My New MacBook Pro and Exchange

If you’ve been following along at home, you know that I just got a new MacBook Pro and am going to give it a shot for a while due to my current frustration with my laptop and all things Vista.  My partner Chris suggested to me that it’s not about productivity or frustration; rather it’s my endless desire to play with electronic toys (he is likely correct, but I need a business rationalization for my behavior.)

My biggest historical barrier to using a Mac has been our deep reliance on Exchange.  I’m a very heavy Outlook / Exchange users and exercise it fully (yes – I use tasks.)  All of my previous experiences – either with Entourage 2004 or my feeble attempts to get all the “pieces” working (e.g. mail, calendar, contacts, and tasks) on Mac apps with an Exchange data store have been failures.

I know that I have a default option of using Outlook in a Vista window on the Mac running Parallels or VMWare Fusion (I’ll try them both.)  But that doesn’t really feel very satisfying to me.  I just got a copy of Entourage 2008 Beta so I’ll give that a try and a good workout, although early reports are that Task Sync is still not implemented.

Are there any other real alternatives out there in the world, short of dumping Exchange (which is not going to happen)?  Help me Obi-Mac-A-Roni.  And – thanks to everyone (all 34 of you) that commented on the previous Mac post.  Ross assures me that he is installing every last piece of software that y’all recommended.

  • Mark

    Virtualized Outlook is the only option; there is nothing available for the Macintosh to fully leverage an Exchange server, and there is nothing available that does everything an Exchange server does. I'm a Macintosh consultant and have been looking for this solution for months, it's just not there (and OS X 10.5 Server isn't it either.) Old habits die hard, good luck with your Mac.

  • James Cham

    I agree with Mark. With Parallels, you can run Outlook as if it was running as a Mac OSX application. I have been doing this for the last few months at home and it is the best of both worlds so far. (Full disclosure: Parallels is a portfolio company of the firm I work at but I would say the same thing one way or the other.)

  • Andre

    If Entourage 2008 doesn't have task sync then I'll have to believe that Microsoft is being feeble on purpose to annoy their customers.. For task management from my Mac, I went with http://www.rememberthemilk.com (RTM) which, while it's a parallel data store separate from Exchange, is absolutely fantastic and ever improving. It has a great, flexible Web client for managing tasks in multiple categories, the ability to assign tasks to other RTM users, offline access using Google Gears, an iPhone interface, automatic over-the-air sync to a Windows Mobile 5/6 client and much more. If your goal is the same as mine which is online/offline access to tasks grouped into categories, it's fantastic. Also, it's free! Going for the Pro option is just $25/year. I've been using it every day for months and highly recommend it. The developers are on fire!

  • Brian Hart

    I spent the better part of a day trying Exchange with the built-in Mail app and with Thunderbird, and neither worked with our Exchange server. Error messages were of the “General Error!” variety, too, so troubleshooting was difficult. I finally settled on Entourage 2004 for one reason: the reminder popups that Fusion/Outlook2007 gave me weren't obvious enough and I was afraid of missing meetings. Otherwise, it'd be Fusion/Outlook2007 all the way.

    IMO the lack of decent Exchange support for OSX would be a huge hurdle for companies looking to adopt Mac into their environments. Of course, that means there's probably an opportunity for some software firm to come up with something…

  • http://falseprecision.typepad.com/my_weblog/ Todd Vernon

    I just can't go here again. This is the single biggest reason I can never switch to the mac – and Microsoft knows it. If it works send up a flare :-)

  • http://alankeister.wordpress.com Alan Keister

    I have an external monitor for Windows in Parallels. It works really well. I have OS X on the laptop screen and Windows full screen on the external monitor. It seems like two computers that share a mouse and keyboard. It is the only solution I have found that works well. We use exchange and blackberries heavily at work. Entourage is just terrible.

    MS Office apps such as Word, Excel, Powerpoint work much better in Windows than Mac. So the dual screen approach helps with that as well.

