Entourage Must Die

Okay, let’s be honest. I’m a Mac guy. I love Apple products, Apple software, and the Apple way of life. I make no excuses about that. That said, we’ve just go to deal with the gigantic pile of suck named Entourage.

If you don’t know, Entourage is essentially the Mac version of Microsoft Outlook. It comes with the Mac version of Office, along with Word and Excel. For some reason, Microsoft chose not to simply port Outlook over to OS X, much like they’ve done with the other Office programs. Instead, they started over and did their best to totally deconstruct a wonderful PC program, Outlook, and turn it into a useless, buggy, unreliable monstrosity named Entourage. What garbage.

For the past year and a half, I’ve been stuck on Entourage at work because our Exchange server won’t sync my calendar with any other Mac program. That also means I’ve been depending on Entourage for my email. There’s the problem.

Without going into the laundry list of problems, let me just focus on the main one: Entourage doesn’t want me to send some messages. At least once a week, as I’m typing an email, the entire message window closes. Poof. It just disappears. The message doesn’t get sent, it isn’t saved as a draft, it isn’t moved anywhere; it’s just gone. Forever.

What’s worse, it always, ALWAYS happens when I’m in the middle of a long, important, sensitive, and carefully crafted message, often addressed to my boss or other leaders of my company. When it happened yesterday, I threw in the towel. Entourage must die.

I’m locked into it for my calendar, but I have email options. I tried both Apple Mail and Mozilla Thunderbird throughout the day and decided on Mail. It’s nice and clean, super fast, and simple. By simple, I don’t mean weak; I just mean that it does one thing, and it apparently does it very well. I like that in an app. Entourage, on the other hand, chose to go the other direction. It does a thousand different things, and does them all poorly.

Apple Mail is not without its problems. There are some extremely elementary things that it should do, but doesn’t.  For example, the preview pane is at the bottom, with no option to move it to the side. Really? I’m sorry, is it 1996? Am I using this program on a 15″ CRT monitor? No. I’m using it on a dual monitor setup based on a 20″ widescreen iMac. I’ve got enough screen real estate. Let me put the preview pane on the right side like every other modern email program, won’t you? At least I solved this one with a third-party add-on, WideMail. This awesome plugin also allowed me to set my inbox message list exactly like I had it on Entourage (which I liked). See the side-by-side below.

Apple Mail vs. Entourage Message List

Apple Mail vs. Entourage Message List

Also annoying is the way it handles image and PDF attachments. Attachment isn’t even the right word, since you can’t really “attach” image files. Instead, Mail inserts the images inline in the message body, regardless of size, orientation, or anything else. Worse, it does the same thing with PDF documents. I’m sorry, I’m not a four-year-old-girl trying to figure out how to email a picture to my grandmommy. I’m a professional who has to email image files and PDF docs to other professionals, and sometimes to automated systems that don’t recognize embedded PDFs. Epic fail. Again, fixed with a third-party application.

And last, the most annoying of all is the one that, I must admit, is most characteristic of Apple. If you’re using the preview pane, there is no way under the sun to prevent Mail from marking a message as “read” if you’ve clicked on it. How ridiculous. Even I have to admit that choosing to not do the simplest thing, despite the fact that every other email program on earth does it, is a total Apple move. This one is killing me. Even if I sneak a peek at a message in the preview pane, I still like to keep messages marked as unread in the message list if I want to come back to them later. Having them all appear as read is a joke.

So, there’s my email rant of the year. Entourage stinks, Thunderbird failed out of the gate, and Apple Mail is workable, but comes up short on the most basic things. I hate to admit it, but finding a quality email client is the one part of the Apple lifestyle that I find hard to defend to the naysayers. It just makes me glad I use Gmail for my personal stuff.

UDPATE: There’s a possible fix for this random deleting behavior. Check the comments for this post.


10 Responses to Entourage Must Die

  1. I’ve been trying to figure out how this has happened. I did a search through our bug database and couldn’t find anything in any release that looked like this. I’ve run it by a few developers and testers, and no-one could come up with anything either.

