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Microsoft Entourage vs. Apple Mail (or Apple Mail vs. Microsoft Entourage)

October 12, 2009

November 2010 Update: Because I was so frustrated with the limitations of Apple Mail, I wrote this informative article for Mac|LIfe Magazine called 10 Ways to Soup Up Apple Mail.

January 2012 Update: Robin Benson keeps a great repository of Apple Mail plug-ins here.


It continues to boggle my mind that it is the year 2009, we’re up to Mac OS X 10.6 Snow Leopard, yet Apple STILL doesn’t understand how an email program should work. Apple simply doesn’t “get” email like other companies do, most notably Microsoft. (And believe me, I hate patting Microsoft on the back for anything.)

I sometimes wonder if the Apple executives even send emails at all, or if they are all too busy sending messages via brainwaves — which is no doubt a top-secret project that Apple must be working on.

More likely, it just gives even more proof to my ongoing theory that the people who work at Apple love resting on their laurels and rarely make important improvements to their software products after version 1.0, except for improvements that help their marketing department push software sales. Take a look at Apple’s iCal, Address Book, and the Finder — these products are almost identical to how they were years ago when they were first released. And take a look at a program like Apple Backup which we enjoyed using for online backups to our iDisk — Apple just silently discontinued this product without even giving anybody any warning about it. And the old version of Apple Backup does not work properly under 10.6 Snow Leopard because it no longer remembers its schedule for automated backups, so the product is dead at this point. And the iPhone — which is up to version 3.1 — still retains hundreds of bugs and problems that were present in version 1.0 (I will be talking about this in my next blog posting).

But out of all of Apple’s apps which have seen zero improvements, Mail is the worst offender of them all.

Every time I try to switch away from Microsoft Entourage to Apple Mail, I come running back even faster to Microsoft Entourage. Here are just some of the ways in which Apple doesn’t “get” email.

Below is a very short, incomplete list of Apple Mail vs. Microsoft Entourage, or “Why Apple Mail still sucks, even in Mac OS X 10.6“:

  • Rules don’t apply to messages that you’ve already read on other devices! WTF? Rules are super-important when it comes to email. If you’re like me, you live by your rules. However, Mail is extremely finicky about WHEN it will decide to actually apply rules to your incoming messages or not. If you’ve already read an email on another device (such as your iPhone), then Mail will NOT apply ANY incoming rules to that message when it shows up in your inbox later. Every other email program on the planet that I know of — including Entourage and Outlook — ALWAYS applies rules to messages that appear in your inbox, whether or not you’ve read those messages on other devices.
  • “Send Later” button — I have no idea why Apple hasn’t implemented a “send later” button along with a real outbox like Entourage, so you can queue your messages and send them later. This is a critical feature for people who use email professionally.
  • Editing subject names of incoming messages: This is probably the biggest limitation of Apple Mail. This is possible in Entourage and many other email clients, but not in Apple Mail. If you want to file away a message from someone and the title is “Re: Re: FW: Re: FW: Vacation”, you can change the subject to “Miami – July 2009 Trip” in Entourage, but not in Apple Mail. I like to file away all of my receipts and software serial #’s that I receive via email. But a lot of times the subject is something like “Your Order #12345 Has Been Processed” or something like that. In Entourage, you can change the subject line to whatever you want, such as: “OmniOutliner Serial Number”. (Note that this is accomplished via an AppleScript in Entourage 2008.)
  • If you have an IMAP email account, Mail doesn’t let you “unsubscribe” from individual folders on the IMAP server. You have to stare at ALL of your IMAP folders cluttering up your screen at all times, whether you want to see them or not, and whether you use them or not. Entourage — and all other email clients — let you subscribe or unsubscribe to any folders on the IMAP server that you so desire. So, for example, if you use a Google-based email account in Apple Mail, you are forced to stare at the “All Mail”, “Starred Mail”, and “Spam” folders — whether you use them or not. And you’ll always be looking at your IMAP “Drafts” folder too, even if you decide to store your Drafts locally in your local “Drafts” folder instead. Entourage also has about 25 other IMAP preferences to let you fine-tune your IMAP experience that Apple Mail doesn’t have. (Note: Gmail lets you control which IMAP folders will show up in Apple Mail, but other email hosting companies may not allow you to do this. In Gmail, go to your settings, and then go to the “Labs” tab. Enable “Advanced IMAP Controls”. Then go to the “Labels” tab and uncheck the box to “Show in IMAP” for any folders that you don’t want to appear.)
  • Apple Mail creates an extra folder on your IMAP server that you often cannot delete (depending on your IMAP server) entitled “Deleted Items”, even though your IMAP server already has its own deleted items folder, typically called “Trash”.
  • Entourage has super-robust scheduling that Apple Mail can’t even touch. You can schedule Entourage to check emails at certain times, or at ANY interval that you specify… and specify different schedules for different email accounts, if you like. You can delete messages from ANY folder within ANY time frame (not just 1 day, 1 week, 1 month, or never) at ANY point. And not just deleting messages, either. Just about every single command/function in all of Entourage can be scheduled to take place at any time that you specify.
  • Entourage has an incredibly comprehensive library of thousands of misspelled words for its auto-correct feature. (This is the same feature that is in Microsoft Word as well.) Meanwhile, Apple has NEVER had an auto-correct feature for Mail, and just recently in Snow Leopard introduced an auto-correct (text substitution) feature in its new “language and text” system preference. The problem, however, is that Apple has only given us ONE misspelled word in its library: substituting “the” for “teh”. Thanks for nothing, Apple. Meanwhile, Entourage can catch just about every common misspelling and adjust it automatically for you. Without a similar, comprehensive, pre-configured list from Apple in Snow Leopard, this text substitution feature is basically useless, and makes Microsoft’s software more attractive than Apple’s own software! (Update: TidBITS has generously released an autocorrect library for use in Snow Leopard.)
  • Outgoing rules: Entourage can automatically file outgoing messages or do other things to your outgoing messages AFTER they’re sent. Apple Mail cannot. Apple Mail only has INCOMING rules, not OUTGOING rules. (You need to purchase the Mail Act-On plug-in, which adds this functionality.)
  • Entourage has a notification alert window that pops up — no matter what app you’re using — to let you know what emails have just arrived. Mail doesn’t have this feature. You’ll need to add it with the GrowlMail plug-in.
  • If you check your email from an IMAP server that supports the IMAP IDLE command, you can get real-time “push email” of your emails directly to Entourage or Apple Mail. However, Apple Mail does NOT make an audio alert sound to notify you when you receive new push email in your inbox. Mail only makes an audio alert when you PULL email into your inbox (either by clicking on the “Get Mail” icon at the top of the screen, or by using Mail’s built-in scheduler). So, this completely defeats the purpose of having PUSH EMAIL to begin with, if you’re not going to be notified of your push email! A workaround to this is to install the GrowlMail plug-in, which gives you an optional audio alert whenever you receive ANY new email — regardless of whether it’s push email or pull email. If you want Growl to use the exact same “New Mail Sound” that Mail uses, you’ll need to make a copy of the “New Mail.aiff” file from Apple Mail (right-click on Apple Mail in the Finder, choose “Show Package Contents”, then open the Resources folder), and place a copy of that “New Mail.aiff” file into your ~/Library/Sounds folder.
  • Apple Mail doesn’t let you tag or file emails into colored categories (must be added via the Mail Tags plug-in), nor does it let you manually change the text color of incoming messages. You can manually change the background color, but not manually change the text color. (This can only be added with the Mail Act-On plug-in.)
  • Mail doesn’t let you put the preview pane on the right. (You must install the WideMail plug-in or the Letterbox plug-in to add this functionality.)
  • Threads of email messages: Entourage lets you click through the ENTIRE history of an ENTIRE thread of email messages, no matter where the messages have been filed away. Mail only lets you see the threads if they’re sitting within the same folder with each other.
  • In Entourage, any incoming or outgoing email message can be automatically assigned the color that you’ve assigned to that contact, because Entourage lets you color code contacts and then it applies those colors automatically as those messages come in (or go out, with an AppleScript). You can’t color-code ANY contacts in Apple’s Address Book, so any automatic color coding in Apple Mail has to be painstakingly done with rules and Address Book Groups (or the Mail Act-On plug-in.)
  • Mailing list manager: If you subscribe to lots of Internet mailing lists like I do, Entourage has an entire system that manages mailing lists in depth, including default options like “Reply Only To Sender, Instead of Entire List”. I couldn’t live without this functionality!
  • When attaching attachments in Entourage, you have the CHOICE of attaching the attachments as EMBEDDED in the body of the email itself OR just as an icon that doesn’t take up the entire body of your email. In Mail, you are forced to make ALL attachments embedded in the body, unless you right-click on each attachment and choose “View as Icon”, or use a plug-in such as the Mail Attachments iconizer plug-in. You can also use a program like Tinkertool to force Mail to embed all attachments as icons.
  • Entourage has built-in “text cleanup” options that let you highlight text and then increase quoting, decrease quoting, remove quoting, rewrap improperly-wrapped paragraphs, and change text to uppercase/lowercase. Apple Mail has finally started adding these features in 10.6, but they still don’t compare to Entourage. (The WordService service from Devon Technologies can help quite a bit with this.)
  • When deleting an old unused email account from Entourage, it DOESN’T go through your entire email program like a serial killer and delete all of your email messages that are sitting in your inbox/outbox/sent/trash. Entourage LEAVES your old messages behind for you to read later, but still lets you delete your email account. In Mail, if you delete an old email account, Mail CRAZILY deletes all of your old email as well (from the inbox/outbox/sent/trash) — even email that you may have wanted to read!! Mail is insane!! It actually DELETES emails, potentially against your will.
  • Entourage’s integrated Notes application is much more robust than the laughable Notes feature of Apple Mail. Don’t get me started on Apple Mail’s Notes feature — it simply isn’t usable or well-designed or really a finished feature yet. At least it finally started syncing with the iPhone in iPhone OS 3.0.
  • More on coloring: You can select any message at any time in Entourage, and quickly assign it a predefined color from the “Categories” toolbar menu without having to go through the clunky (and manual) color wheel selection process in Apple Mail. Furthermore, the color you assign in Entourage is visible from BOTH the list view and the message detail view of any message… not just the list view like in Mail.
  • In Entourage, any email message can be assigned to any number of categories and/or projects that you have setup, which give you the quick ability to search for, file away, and sort those messages later. These things simply aren’t possible in Mail, because categories and projects don’t exist in Mail. But, as mentioned above, the Mail Tags plug-in can help.
  • Entourage’s “advanced search” feature is much more robust than any sort of searches that you can do in Apple Mail, giving you many more choices than Apple Mail provides for creating a custom search. Apple Mail only has the bare minimum of searching capabilities. You’ll need to install the Rocketbox plug-in to bring Mail searching up to a more advanced level.