  • Bruce

    Parallels and Fusion play along so nicely with os x, that Outlook will literally be just another open window on your desktop. If it's what you know and love, you should keep using it, the experience is seamless. If your workflow with Exchange and Outlook is good and you've geared yourself that way, don't change.

    That being said, if you want to use mac native stuff to replace the functionality of outlook, you can get there. The most important bit will be using Snerdware products – http://www.snerdware.com/ - Groupcal and AddressX. In the most recent versions of Groupcal, they seem to have finally gotten things working as they should. I used to have some problems with things dropping in place where they should, especially if a meeting request originated with someone else, but I haven't seem that same level of problem in the latest rev. So, using those will put you in the position of using a troika of : mail app of your choice, iCal, and Address Book.

  • http://learntoduck.com micah

    a couple things: http://www.macintouch.com/leopard/compat.html is a list of apps that have had trouble in Leopard. VMWare is faster than Parallels due it its ability to take advantage of both processors. GroupCal (http://www.snerdware.com/groupcal/) does a great job of syncing, except leopard broke it, and its not supposed to be fixed until 2008Q1. I use entourage with sync services on (to ical and .mac), and then use spanning sync ( http://www.spanningsync.com) to add in google calendar.

    I dont use tasks much (you've met me, do I look like I work?) so I cant help you there, except that Apple Mail has a nice task integration.

    Post about your experiences with Entourage 2008!

    Another newer cooler feature is Back to My Mac, which is like GoToMyPC, but integrated into the os and .mac.

  • http://philswenson.com phil swenson

    I'm curious about this topic. With GMail for domains available (for free), why are companies so bound to Exchange (esp small companies, large companies can never change anything – so I get that). What is it about Exchange that is so compelling? Is it the message history? Is it Outlook? All the sync plugins?

    Everywhere I work the companies are tied to Exchange and no one can keep the thing running properly. Outlook crashes, Exchange is down all the time, message boxes are always full, etc.

    I just don't get it.

    • http://www.feld.com Brad Feld

      It's called “switching costs.” Google is making it easier by the day to consider seriously.

      • Brian Hart

        There's something warm & fuzzy about having the email reside on an internal server instead of at Google… even though Google is less likely to hose your mail database than your internal server or mail folks.

        Not that I subscribe to that thinking personally, but I understand why some would have it.

    • JimR

      Security would be one reason to host it on your own internal server. Who knows what Google is going to do with your email. Also, some businesses fall under certain laws for keeping back-ups, which you could not rely on Google for.

      Also, does Google have functionality like Blackberry Enterprise Server (to use Blackberries) or the capability to use other smart devices that Excahnge offers? At our small company, everyone has either a BB or a Motorola Q, which the server syncs everything to.

  • gards

    I have had the same dilemma and Parallels with Outlook is not an option. Entourage 08' may be your only choice for full Exchange integration. If you can replace your exchange server, Zimbra – http://www.zimbra.com has a native Mac client and from what I see trumps exchange. Unfortunately, the Mac client doesn't have IMAP support yet, so you need to be running the Zimbra mail server. Let us know our thoughts on Entourage '08.

  • Jeff Clavier

    I have been using both a PC and a Mac for 3 years now, with pretty much the same environment. I use Entourage on my Mac, and I am happy with the Exchange integration expect for the lack of Todo list support. And I have been using ChronoSync to replicate my files hosted on my Windows 2000 Domain on the Mac.

    You know where to find me if you need more info :-).

  • http://infusion.vox.com/ Ben Gertzfield

    I'm a bit biased (full disclosure: I'm lead developer on VMware Fusion), but I find running Outlook in a Fusion VM is really the only way to go.

    Entourage for Mac, even the new 2008 beta, still can't book resources for meetings (it can only invite people). This is pretty much a non-starter for me, as I need to book meeting rooms all the time.

