vs Entourage

It's been a few weeks since I've been on this lovely MacBook Pro. It's a fabulous little laptop. And probably one of the tasks I've spent the most time doing is sending and receiving email.

Keep in mind, this is from the point of view of a die-hard Windows user of many years. I've been using Microsoft Outlook and had really gotten to like the most recent version in Office 2007.

My default view in Outlook 2007 gave me all of my information at a glance: my inbox, a list of favourite folders that I used to track current projects, a quick view of upcoming appointments, and my to-do list which included flagged emails (which could be further categorized by colour).

My first idea was to skip having to use Office for the Mac altogether. I paid for iWorks which gave me all the apps I felt I'd need in the beginning. fit the bill, for the most part. Some things, though, were different from what I was used to. I didn't like that email, the address book, and the calendar were all separate apps. I used to do all of this within a single application.

I do like the design of It's clean and easy to navigate. It's also simple and straightforward and really gets out of your way, focusing only on the important task: the email.

I don't like that nor send responses to calendar appointments that I confirmed and it stops me from moving an event on my schedule that was created by somebody else. In Outlook, I'd be able to move it and then send an update to the person who originally sent the invite requesting a time change.

I hate the way handles attachments by placing big chunky previews right in my email. Ick. I prefer them to be named attachments listed somewhere else, out of the content of my email. (I've since discovered that you can change this via a terminal command.)

There doesn't seem to be support for email to be sent at a different time. It's not unusual for me to be up in the middle of the night writing out an email (or a blog post, as the case happens to be) but I don't actually want to send the email until 9am so that clients don't think I'm up 24/7 and at their beck and call.


When I first installed Entourage, there was an initial sense of comfort. Ah, the familiar 3 column view! But that comfort was short-lived. Overall, the design of Entourage is horrendous. It doesn't seem to follow Mac conventions, the purple accents are ugly (and unchangeable), default font sizes were too big and line spacing was too large. Very little of the interface seems to be customizable.

A number of the elements provide way too much spacing and in other places, not enough. It's missing the favourite folders feature that I liked so much in Outlook, or rather, is now a toolbar but my folder names are longer and sometimes I'd have too many to display horizontally. I just want a vertical list.

It looks like Entourage supports delayed emails but no, I don't think it does. There's a Send Later feature but all it does is send the email the "next time you connect to the server", which just happens to be every 10 minutes when I check my mail. I don't really need to delay sending an email just for that.

I do like how it handles attachments. Being able to see the file names in a list at the top is nice. Why insists on attachments being viewed inline, I have no idea.

And why can't Entourage import from an Outlook .pst file? They're from the same company! Thankfully, it pulled everything in from just fine and the syncing of address book and calendar was nice once I discovered how to enable the feature in Entourage. (I had been busily looking for 3rd party apps to do it when, in the end, I didn't need to do that at all.)

There's a mini-application called MyDay to give you a quick synopsis of your day and can sit in the menu bar but it's also quite ugly.

I have no doubt that Microsoft has plenty of designers and they probably put this application through lots of user testing but, to me, it could use an overhaul from top to bottom to help simplify the application and make it fit better with the Mac aesthetic.

Published December 11, 2008
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Byron Rode said on December 11, 2008

Jonathan, you summed up my thoughts on Entourage exactly.
When I first moved to my MacBook Pro earlier this year, and started using, it felt like I had moved from Outlook 2007 to Outlook Express.

I think I had Entourage installed for about a day, and much like you I was disgusted in the layout, the colours, and the overall chunkiness of the software. As for MyDay, it annoyed me.

Now, is not the best email client I have ever used, and I do feel there could be a bit more development put into the application, but after all it is only really a email client, and as such should be treated that way.

I wish there was a bit more customization available through the interface and not through terminal, but then again, would we not just be restricting ourselves to the M$ way of things.

All in all, IMO still beats and Entourage.

Nice post though, good for the noob OS X user, especially considering the price of Office:Mac.

Nick Jones said on December 12, 2008

So, what's this magical Terminal command for toggling attachment previews on or off? Do tell! And welcome to the Mac; you seem to be getting along just fine!

Martin Hipp said on December 12, 2008

If you prefer to have 3 colums, have a look at Letterbox or WideMail.

j4k3 said on December 12, 2008

Well, the part about Outlook totally reflects my impressions of all the apps in the new office for mac suite.

The term that immediately came to my mind was "Playskool". The whole thing just looks like a user interface experiment that's gone terribly wrong.

I know, packing all functions Microsoft needs for their definition of the term groupware into one program sure isn't easy. But, seriously, how can they fail so hard?

Alexander Chuprin said on December 12, 2008

You also can use WideMail ( to have three-columns view in

Jaimie said on December 12, 2008

I also switched and moved to Entourage when we moved to an Exchange server (it works but is ugly!).

If you still use try MailTags. It is a great little addition.

bcarter said on December 12, 2008

I'm a die-hard mac user, but I agree that the entire,, address needs to be summed up in one functional application. Currently it just wastes time to have them as three apps. Also, has come a long way over the years. It does need to include the iCal and Address Book apps to be truly functional, but the seems to be built very well for just email. I do have some suggestions in the area or email organization, but even Google can't get that right so why expect it from Apple.

Jonathan Snook said on December 12, 2008

@Nick Jones: I thought there was a terminal command but I apparently got it confused with something else. However, there is a plugin called Mail Attachments Iconizer that'll do the trick.

Christian Ross said on December 12, 2008

So which did you decide on?

Jake said on December 12, 2008

I have yet to find a mac email program that makes me say "I like this equally or more than outlook". If you guys have a combo of plugins for that makes it somewhat comparable I would love to hear/read it.

miklb said on December 12, 2008

I'd suggest looking at the beta of Thunderbird 3, and dig up the pre beta of Lightning 1.0. I too have tried every mail app I could find on the Mac, and this seems like the closest thing to the perfect Mac email client I've found.

