The Next Web

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

By Ralf Rottmann
September 16, 2009
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If theres one thing Microsoft is better at than Apple, its... email.Back 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

If theres one thing Microsoft is better at than Apple, its... email.This 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.


  • Oh no! Another Pro-Microsoft post on TheNextWeb today? What is happening???
  • We're simply living up to our unrivaled commitment of not being biased. :-)
  • The sky is falling! The world is ending! Wait... my MacBook's turning into a Windows PC as I type! Actually, some good points Ralf - I've always preferred Outlook to Mail, although I use neither; I stick to the Gmail web interface.
  • You are right, its not perfect. We use the gmail IMAP service which works fairly well. No problem with attachements. The lokiware plugin for handling attachements is not ready for Snow Leopard. That is a big problem indeed.
  • What's wrong with gmail (google apps version for own domain) in a safari browser and IMAP access via iPhone?
  • I totally agree. I'm in an Exchange environment with a mac. Entourage is definitely the lesser of two evils. The good integration between calender and mail (sending and recieving invitations for example) on Entourage just works. There are many things that it isn't good at (archiving and search for example), but Mail.app+iCal just seems broken on some very important issues.
  • Well yeah, but Entourage is just so… ugly.
  • Sebastian
    i so wish entourage was the lesser of 2 evil: after a few weeks it always stops to work for me entirely. it just does not sync with the server then anymore. Only a reinstall fixes that problem.
    So while Mail.app has lots of flaws it is so far more reliable then entourage...
    Speaking of flaws: i hate that i can not move my "sent email" from other accounts to the exchange account. No rules on sending emails? what the hell...
  • Where does Thunderbird fit into all of this? Great for emails (POP3, IMAP, GMail, Exchange (I think)), loads of settings for rules and accounts and a nifty calendar by way of 'Lightning'. Cross platform and easy to modify too.
  • pji
    Agreed. I'm not a big fan of Entourage but Thunderbird + Lightening is head and shoulders above anything else... If Outlook could handle imap worth a damn it would be the obvious choice. I'm curious to see if Outlook for Mac will be something different or Entourage by another name.
  • DAve Doyle
    Mail has it's shortcomings but talk to me when Outlook stops using Word to render HTML and leaps into the 21st century with it's CSS support.
  • Don
    I've been using Exchange in Apple Mail for a few weeks, and while it's sometimes a little quirky, the ability to search my email FAST and ACCURATELY has made my life after Entourage a delight!
  • Couldn't disagree more.

    I hated Apple Mail when I first started using it. Then I grew to quickly appreciate it. It's simpler and faster then Entourage. It works better then Outlook ever did for me.

    I used Entourage to connect to Exchange and switched to the web services version when it came out. It never worked well. It was slow, clunky and dragged the whole computer down. Mail works perfectly with Exchange. I haven't had a single issue with large attachments and I send 5-6 MB attachments on a regular basis.

    Address Book is the weakest link in the bunch but the organization is quite good. You can create static groups or smart groups. And, best of all, you can create custom fields on the cards. And not using the Address Book leaves you out of all of the contact list integration that weaves throughout Mac applications.

    And, finally, the biggest selling point for me is iCal's ability to support multiple Exchange servers. When you do consulting it's fantastic to be able to see a composite calendar of multiple Exchange systems.
  • thejay
    I've never encountered such problems despite having sent 100mb+ email attachments from Mail before. I've just tried sending a 35mb email attachment to myself (other email account) and sure enough it was sent without a hitch.

    I'm on snow leopard.
  • In which corporate environment is okay to send 30MB email attachments? At my employer (35,000 employees) you'd get a nasty call from the Exchange Server admin and told to use the file system. Plus, the company security policy limits the size of incorming and outgoing attachments to reduce the risk of malicious code spreading and data leakage.


    "When a message contains elements that are not plain US-ASCII text, the elements must be encoded. When dealing with such non-text content, including attachments, MIME is used for encoding. Both Exchange 2007 and earlier versions of Exchange Server use the Base64 algorithm to encode attachments. And the disadvantage of Base64 is that it bloats attachments by 33%." - http://technet.microsoft.com/en-us/magazine/200...

    Other than that I agree about the short comings in Mail and iCal.
  • When a message contains elements that are not plain US-ASCII text, the elements must be encoded. When dealing with such non-text content, including attachments, MIME is used for encoding. Both Exchange 2007 and earlier versions of Exchange Server use the Base64 algorithm to encode attachments. And the disadvantage of Base64 is that it bloats attachments by 33%.
  • Mortimer P
    http://www.itwriting.com/blog/1743-apple-snow-l...