  • http://www.rassoc.com/gregr/weblog Greg Reinacker

    Brad, I just use the built-in Leopard mail app. The only thing it doesn't do well is calendar integration – but I've finally worked out a system to keep my calendar in sync, and it's only slightly less convenient than Outlook was.

  • Mark

    Virtualized Outlook is the only option; there is nothing available for the Macintosh to fully leverage an Exchange server, and there is nothing available that does everything an Exchange server does. I'm a Macintosh consultant and have been looking for this solution for months, it's just not there (and OS X 10.5 Server isn't it either.) Old habits die hard, good luck with your Mac.

  • Andre

    If Entourage 2008 doesn't have task sync then I'll have to believe that Microsoft is being feeble on purpose to annoy their customers.. For task management from my Mac, I went with http://www.rememberthemilk.com (RTM) which, while it's a parallel data store separate from Exchange, is absolutely fantastic and ever improving. It has a great, flexible Web client for managing tasks in multiple categories, the ability to assign tasks to other RTM users, offline access using Google Gears, an iPhone interface, automatic over-the-air sync to a Windows Mobile 5/6 client and much more. If your goal is the same as mine which is online/offline access to tasks grouped into categories, it's fantastic. Also, it's free! Going for the Pro option is just $25/year. I've been using it every day for months and highly recommend it. The developers are on fire!

  • http://intensedebate.com/people/brian_hart1973 brian_hart1973

    I spent the better part of a day trying Exchange with the built-in Mail app and with Thunderbird, and neither worked with our Exchange server. Error messages were of the "General Error!" variety, too, so troubleshooting was difficult. I finally settled on Entourage 2004 for one reason: the reminder popups that Fusion/Outlook2007 gave me weren't obvious enough and I was afraid of missing meetings. Otherwise, it'd be Fusion/Outlook2007 all the way.

    IMO the lack of decent Exchange support for OSX would be a huge hurdle for companies looking to adopt Mac into their environments. Of course, that means there's probably an opportunity for some software firm to come up with something…

  • http://intensedebate.com/people/james_cham2382 james_cham2382

    I agree with Mark. With Parallels, you can run Outlook as if it was running as a Mac OSX application. I have been doing this for the last few months at home and it is the best of both worlds so far. (Full disclosure: Parallels is a portfolio company of the firm I work at but I would say the same thing one way or the other.)

  • http://intensedebate.com/people/todd_vernon84 todd_vernon84

    I just can't go here again. This is the single biggest reason I can never switch to the mac – and Microsoft knows it. If it works send up a flare :-)

  • Alan Keister

    I have an external monitor for Windows in Parallels. It works really well. I have OS X on the laptop screen and Windows full screen on the external monitor. It seems like two computers that share a mouse and keyboard. It is the only solution I have found that works well. We use exchange and blackberries heavily at work. Entourage is just terrible.

    MS Office apps such as Word, Excel, Powerpoint work much better in Windows than Mac. So the dual screen approach helps with that as well.

  • http://intensedebate.com/people/greg_reinac2315 greg_reinac2315

    Brad, I just use the built-in Leopard mail app. The only thing it doesn't do well is calendar integration – but I've finally worked out a system to keep my calendar in sync, and it's only slightly less convenient than Outlook was.

  • phil swenson

    I'm curious about this topic. With GMail for domains available (for free), why are companies so bound to Exchange (esp small companies, large companies can never change anything – so I get that). What is it about Exchange that is so compelling? Is it the message history? Is it Outlook? All the sync plugins?

    Everywhere I work the companies are tied to Exchange and no one can keep the thing running properly. Outlook crashes, Exchange is down all the time, message boxes are always full, etc.

    I just don't get it.

  • http://intensedebate.com/people/bruce2096 bruce2096

    Parallels and Fusion play along so nicely with os x, that Outlook will literally be just another open window on your desktop. If it's what you know and love, you should keep using it, the experience is seamless. If your workflow with Exchange and Outlook is good and you've geared yourself that way, don't change.

