entourage 2008 to support it since Entourage uses OWA for interfacing with the Exchange server.

    The good news though is that at least you are finally off of Exchange 5.5. Exchange 2000 at least has a future for working in a Mac environment. I’m curious though why your organization moved to Exchange 2000 instead of 2003 though?

  3. I am not sure of the reasoning behind going only as far as Exchange 2000. A number of us would like to see them move to Exchange 2003. Perhaps they will be able to move more quickly to 2003 now.

  4. It would make the most sense to wait until Windows Server 2007 is released in September along with SP1 for Exchange Server 2007. Exchange 2007 is better in every way, IMO, than it’s predecessors unless you have to support some legacy clients; Outlook 2003 and 2002(XP), and Entourage 2004/2002(X) will work well with Ex2007, but 2001, 2000, 98, 97, and >95 are completely unsupported and likely will not work at all.

    That being said, unsupported by Microsoft often means that they just don’t want to be responsible for the tech support calls any longer, that they would like to sell their new product, or they just want to sell you a newer version (and rightfully so; if you are running Office 2000/97 it was time to upgrade a long time ago). If you are curious about any of the clients above, I have licenses for all of them but no longer have the media for anything older than 2002 (I do have 2000 though). If you can get me the install media, I would be happy to test and make a blog post about my findings.

  5. It’s now March 2008.
    Leopard is out and revised.

    Any hope for the current Apple Mail to play well with the current Exchange 2007? If so, exactly what patches do I need to insist my Exchange maven applies to make this work?

  6. I think that there is probably more hope now than ever of Apple Mail playing well with Exchange 2007 since Apple is adopting Exchange as their primary supported mail platform for the iPhone with Exchange Active Sync support. If Apple has already licensed the Exchange ActiveSync protocol then it wouldn’t be too much of a stretch for them to now integrate this into their iApps like Mail, iCal, and Address Book. Apple may be saying to just use Entourage though and I don’t see any reason why you shouldn’t just use Entourage 2008 if you have an Exchange 2007 account.

  7. Nice article, however I’d just like to make the point that if we lived in a mac world, where they ruled the business side of computing they would be locking windows out in the same kinds of ways.

  8. Update: Exchange 2007 is officially supported by Mail.app in OS X 10.6. About time. Exchange server 2003, unfortunately, is not supported – that’s because 2003 uses the Microsoft-proprietary MAPI protocol.

  9. It’s now June 2010. First my compliments for your blog.

    I am running Office 2011 beta 3 version, trying to connect to an exchange 2003 server. Unfortunately no luck so far. It seems that Exchange 2007 is needed. I have two questions.

    1. Am I correct that office 2011 does not work with exchange earlier than version 2007? If not, what am i doing wrong :-(.
    2. If so, do you know if this is a temporary problem that will be solved when the official version is released?

  10. @Sander thanks for the compliment.

    1. Office:mac 2011 does not work with pre-2007 Exchange so that means that 2003, 2000, etc. wont work.
    2. No, it won’t be fixed because this is the direction that Microsoft’s Mac BU went with Office 2008 when they released Entourage 13/EWS for 2008.

  11. Excellent Blog! I have Exchange 2007 and Outlook 2011 Mac Beta – I can get the account to connect (Green Light) on account setup page, but thats it! No mail, no contacts, no calendar. Can you help?

  12. How typical of Microsoft if you have the version of Entourage that came with the Home & Student version you cannot use it to access Exchange I.e you have to spend several hundred pounds to get the “normal” version.

  13. Hey.
    Is there a way to work on Mac (Snow Leopard 10.6.5) on the Windows Exchange 2000 Server? Probably not, if so, can I access an email by POP or any other way, excluding web interface?

  14. So, what is the answer when trying to connect Mac to Exchange 2003? It works seamlessly with the iphone and ipad, yet, i can now see it will not work with my new Mac..

    please advise.

  15. I am now using Outlook 2011 for Mac and various flavours of Entourage for years now. I think some of the confusion with Exchange compatiblity arises due to the number of different HTTP protocols that Exchange 2003/2007 has supported over the years: Exchange 2003 did RPC over HTTPS and little-known WebDAV. Exchange 2007 SP1 supports RPC over HTTP encapsulation, WebDAV and the latest Exchange Web Services. Entourage 2004/2008 used WebDAV. Outlook 2011 dropped WebDAV for Exchange Web Services which is only available to Exchange 2007 SP1 and later. WebDAV and EWS protocols have the upside that they allow Entourage/Outlook 2011 to connect to multiple Exchange Servers at the same time – something Outlook for PC usrs have been unable to do until Outlook 2010 which, guess what? also uses EWS protocol. Anthony Maw, B.Sc.,MCSE, Vancouver, Canada, 604-318-9994, anthony@maw.bc.ca

  16. Hi there,
    My client is running SBS 2003 on backend with several Mac runing Macmail. Most connect to Exchange with IMAP, but the owner is running Entourage 2008 which connects fine to Exch on the LAN, but he must make a VPN connection when away from office.
    I want to configure Outlook over RPC but must make sure it will work before I make any promises and start spending hours on the backend configuration.
    Does anyone know if it will work?

    Thanks!

  17. We did find a good workaround to this, but it depends on what your dependencies are as to whether it will work for you and whether the ‘approach’ fits for you.

    I moved to MAC just under two weeks ago after my Dell laptop died. We have SBS 2003 Exchange Server. Exchange works perfectly with the PC apps from Outlook 2003 through to 2010. I have been through a vertical learning curve understanding that with Office 2011 for MAC, it will not work with Exchange 2003. The 2011 Office for MAC is fantastic. However, I have had to abandon it because:

    1. We are migrating away from SBS Exchange 2003 to Gmail, so there is no point investing in an upgrade of Exchange 2007/2010 to make it MAC compatible.

    2. No matter what we tried, we couldn’t get calendar access into Outlook, synchronisation of tasks etc. although we could get access to emails via IMAP using Apple Mail (and MAC Outlook 2011) using the Dav ‘add-on’.

    What have I done to get around the problem? Heresy to MAC lovers I’m afraid. The MAC 2011 (Trial) has been uninstalled of my beloved Macbook Air. I’ve installed ‘Parallels’ v.7 and the PC version of Office 2010, including Outlook 2010. Works like a dream and synchronises perfectly with SBS Exchange 2003. I and my team have access to each others calendars, tasks and so forth.

    It’s a compromise, but at least I can stay on the Mac until we move to Gmail/Google Apps/Calendar when I hope that I will be able to move to native Mac once again.

    Best wishes.

    1. The real problem with running Parallels constantly to run Office 2010 is that its going to have some really negative affects on battery life.

      As far as migrating to Google Apps: I’d suggest really looking into what you’re missing out on by moving to Gmail from Exchange. Make sure to run a pilot program and at the very least, compare it with a migration to Office 365. There have been many businesses before you that have moved to Google Apps and realized it was a mistake (only to then realize that it is either too late/expensive to switch to something else, should have gone to Microsoft’s cloud platform for continuity of features, or should have upgraded internally for stability).

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