This is by no means an exhaustive list of the deficiencies in Apple Mail. This is just a brief list off the top of my head of why I could never use Apple Mail, and why you may also want to consider Microsoft’s superior offering of Entourage for yourself.

Although in an ideal world, Apple would finally pull it together by fixing all of the above problems, so I could finally switch to Apple Mail and delete Microsoft’s products off of my hard drive once and for all.

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9 Comments leave one →
  1. commun5 permalink
    October 12, 2009 8:46 AM

    Scott: You are, of course, right as far as you go. However, let’s put this in a different context. Apple Mail is supplied for free with OS X. To get Entourage, the Mac user has to pay for Office 2008. And if the Macintel user wants Visual Basic support, s/he must either find a copy of the now-unsupported Office 2004, or buy a copy of Windows and Office 2007.

    Minus the Windows + Office 2007 combination, the Office 2008 user gets an email program that is not the feature-to-feature equivalent of Outlook. And how many people trust Entourage’s database after the notorious corruption and data loss problems that appeared in 2007 and 2008?

    So here’s my challenge for you: if your blog is to be something more than advertising for Microsoft, write a balanced review of Entourage and Mail that examines ALL of the costs and benefits of the two programs in a larger context in which Microsoft and Apple try to sway people to adopt their operating systems based on certain kinds of software.

