Microsoft Apps and the Mac

September 1st, 2008

Most of you know that Microsoft’s Mac Office apps all originated on the Mac in the 1980s, before they were duplicated on the then-fledgling Windows platform. Now before you remind me about that old political gaffe about being in favor of something before you were against it, that should, in theory, indicate that the world’s largest software developer ought to be able to build the best Mac products on the planet.

But that is not necessarily true.

Sure, Office for the Mac has a huge market share. That may be due, in large part, to the fact that people who switched from Windows want to work with what, to them at least, is the tried and the true, and not have to seek out a new set of productivity applications. In multi-platform environments, the system admins prefer to have equivalent software for their Mac and PC users. It sure lessens the learning curve, and enhances compatibility.

After occasional stumbles, it’s also true that Microsoft’s Mac Business Unit has tried hard to infuse the appropriate Mac-like interface elements into their software. If anything, Office for the Mac is probably superior to the Windows version, even thought the latter sports extra stuff.

Unfortunately, perhaps in the drive to provide comparable products, Office for the Mac suffers from the same useless complexities of the typical Windows product. We all know, for example, about the deep-seated menus in Word that offer functions few ever heard of or perhaps will ever need. One of the big selling points of Office 2001, the last Classic version, and Office 2008, the first Universal version, was discoverability. That means making the hidden features more accessible, so you can take advantage of the sheer power of these applications.

However, you sometimes wonder when enough is enough. Apple, in contrast, is perennially spare with its features, and only adds them over time, in a gradual fashion. In fact there are still some Classic Mac OS capabilities that have yet to find their way into Mac OS X. It may well be that they’ll never appear, or that Apple will simply find a different — hopefully better — way of doing things.

Unlike Microsoft, with its committee-based approach, Apple doesn’t appear to build software based on bullet points of features.

One blatant example of Microsoft’s overkill is Entourage 2008, which may be the least changed component of Office 2008. Now I’ve had a love/hate relationship with the program over the years. I like its auto-correct feature when writing email, but I then encounter one of its quirks, and, as the frustration grows, I return to Apple Mail.

In large part, Entourage is descended from Microsoft’s original Mac email application, Outlook Express. That, in turn, contained some of the concepts that originally appeared in Claris Emailer before that application was folded. Indeed, many of the members of the original Emailer programming team went to Microsoft to work on Outlook Express.

To be sure, if you take Outlook Express for the Mac and learn it fully, you’ll understand much of the layout of Entourage. Of course, you have to fold in the calendar and task management feature.

I returned to Entourage a few days ago, when I encountered some difficulties with IMAP email handling in Mail. I contacted the support team at HostGator to find out why I was getting such weird prompts as “You exceeded mail quota” when Mail tried to parse junk mail or when I attempted to move a message from one IMAP folder to another.

Before you ask, my actual email storage quota, which I can configure myself since we lease the entire Web server, is twice what we actually use. The problem that confounded HostGator’s admins was that the message was random, and not always repeated. They responded that they felt Entourage had superior IMAP handling, so I gave it a try. Alas, the error messages still appeared, but they were more obscure, such as “Unable to add message to IMAP mailbox.” Yes, that’s Microsoft for you.

As I navigated through Entourage’s IMAP account settings, I found several times as many as Apple offers, with little, if any, explanation as to what they did and why I’d use them. Indeed, when HostGator’s admins suggested some specific settings, I found that they were not necessarily the defaults, as opposed to Mail, where the proper settings are usually configured automatically if you use the Setup Assistant. Go figure.

Finally, the source of the email setting was traced to a problematic default quota configuration on the server, which was fixed using a function in the Web Host Manager configuration panel. I decided to stick with Entourage for a while to see if really represented a superior solution. Alas, I encountered another long-term problem with the application, the failure to update email messages despite the correct scheduling. In theory, it should check for new messages at the repeating interval you select. In practice, sometimes you have to click on the Inbox of an account for it to update. No amount of rejiggering preferences seems to eliminate the problem, which is random.

Since this Entourage quirk is something I have encountered with every single version, with different email servers, I decided to choose simplicity over needless complexity and unreliability. I’m back to Mail again, and I’m so glad I don’t need to access a MIcrosoft Exchange server, where I would not be able to consider such a move.

And, don’t get me started about the weird errors Keychain Access reports when you run Keychain First Aid after setting up Entourage.

| Print This Article Print This Article

13 Responses to “Microsoft Apps and the Mac”

  1. Andrew says:

    Goes to show the varied things we do with our computers and that what works for some, doesn’t for others.

