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Moving from Entourage to Apple Mail

Posted 8 years ago in Tech by Rod Drury
Posted by Rod Drury

Over the weekend we migrated to Exchange 2007 (actually its still going for some of our staff). The fact that you need to move and synchronize all your email is just nuts but that’s another story. The 58,000 emails in my inbox took about 20 hours to copy over. Maybe this year we’ll get an email archiving solution.

One of the things that made us want to move to Exchange 2007 is support for Apple Mail, Address Book and Calendar on the Snow Leopard Operating System. So I was very interested in seeing what it was like moving from Entourage (where Mail, Contacts Calendar are all together) to the separate application approach of Apple.

Entourage was OK, but with my massive mailbox (which emails should I delete?) it was getting very slow. Often I’d be waiting 10-20 seconds to get a response.  One of the problems is that Entourage uses one huge file to store everything.  This means you need to exclude it from your  Time Machine back up (which is fine because everything is on Exchange). If your Exchange file gets corrupted then you are in for a world of pain. Another reason is it is sluggish is that Entourage is not developed in Cocoa, the native Leopard development framework.

So with interest, as soon as the Exchange migration completed, I fired up  The setup was so easy. Basically you enter your email address and password and mail starts syncing across.

The feel of the applications, especially Mail, feels a bit simplistic but it does what you need to do.  There is no native 3 pane view but I found a 3rd party tool called Letterbox to get that.

But everything is so fast.  Searching is really easy and it just hums.  That is probably because stores everything in files and spotlight search is fully integrated.  iCal and Address Book seem to work well.  The snappiness is also clear when you just open your MacBook to get mail.  It seems ready to go immediately.

As Blackberries connect to Exchange, not the Mail client it works exactly as before.  We can now use ActiveSync to connect iPhones so we’ll do some speed tests on iPhone vs Blackberry connecting to Exchange.

While the minimal UI is currently attractive, the apps do feel light weight.  But with things like GMail, light mail feels better.  However I don’t understand why Apple doesn’t target business more and add some easy features to make it just a bit richer. A native 3 pane UI is an obvious omission.  A simple formatting toolbar would be nice.

Later this year we’ll see Outlook for the Mac.  Looking forward to testing that and to see if I can be lured back.

The bottom line is I like my Mac better without Entourage. It works well.


March 17, 2010 at 4.01 am

ah, I gave up on Entourage about 2 weeks into using it as I found it pathetic in performance too, so now I exclusively use mail, ical and address book for the just over a year, but I do still miss using Outlook. I’ll give Letterbox a try though.

Brendyn Montgomery
March 17, 2010 at 9.07 am

Probably not an option as you already have an exchange server but in a mac only environment Daylite by Marketcircle is a killer contact, calendaring and tasks management app with a free server component – integrates with apple mail and lets you make tasks from email etc. – It is extremely robust and we use it over the air with iphones etc. Just a thought

March 17, 2010 at 10.34 am

Did you consider Gmail?

Just figured it might have been a contender considering the pro-cloud nature of Xero.

Rod Drury Xero
March 17, 2010 at 10.44 am

@Matt. Yes we have looked at GMail. We have email integrated deeply into our back office systems and still prefer Exchange. We did move into a hosted exchange cluster so it is outsourced and off premise.

We do keep an eye on Gmail and other products to move to the cloud. I’d certainly like to see some more innovation especially on Google Docs. Seems to have stalled for the past year or so.


March 17, 2010 at 11.06 am

What were your reasons for not moving to Exchange 2010? The cross-browser OWA client would have appealed to you?

Paul Rushworth
March 17, 2010 at 11.38 am


As Rod indicated, we’ve moved to a Managed Exchange instance, and the availability of 2010 with this vendor (Revera) is around ~6 months off. We’re happy to wait at the moment.

2010 would have been an option, if we were prepared to self-host, (which is something we were considering initially) but we ruled this out.

Self-hosting exchange for a company of our size is easy- doing it properly is hard and expensive. (Primarily building a scalable platform that is sufficiently redundant).

The days of placing Edge, Hub & Mailbox on the same piece of physical hardware and hoping for the best are gone – This is why you’re seeing Microsoft pulling back on products like Essential Business Server.

March 17, 2010 at 12.14 pm

Paul, I know all about designing Exchange infrastructures (I do this for a living,) I only mentioned it because Rod’s comment made it sound as if you were setting up your own Exchange cluster, albeit hosted in someone else’s data centre. Did you not consider using Microsoft’s hosted Exchange? That wouldn’t have given you Exchange 2010 yet either, but they have good tools which allow deep integration into your directory.

Paul Rushworth
March 17, 2010 at 12.20 pm


There were a few (non-typical?) advantages of where we were, and where we moved to, over Microsoft’s own hosted product-. The biggest was probably having backups stored with in the same Commvault system, which gave us a slightly easier approach concerning data migration.

Revera’s system uses EMS-Cortex (NZ developed!) and allows AD integration.

John Younger
March 17, 2010 at 1.40 pm

Hi Rod;
Mate if you have 58,000 emails in your Inbox you might want to think about taking a couple days off to sort them out!
Now I know why you never replied to my last email…..

March 18, 2010 at 1.06 pm

We dumped Exchange for Google Apps about a year ago and we couldn’t be happier. @Rod – I agree with you about Google Docs being pretty poor so we don’t use it. But debating just email platform, my preference is Gmail (and it’s free!).

Gopal Patle
March 18, 2010 at 9.57 pm

I believe Microsoft recommend a 5000 item limit on mail folders for reliability?

Jason Blumer, CPA
March 29, 2010 at 2.32 pm

I may be moving our CPA firm over to Gmail Apps Premier this fall (from self-hosted Exchange). I’ll be investing in Microsoft Office for Mac 2011, and then I’ll synch with Gmail. If that works well, and we still have the usability of Outlook, I’ll move the other staff over at the beginning of 2011.

@Chris, drop me a line, I would love to know how your migration from Exchange to Google Apps went. email – jason [at] blumercpas [dot] com

Miki Szikszai
March 29, 2010 at 5.16 pm

Exchange 2007 and mail,ical and address book work very slickly. We had a couple of issues with people in our team where Entourage and ical fought with each other all the time – needed to remove Entourage completely including lots of permissions. Complete nightmare – that stuff sticks like a limpet…

You’ll notice you get better battery life on your mac on wireless now Rod – Entourage chews up a heap of cycles and the wifi wont be quite so busy either. My Mac Book was on about 2.5 hours with Entourage and runs close to 4 hours without it.

Rod Drury Xero
March 29, 2010 at 6.18 pm

Thanks Miki. My biggest existing problem is getting iCal invitations into the right (exchange) calendar. Still jazzed by the speed of mail.

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