    That being said, if you want to use mac native stuff to replace the functionality of outlook, you can get there. The most important bit will be using Snerdware products – http://www.snerdware.com/ - Groupcal and AddressX. In the most recent versions of Groupcal, they seem to have finally gotten things working as they should. I used to have some problems with things dropping in place where they should, especially if a meeting request originated with someone else, but I haven't seem that same level of problem in the latest rev. So, using those will put you in the position of using a troika of : mail app of your choice, iCal, and Address Book.

  • Ben Gertzfield

    I'm a bit biased (full disclosure: I'm lead developer on VMware Fusion), but I find running Outlook in a Fusion VM is really the only way to go.

    Entourage for Mac, even the new 2008 beta, still can't book resources for meetings (it can only invite people). This is pretty much a non-starter for me, as I need to book meeting rooms all the time.

  • http://intensedebate.com/people/bfeld bfeld

    It's called "switching costs." Google is making it easier by the day to consider seriously.

  • gards

    I have had the same dilemma and Parallels with Outlook is not an option. Entourage 08' may be your only choice for full Exchange integration. If you can replace your exchange server, Zimbra – http://www.zimbra.com has a native Mac client and from what I see trumps exchange. Unfortunately, the Mac client doesn't have IMAP support yet, so you need to be running the Zimbra mail server. Let us know our thoughts on Entourage '08.

  • http://intensedebate.com/people/jeff_clavie2398 jeff_clavie2398

    I have been using both a PC and a Mac for 3 years now, with pretty much the same environment. I use Entourage on my Mac, and I am happy with the Exchange integration expect for the lack of Todo list support. And I have been using ChronoSync to replicate my files hosted on my Windows 2000 Domain on the Mac.

    You know where to find me if you need more info :-).

  • http://intensedebate.com/people/micah105 micah105

    a couple things: http://www.macintouch.com/leopard/compat.html is a list of apps that have had trouble in Leopard. VMWare is faster than Parallels due it its ability to take advantage of both processors. GroupCal (http://www.snerdware.com/groupcal/) does a great job of syncing, except leopard broke it, and its not supposed to be fixed until 2008Q1. I use entourage with sync services on (to ical and .mac), and then use spanning sync (http://www.spanningsync.com) to add in google calendar.

    I dont use tasks much (you've met me, do I look like I work?) so I cant help you there, except that Apple Mail has a nice task integration.

    Post about your experiences with Entourage 2008!

    Another newer cooler feature is Back to My Mac, which is like GoToMyPC, but integrated into the os and .mac.

  • http://intensedebate.com/people/brian_hart1973 brian_hart1973

    There's something warm & fuzzy about having the email reside on an internal server instead of at Google… even though Google is less likely to hose your mail database than your internal server or mail folks.

    Not that I subscribe to that thinking personally, but I understand why some would have it.

  • JimR

    Security would be one reason to host it on your own internal server. Who knows what Google is going to do with your email. Also, some businesses fall under certain laws for keeping back-ups, which you could not rely on Google for.

    Also, does Google have functionality like Blackberry Enterprise Server (to use Blackberries) or the capability to use other smart devices that Excahnge offers? At our small company, everyone has either a BB or a Motorola Q, which the server syncs everything to.

  • Reza

    Hi! I am using the iPhone 3G some while now it it works perfect with the sync to our corporate exchange server for syncing mail, calendar & contacts, no need for tasks which is apparently no option for the iPhone. Given the great experience on iPhone I changed to a new MacBook. Although Outlook under Parallels combination works fine, I would prefer using genuine Apple products – Mail, iCal and Address Book. Any attempt in setting up Mail with more or less the same inputs as I did on the iPhone didn't work. I'm not a Mac expert but would have thought if Exchange connection works on iPhone it should do so on MacBooc as well? Anyone any idea? Cheers

    • http://intensedebate.com/people/bfeld Brad Feld

      I don’t have the answer as I’ve switched back to running a PC with Vista.