    I like Apple Mail a lot, and would use it if I wasn’t on an Exchange server. Of course, just as Gene comments how he’s glad to not be on Exchange, I couldn’t imagine what I would do without it.

    I use Entourage 2008 on my MacBook, Entourage 2004 on my office manager’s MacBook, Outlook 2003 on my paralegal and receptionist’s PCs and Outlook 2007 on my MacBook in Boot Camp. All of our calendars are shared, and Exchange makes it easy, eliminating the need to synchronize anything. We have email distribution groups where I can choose who gets what, and I can also control who can access what on the calendar, and what level of control they have.

    Leopard server may do the same thing, I’m not sure as I needed (and bought) this solution in early 2006, but it works seamlessly and fast with Exchange.

  2. Arnold Ziffel says:

    I used Word 5.0 on our old MacSE, and it allowed me to recreate countless letters written by a WWII relative.

    Now, I don’t mess with Word unless I absolutely have to…like at work. All the “features” of Word drive me crazy

    when I’m trying to write. Is it bloatware? No, it’s blimpware!

  3. Byron says:

    When setting up schedules in Entourage (Tools>Schedules), be sure to click on the button which reads “Click here for account options”. This will bring up a detailed list of the folders on your IMAP server, and you can specify which ones Entourage is meant to update when it is running a schedule. I have had no problem with items not appearing in Entourage ever since I ticked the checkboxes next to the main folders I need to access constantly.

  4. As I said, everything is checked and accounted for. No difference.


  5. Chris Beshore says:

    I use entourage strictly for email connecting to Small Business Server 2003. While I had constant connection problems with Entourage 2004, the new 2008 Entourage connects fine. This “feature” in itself is worth it to me! As a side note, having used both, I think that Outlook 2007 for windows is far superior to Entourage 2008.

  6. AdamC says:

    Good choice….

  7. Joe says:

    I just wasted 15 minutes with that old nightmare – formatting in Word. I hate how you format something and earlier parts of the document change. You’d think after 20+ years they’d learn how to handle formatting.

    Fortunately, I was almost immediately reminded of how lucky I am. I purchased several new computers and Intuit Quickbooks Point of Sale. It wouldn’t run on the Vista computers. After 6 hours on the phone (uninstall this, change that, reboot, command line, blah, blah, blah) I did a google search and found the answer – reinstall Vista from the OEM disks (I’m not sure why that helped since it was a virgin installation, anyway, but it did).

    That reminded me how lucky I am using Macs even with the insane Microsoft formatting methods.

  8. Kirk says:

    I just switched to host gator I am getting constant messages from Apple Mail that I have exceeded my quota. My site’s disk quota is 10 times what my actual mailbox usage is. In your post you mentioned that you changed a default quota configuration to fix the problem. While I can change my own domain’s default, the server’s default doesn’t appear to be editable.

    How, or what specifically did you change? (if you can remember)

    Thanks in advance.

  9. Kirk wrote:

    I just switched to host gator I am getting constant messages from Apple Mail that I have exceeded my quota. My site’s disk quota is 10 times what my actual mailbox usage is. In your post you mentioned that you changed a default quota configuration to fix the problem. While I can change my own domain’s default, the server’s default doesn’t appear to be editable.

    How, or what specifically did you change? (if you can remember)

    Thanks in advance.

    OK, what is your mailbox setting? If you go over 2GB for a mailbox using the Courier IMAP email server software on your site, you might run into messages of this sort.


  10. Kirk says:

    Mailbo setting is currently 2GB. Current usage is 133mb. The weird thing is that I can quit mail then reopen and the message goes away. The other problem is when trying to move messages. I get an error that the message can’t be moved because disk quota exceeded. Yet I simply move the message again and it works. Strange. Hostgator people say Apple Mail is the problem, but I know it’s not.

  11. Actually, it may be a corrupted mailbox size file. They can fix that for you. Or just set it slightly below 2GB.

    If you have control of the WHM interface (and not just cPanel), which is true for a dedicated server, you can also switch email server software from Courier to Dovecot, which is less sensitive to such irritants. No, it’s not Apple Mail. Mail is just sensitive to the problem.


  12. Kirk says:


    Thanks for the help. I modified my mailbox quota and although it says change was successful, it also said “invalid maildirsize’ which to my mind represents a problem since I lowered the quota to an even 2000 MB (2GB).

    I will open a ticket with hostgator to look into it.

    Thanks very much for the help!

  13. @ Kirk: I’ve seen that. They will have to delete a file, called maildirsize, that will restore proper functionality, although the message itself is essentially bogus.

    It’s in the Mail folder for the account in question but it’s not something I expect you can access on a normal shared account.


Leave Your Comment