    With the rapid rise of open and web-based software, the market is rapidly developing to the point where the Microsoft-Apple beggar-thy-neighbor software policies is no longer tolerable to the average user. For Microsoft, it seems to be their primary mode of competition, in place of genuine innovation.

  2. rockitriddle permalink
    October 12, 2009 10:53 AM

    Using Apple Mail myself in a corporate environment (along with 40k other employees), here’s some of my thoughts on some of these points.

    “Send Later” button — I have no idea why Apple hasn’t implemented a “send later” button along with a real outbox like Entourage, so you can queue your messages and send them later. This is a critical feature for people who use email professionally.”

    What’s wrong with saving as a draft?

    “Apple Mail creates an extra folder — that you cannot delete — on your IMAP server entitled “Deleted Items”, even though your IMAP server already has its own deleted items folder, typically called “Trash”.”

    I have never had this happen. Trash is always called trash. You can also specify a trash folder under Mailbox > Use this Mailbox for…

    “Outgoing rules: Entourage can automatically file outgoing messages or do other things to your outgoing messages AFTER they’re sent. Apple Mail cannot. Apple Mail only has INCOMING rules, not OUTGOING rules.”

    For my use, searching a common Sent folder is much easier and more efficient than scattering all of my sent messages across multiple mailboxes.

    “Threads of email messages: Entourage lets you click through the ENTIRE history of an ENTIRE thread of email messages, no matter where the messages have been filed away.”

    I agree this would be great. Gmail actually does an even better job than Entourage at this. For now I just search for the Subject of the email I want. The downfall of both Entourage’s and Gmail’s threaded messages is that it is tied to some header info that can be passed along to other threads if someone replies to a message and changes the subject and body. This happens all the time in the mailing lists I’m subscribed to. So much so that I turn threading off for those folders.

    “Editing subject names of incoming messages…”

    I used to do this with indev’s MailTags http://www.indev.ca/MailTags.html excellent add-on for Mail. However, it became too tricky to keep track of continually changing subject names in long threads and I would ultimately wind up with multiple subject names for the same thread. For a serial number email I would simply search “entire message” for the name of the software or developer and add a boolean AND with “serial”.

    “In Entourage, any incoming or outgoing email message can be automatically assigned the color that you’ve assigned to that contact.”

    While there is no way to color code contacts in Address Book, it’s pretty simple to assign a color via an incoming mail rule in Mail. In my mind, color coding contacts would only work for a very finite number of contacts before shades of color become indistinct and distracting. Besides, if I want to keep an eye out for new mail by specific people I much prefer a smart folder.

    “Entourage has super-robust scheduling that Apple Mail can’t even touch.”

    Not sure I see the point to any of that.

    “When attaching attachments in Entourage, you have the CHOICE of attaching the attachments as EMBEDDED in the body of the email itself OR just as an attachment that doesn’t take up the body of your email. In Mail, you are forced to make ALL attachments embedded in the body.”

    Agreed that this is a nice option. I personally like the fact that Mail embeds each attachment in the message. I always know that a copy of that file in the exact state it was sent to the recipient is accessible. This is especially useful in a corporate environment where a “paper” trail is very important. Of course going to the Sent folder, selecting all and and selecting the Message > Remove Attachments menu option is always there if I wanted to get rid of all of those attachments later to save disk space.

    “Entourage has built-in “text cleanup” options that let you highlight text and then increase quoting, decrease quoting, remove quoting, rewrap improperly-wrapped paragraphs, and change text to uppercase/lowercase. Apple Mail has finally started adding these features in 10.6, but they still don’t compare to Entourage.”

    Quoting handling has been around since at least 10.4 under the Format > Quote Level menu or the contextual menu. I know the keyboard shortcuts by heart. You are correct that 10.6 adds the contextual menu to change the case of text.

    “When deleting an old email account from Entourage, it DOESN’T go through your entire email program like a serial killer and delete all of your email messages that are sitting in your inbox/outbox/sent/trash.”