    So I’m wondering if it’s possible that, in the course of your typing, you’ve managed to hit cmd-delete. When you do that, it’s an instant and full delete (not even in the trash). I know that I hit shift-delete all the time to delete the previous word, and I’m a touch-typist, so it’s not too hard for me to imagine accidentally hitting the command key instead of the shift key. The first time that you hit cmd-delete, you get a dialog asking if you’re really sure about that, and there’s a checkbox to never show this dialog again. So if you had hit cmd-delete intentionally in the past, and then clicked that checkbox to never see that dialog again, then it’s possible that this is what’s happening here.

    You could test this theory by going into the Entourage preferences, selecting Notifications, and then clicking the “reset confirmation dialogs” button.

    I understand if you don’t want to try again. If you do give it a go, I’d love to know the outcome.

    • Allen says:

      Okay, A+ for effort on this, Nadyne. I really appreciate you following up with this.

      I can’t say it’s impossible that I’ve never hit cmd-delete, but it is extremely unlikely. I never use shift-delete, so I can’t imagine anyway I could have accidentally hit a key command whose keys are that far apart. Plus, there’s no way I would have approved any dialogue box warning me of the immediate delete.

      Hey, since I have your attention, let me ask this: I applied the new Mac: Office security update this morning, and now a dialogue box pops up every two seconds asking if Entourage can access Keychain. I say “Always Allow” and it goes away. For two minutes. Then it’s back. Any thoughts or other reports on this?

      I’m going to stick with Apple Mail for a while, but it has it’s own challenges. 🙂

  2. Kurt says:

    I restarted my iMAC the last time this happened on an Office 2008 update and the keychain access problem went away. I wrote it off to a Windows product problem.

  3. Peter says:

    So no cure for this. How brutal Open a draft hit the delete button to edit it…and it’s gone. 10 hours of work. THanks Microsoft. I’ll get right on WIndows 7. And there weren’t no command delete synergies happening. I tested it with old drafts. It’s gone. UGHH

    • Allen says:

      Actually, there is a possible cure. There’s a VITAL check box that is deeply hidden in the prefs for Entourage. In Entourage, go to Preferences. Select Notifications in the left sidebar. Make sure that there is a check mark next to “Require confirmation when deleting.”

      When I first stumbled across this, it was not checked. Surely that can’t be the default, right? Anyway, if it is checked, Entourage will ask you before throwing your hard work out the window. You can test it by opening a new email message, typing in some gibberish, and then hitting cmd+delete. If you get a confirmation box, you should be relatively safe.

  4. Gillian says:

    So I’m trying to work out why Entourage must die if you’re still using it and you’ve stated that Mail is awful? You just feel bad because Entourage is actually better, but you can’t say it.

    I understand, i’m using Mail still against my better judgement, because surely the Apple program is better? I am suspecting that actually Entourage IS better and a quick trip with Google has confirmed my suspicions. Think I shall change back.

    (bring on the paperclip to properly attach things!!!)

    • Allen says:

      I do like having an all-in-one solution as opposed to a mix of iCal and Apple Mail. However, I wish there was a better solution than Entourage. I scream, “I HATE ENTOURAGE” at least three times a week.

      And to answer your question, I’m only still using Entourage because it’s my work machine, my company is on an Exchange server, and I have one of only a handful of Macs in the building. They can get Apple Mail working, but Address Book and iCal will not work with the Exchange server. I know Snow Leopard enabled Exchange support, but only for Exchange 2007, and my company is still on Exchange 2003.

  5. amy says:

    I’m an ambivalent Mac newbie after 25 years on a PC. I’m missing Outlook terribly and am struggling to make Mail work. May I ask what third-party app you use to “fix” the attachment annoyance in Mail?

  6. Tony Tiger says:

    Finally, a Mail client for the Mac that doesn’t suck.
    Have tested Outlook for Mac 2011 beta and at least it doesn’t strip tables from HTML. i.e. you can now paste Excel into emails. Also the image inline issues also look much better.

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