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This article was published on September 16, 2009

If there’s one thing Microsoft is better at than Apple, it’s… email.

If there’s one thing Microsoft is better at than Apple, it’s… email.
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Ralf Rottmann is a serial entrepreneur from Germany. He successfully sold his last business to Alcatel-Lucent. Follow him as @24z on Twitter Ralf Rottmann is a serial entrepreneur from Germany. He successfully sold his last business to Alcatel-Lucent. Follow him as @24z on Twitter and on Google+

AppleMailStuckBack when Apple announced first Snow Leopard, I got quite enthusiastic about the idea of getting rid of Microsoft Entourage 2008, Redmond’s “Outlook for Mac OS X”.

I even twittered about my personal #nomoreentourage day. While I am an absolute Apple fan boy with iMacs and MacBook Pros everywhere in our offices and a proud iPhone owner since the very beginning, I am sad to admit: Apple Mail 4.1 sucks big time.

This is not meant to be a 1:1 comparison of features. It’s not even a software review. There are many things with Entourage that at least leave room for improvement. But there are some issues with Snow Leopard’s Mail, that are an absolute no-go if you intend to use email professionally, or just beyond occasionally sending greetings to aunt Martha:

1. Sending attachments bigger than 3 MB via your Exchange account is pure luck

Yep, I’m serious. Apple Mail 4.1 has difficulties handling 3+ MB file attachments. Wanna send out a nice PDF of your latest presentation to your customer? Good luck! As usual there is no official statement from Apple regarding this issue, but you might want to take this quote from a recent discussion I’ve opened as Apple’s position on the issue:

I just got off the phone with Apple support about the same issue. They told me that Mail only sends up to 20MB. I don’t know how much I can/can’t send except my attachments that are 15-30MB won’t send out. I set up my Entourage account again and checked to see if I could send there and I could.

Apple support said they didn’t know if this would be fixed or not. I can’t believe that they wouldn’t fix this issue as most Exchange users are going to be working with big attachments etc.

One terrible side effect of the problem is, that mails that fail to get delivered block your entire outbox. So once a single email gets stuck in the queue, all subsequent emails will not be sent, either. If unread counts would work reliably, you’d be lucky to find out; unfortunately unread counts are quite unreliable in Apple Mail.

2. Inline attachment display

mailattachmentsiconizer_20071217171003This might be personal taste, but I simply hate how Apple Mail “expands” document attachments inline or places icons anywhere within the body of emails. The only way to stop this ugly behavior is to switch to plain text mode; which obviously also takes away any means to style your emails. This issue has been with Mail since its first iteration. I assume Apple is very well aware of it, or why do they actively advertise a plug-in written by Adam Nohejl, that lets users decide how attachments are handled?

As of this writing, the Snow Leopard version should be available in a few days.

3. The ugly, ugly Address Book

Microsoft’s Outlook and Entourage feature a tight integration between Calendar, Address Book and Email. Apple has spread these tasks up to three distinct applications. When I first switched from Entourage to Mail my intuition told me that these three belong together but I thought it might just be another case of “getting used to an Apple approach to a problem” which would ultimately turn out to be the better way.

Well, it didn’t.

iCal is quite okay, though it lacks many of the advanced views I fell in love with from my Entourage times. Apple’s Address Book application, though, is a nightmare. Keeping things simple in general is a good principle. However, reducing an essential tool as a contact manager down to adding, search and editing capabilities with absolutely no options for view customization, filtering, categorization etc. is simply failing big time. Apple’s Address Book application turned out to be totally useless for me.

4. Apple Mail launches fast but almost falls asleep when communicating with your Exchange server

Many complaints can be found regarding Entourage’s speed, or better, its failure to perform well. With Microsoft’s recent 12.2.0 Update, the launch time did improve slightly but it’s still below how fast Apple Mail fires up. But that’s almost the only area where Apple Mail wins. Getting mail, moving a bunch of emails to Exchange folders, handling calendar events and almost every other activity that requires communicating with Exchange takes longer with Apple Mail than with Microsoft’s app.

If you’re like me, you almost never quit an application. Consequently subsequent application performance per task is way more important than initial launch time. Again and sad to say: Entourage outperforms Mail big time.

Microsoft Outlook coming to a Mac near you

To make a long story short: I’ve switched back to Entourage 2008. All my colleagues did so, too. I still consider Exchange integration a key Snow Leopard feature and a reason for many to upgrade. If you’re using email professionally, be aware that Entourage will very likely stay around for a while.

Clearly, you get Apple Mail free while you’ve got to pay for getting Entourage with Exchange support. But free software that fails to deliver key requirements has no value, anyway.

Microsoft recently announced Outlook for Mac users. If Redmond is clever and puts the right price tag on the box, chances are Apple Exchange users never revisit Apple Mail, again.

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