    It should be noted that this behavior is damaging to to POP accounts more that IMAP, since it does not delete messages on the IMAP server. And Mail does explicitly warn you of what it’s about to do when you delete an account. It would be nice to have an option when deleting an account to archive mailboxes associated with that account before deleting.

    “In Entourage, any email message can be assigned to any number of categories and/or projects that you have setup, which give you the quick ability to search for, file away, and sort those messages later. These things simply aren’t possible in Mail, because categories and projects don’t exist in Mail.”

    Very true. This is why I use MailTags for Mail.

    “Entourage’s “advanced search” feature is much more robust than any sort of searches that you can do in Apple Mail, giving you many more choices than Apple Mail provides for creating a custom search. ”

    I have to completely disagree with this one. Mail’s ability to perform boolean searches has never let me down and Entourage’s searches over 10′s of thousands of messages is still maddeningly slow compared to the instantaneous Mail searches.

    “… and just recently in Snow Leopard introduced an auto-correct (text substitution) feature in its new “language and text” system preference.”

    The feature you’re probably actually looking for is under the contextual menu Spelling and Grammar > Correct Spelling Automatically. Alternately, you can make the text substitution function more robust with this tip: http://db.tidbits.com/article/10567

    None of this is to say that Mail is a better fit than Entourage for any given user. Ultimately it probably comes down to the underlining mantra among all of Apple’s built-in software: simplicity first. The average user can set up and easily use Mail, which in turn integrates into the rest of their consumer software elegantly. Entourage is designed to try to cover every little feature that a power user might want at the expense of a simple user interface. Different strokes.

  3. commun5 permalink
    October 12, 2009 2:51 PM

    One more point. I know you’re likely to respond that you told us in your first posting how much you hate Microsoft, and that you’re just trying to light a fire under Apple. But it’s pretty clear that Apple is not going to make Mail into something that’s even close to what you want. That would only happen if Apple were to take the desktop/notebook business market seriously, which they never have. Since you were willing to buy an Office suite to get Entourage, wouldn’t your efforts be better spent joining the multitudes on the Mac Office blog who are begging Microsoft to release the recently announced Outlook for Mac version of Office as early as it possibly can?

  4. herbertbarrywoodrose permalink
    October 13, 2009 4:32 AM

    Wow – am I glad to have somewhere to rant about this. Finally someone’s saying it and can commiserate.

    Of course, I can’t say this around fellow Mac users because we’re like some weird Mormon cult where we aren’t allowed to question the Father. Listen up guys – I made the switch, I love the product: but I’m not anyone’s bitch, or fool. I paid my money and now they can kiss my ass. In the normal world we complain when things don’t make us happy. Go defend rich guys somewhere else.

    Let me say up top – I LOVE MY MAC. I love my Iphone, I love Apple. Apple Mail blows. OHHHHH it sooo blows. I won’t even OPEN it. I mean it’s there, I haven’t gone the whole leap to removing it from my dock, but I’ve thought about it. The thing is, the one time I couldn’t get into my main email for 30 seconds, I accessed it through Mail. So I keep it, but oh my god what a disaster. I mean, you reference using it as a *business*, Scott? That it’s missing a feature you might need as a professional?

    I’m flabbergasted the thought of using it professionally even CROSSED YOUR MIND. It hasn’t even crossed my mind to use it at *home*!

    Of course, Mac users don’t want to hear it. The slightest criticism (and, this all actually amounts to ‘slight’ – everyone’s in love with the company and the fact that it doesn’t put out a good mail program means exactly nothing in regards to my continued business with Apple) and you get accused of anti-seMacitism. You MUST be a secret Microsoft employee! Because you don’t like Mail. That’s great. Good work genius. Meanwhile I through out my Dell and spent thousands on Mac equipment because of this guy’s relentless proselytizing on behalf of the company.

