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