    I also came here via HN, but I wanted to rail against this link bait, scream it down for the IT support nightmare that is Exchange and Entourage, but really, the link above cuts the emotion and speaks straight to the facts:
    both sides can debate over debate-able points like "better". What works in real-world experience and after users have 30GBs of mail, and filing bug reports and waiting for support, that's a valuable thing to discuss as well. Mr. Anderson is closer to a path I can benefit from following, and your readers may feel the same way.
  • Just to emphasize a point that has been made in the comments: Apple Mail works reasonably well with IMAP and POP3 accounts. My post is focussing specifically on the Exchange integration, which simply is a no-go if you're forced to use Exchange based email in a corporate environment.

    The key aspect is, that Apple actively states exactly the Exchange integration time and again as one of Snow Leopards biggest enhancements.

    It is not unless it works. And it doesn't.
  • Mushishi
    Also... not QQ-ing !
  • Arne
    For me the biggest problem using Apple Mail with an exchange server is that there is no option to use public folders, one of the key features of an exchange server. Hopefully they will integrate it soon. On the other hand side entourage is really looking awful and not using the best way to connect to an exchange server but it works ... So we can hope and pray for two things, first Apple Mail will be getting a few new features or Outlook for Mac will be so good ... :)
    Best, Arne
  • Destro
    @ cschep,

    You can use rules to only keep email (in Apple Mail) from a certain time period. I have rules set up to archive anything more than 6 months old, so my inbox (and the server space I occupy) stay reasonably clean.

    And this is on exchange, by the way. I almost completely disagree with the author here. Before Snow leopard, we were force to use Entourage for all things Exchange... which is "pretty," but not very pleasant to use. The coolest thing about it were it's project management features, which we didn't use because our department uses tools that perform that task much better that Entourage ever will. Besides that, it is slow, bloated, and unreliable; on many occasions I've had it stop syncing and unable to connect to the Exchange server, until it refused to work at all and I had to just give up on it and revert to accessing my Exchange mail via web browser. When it id work, search was piss-poor, I had to jump through hoops to remove emails that I didn't want added to my address book, and it would lag and stall at random for minutes at a time.

    Mail on Snow Leopard is all I need. I'm glad that mail, calendars, and the address book are split into separate apps. There is no reason to cram it all into one app and bloat it to no end. I regularly send email attachments (either multiple or one at a time) that weigh in at more than 10MB (though I probably shouldn't email files of that size), and have had no problems. I suggest you check with you IT administrator regarding your problems sending attachments. Like I mentioned to cschep, I have a slew of rules that handles mail from multiple accounts (so that I can view all of my inboxes together and tell their constituent emails apart from one another), rules that move certain emails to other locations based on specific criteria, and rules that handle spam that the filters don't catch, among other things. I also really appreciate the ability to view my email as threads.

    As far as email attachments showing up in random places in an email, all you have to do is go to Edit > Attachments and you can set the option to always insert attachments at the end of your messages. You can also set this on a per email basis.

    Syncing speed is not a problem here either. In the Mail preferences, you can set the interval at which you want Mail to check for email (anywhere between a minute or an hour, or manually). I have an iPhone that is connected to the same exchange server ((the iPhone uses push notifications to get Exchange mail), and typically when I get a mail notification on my iPhone, Mail gets the same email(s) seconds later at the most, if not simultaneously. It receives mail fast, and sends mail fast.

    iCal/Exchange calendar integration handles all of my needs. Meeting invitations reliably show up in both Mail and iCal, and I can accept/decline right from mail or iCal. I've had no problems here so far. One feature that I would like to see here is the ability to reserve conference rooms in a meeting invitation, which, oddly enough, Entourage can't do but Outlook does. I also agree with Arne about accessing public folders, which should be included.

    Someone else already addressed the Address Book topics. It is trivial to create groups (static or smart groups), add custom fields, and search your local address book database or the Exchange server (lightning fast, might I add) for any contact info. This functionality is extended to *any* application that ties in to the Address Book framework.

    There are definitely some features that Entourage/Outlook has that Mail could use, but it isn't missing anything that I absolutely need in order to make use of it. And what it does do, I have to say it blows Entourage out of the water. It is a much more usable, unobtrusive application.
  • Melissa
    I would suggest that you continue using Apple Mail and Addresses - it took me awhile to see the benefit too (b/c we are so use to the way Microsoft works), but when I lost power to my MacBook and lost all of my information in Entourage, I decided to give Apple Mail and Addresses another look - and it turns out that I do like it! The attachment issue, in my opinion, is a choice that Microsoft has made to not convert the attachment. If I send an email with photos attached to a friend who has an Apple, they receive attachments. Why doesn't a PC? Because Microsoft chooses not to display the photos as attachments. When I send photos to my PC family, I just direct them to my mobileme account and let them download the photos themselves. Then, there is no need to send photos via email. But, a great work-around to this problem is to compress the photos into a zip folder and send to PC users. It works great!

    Lovin my MacBook! (I never thought that I'd say those words - I thought it was all hype, but it is not; it is just what you are use to). When I purchases an airport extreme and set it up in less than 10 minutes; including printing wirelessly and streaming music wirelessly, I was even more sold! Yahhhhhooooo! I love it!

    WIChemEngr
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