    The fact is you have to be able to hear it when something’s not perfect. And not only ain’t this perfect, it sucks. Scott was being GENEROUS. You think he wants everyone buying MICROSOFT PRODUCTS?!? The guy shed a tear of happiness when he heard Microsoft’s stock was in the toilet. He wants you to know that EVEN MICROSOFT is running circles around Apple on something as silly as a mail program. You think it’s bad that Entourage is making Apple look bad? My stupid GMAIL is better than Mail, by a long-shot. It’s not even close. I’ll put up with being locked out of it for 30 seconds every 5 or 6 years if it means not even having to open Mail. My HOTMAIL account, my YAHOO account – quite possibly bottom of the barrel services – are better than Mail. And that’s for FREE mail. The argument of “FREE” doesn’t even hold up – FREE emails are all BETTER than this.

    Opening up Mail is like forgetting you have stuffed everything in your apartment into one closet, and then opening that closet wide open when looking for a pen. For a company built on principles of simple organization, bending the product towards the user’s thinking, fun, aesthetics – Mail isn’t even the closet in that analogy – it’s the MESS within the closet. It’s the disaster that comes flying out, that you don’t want your Windows-using neighbor ever seeing, or your work at getting them into a Mac will be set back 4 years.

    I’m astounded anyone at all was able to coherently put together a list of denials, workarounds (why do I want a workaround for something as simple as email when there are only about a thousand services doing email at least poorly, a level Apple isn’t even accomplishing?) and lots of agreements with your post. But the responder was coherent, so I have to acknowledge “different strokes” and let it go. But I have to register the shock. If there’s anything at all that recommends Mail other than that it was FREE (for god’s sakes! what a MICROSOFT response!) then I confess I am blind and am still missing it.

    As for your brief shots at the Iphone – I LOVE my Iphone. But I had a major nightmare occur because I DID NOT want AT&T service. I HATE AT&T’s service. I went to Verizon and tried to make do with one of the plastic pieces of garbage they sell, but ultimately I just couldn’t do it. I made it a week before I had to go back to the store and yell that they were charging me way too close to what I’d pay for an Iphone and I was way too far from an Iphone with that phone. The Verizon service, however, and the coverage, was great. But it’s like having great service attached to a string bean can. I don’t know how everyone’s not on an Iphone, but at the same time I just can’t stand the AT&T service. I have no idea what anyone’s saying, the calls drop two or three times per call, it’s just a mess.

    I agree that Iphone’s continued tie to AT&T is absurd and infuriating. I spent a lot to get out of my Verizon contract (I’m going to fight it, but as an individual I’m officially powerless) and I would have spent a lot to just have an Iphone, even if AT&T wasn’t subsidizing it. AT&T could have continued subsidizing phones on their service, it would be a great boost to sales – I would have paid the full price of the phone not to be forced. I used to feel that Apple was just like the rest of us, tied to an abusive two year contract with a single provider. But I was very disappointed when they signed right back up with AT&T for another go round. I don’t think that’s entirely fair to the customer, and I like to think of Apple as one of the few, rare companies that really looks out for the customer.

    Seriously, you’re better off using any other email program. I wouldn’t recommend Entourage or any Microsoft product, and I don’t really think Scott is either. It’s just that everyone out there is doing this better by now.

  5. June 11, 2010 6:19 PM

    Hi Scott, great post. I just recently bought a Mac and yes still love the Windows email client. Will give Entourage a go and needed your info to confirm purchase! Sin
    http://www.blog.aspirenet.com.au

  6. June 30, 2010 6:07 AM

    that was useful!;D

    i have mail and microsoft entourage both on my mac, but i havent tried using entourage x) er may i ask if anyone knows how to mark different emails in Mail? there probably is a way but im not professional at all so i dnt knw how!:( would appreciate some steps :) another question! is it possible to change the “set up -ed”email in entourage/ mail. If you know how, please list the steps too :)

    Thank you!

  7. nutz321 permalink
    June 1, 2011 7:24 AM

    Whoa, herbert. I don’t think you can go so far as to say that Hotmail and Yahoo are better than Mail. I’ve been using Mail and it’s served me quite nicely. I’d much rather use it than logon to Hotmail or Yahoo.

Trackbacks

  1. Microsoft suffers worst fiscal year ever while Apple rises « ScottWorld Blog
  2. 10 Ways to Soup Up Apple Mail « ScottWorld Blog: My Rants and Raves

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