Mr. Darcy Murphy said on December 12, 2008

At my day job, I'm actually running Windows through VMware in order to use Outlook. It's a hack, but it's workable, and not too bad resource wise.

I haven't tried it yet myself, but Thunderbird with Lightning might be the Email+Calendar solution you're looking for.

Sean McArthur said on December 12, 2008

I personally use Thunderbird with the Lightning Plugin. I find it very simple to use, has all the same features you liked about Outlook, and it's free. It might be a little buggy if you use IMAP, but POP works fine in my experience.

Lightning adds a calendar and tasks to Thunderbird, and you can have each in separate tabs. But you can also easily add upcoming events from the calendar and your todo list into a column with your email.

Andy Kant said on December 12, 2008

I gave up on trying to find a professional email program for Mac, they just don't exist. is a limited email program by design. Running a VM in order to use Outlook 2007 is definitely worthwhile for anything more than personal email.

I would also agree with j4k3 that Office Mac 2008 is pretty unimpressive. The UI for Office 2007 is beautiful, elegant, and simple. What they accomplished is probably the best UI that I have ever experienced, Office Mac just seems like a step backward.

Sarah Jean said on December 12, 2008

I would agree with miklb and others on the Thunderbird/Lightning combo, seems to work pretty well as a replacement for outlook.

I'm an avid Remember the Milk user, so I'd like to see Thunderbird or Lightning accept feeds from RTM without crazy run-around customizations. If you manage all of your tasks within the application and don't need them to also be web-accessible or sync with anything else, then it works really well. Unfortunately, though, Thunderbird/Lightning are still very buggy. (My inbox always says I have 1 new message, even if there are no unread messages in the folder. SUPER annoying.)

NICCAI said on December 12, 2008

For me, the importance of oodles of features inside a mail client is becoming less and less important. Get in, get out. Drag. Drop. Do the deed quick. I don't want it to be a hub for anything. For me, a mix of the Apple apps and the Google cloud is the winning combination.

Karl Swedberg said on December 12, 2008

Another nice plugin for is Mail Act-on. While version 2.0 is $19.95, I haven't had a need to upgrade from the 1.3.2 version, which is offered free on the same page.

Ben said on December 12, 2008

It took a lot of getting used to, but i really Opera as my mail client. I apreciate filters, IMAP, Feed integration, very fast searching, and highly-customizable views. And having seemless integration with the browser, mail client, and RSS reader is not something i would trade for anything.

It has a lot of limitations like a HORRIBLE UI and no support for composing HTML emails. Those two things are dealbreakers for most people. But now that Opera has Jon Hicks as their senior UI designer and is adding rich text email in Opera 10, i think the mail client in Opera 10 is something to look eagerly forward too.

flash tekkie said on December 13, 2008

Apple Mail is also troublesome when it all goes multibyte. There's no solid option in Mail to change default encoding to UTF8 and so the emails that are sent out in German, Dutch or any other language having umlauts, are most likely to break on other platforms.

Matthew said on December 13, 2008


Interesting notes, Microsoft have certainly set a high bar with Outlook 2007.

One app which hasn't yet been mentioned is Daylight 3, which you may want to look into:

It is quite pricey though and requires even more for Mail integration. There is a demo though.

Kevin said on December 14, 2008

I miss the flagging functionality of Outlook :( It makes it so easy to prioritize action-items with a simple click... in I have to right click -> click or cmd+shift+L. But OS X definitely makes up for it with many other productivity enhancements...

Oh, and I like keeping Calendar & separate! It is more flexible in case I don't want to use (I use gmail + I suppose some sort of option to enable functionality in could be useful though.

Eric said on December 14, 2008

There's an AppleScript for scheduling email deliveries -- it's part of Mail Scripts 2.8.3 by Andreas Amann. I haven't tried it, so don't know if it works.

flash tekkie said on December 14, 2008

Matthew: That high bar certainly didn't concern keeping to the promises as new Outlook is still not standards-compliant.

Kevin: Apple Mail flagging from a toolbar flag icon is nicely synced with GMail starred items without using any keyboard magic.
Alternatively you could use Google's own ToDo list in GMail as part of Google Labs.

As in terms of Apple Mail - iCal integration Leopard introduced ToDo integration in Mail. You can attach ToDos straight to the emails in Mail.

Jonny Jaynes said on December 16, 2008

Thunderbird plus lightning all the way, although I've never like Outlook. Great article as always!

Matt Newboult said on December 16, 2008

Can I ask what you dislike about Google Mail/Calendar/To-do list? I used to use Entourage and hotmail but when Gmail came out, it suited all my needs and I ditched Entourage straight away. I use Apple Mail to backup my Gmail and everything is rosy.

I don't understand why you don't just use online email?

KeeKee said on December 16, 2008

We use Mac at work and they just changed our email to outlook express which is what I use on my Dell laptop. It's not the same outlook express!!! I wish they would read this at work. Hey, I have an idea, I'll send them the link from an email they don't know, like my Moms and maybe they'll check it out. Thanks for the heads up.

villageindian said on December 18, 2008

There is a way to do with Terminal. Please check here attachment as icon

Adrian said on December 20, 2008

I know this is a bit off topic but how are you liking the glossy screen so far? That's the one thing holding me back from pulling the trigger for a new notebook. For anything but graphics work, I'm sure it's fine, but for most designers, colors are a big concern.

Jonathan Snook said on December 21, 2008

@Adrian: The screen is so bright you'll almost never notice any glare. I've had glossy screens for 3 years now and it's almost never been a problem.

Adrian said on December 21, 2008

Awesome, thanks for the info!

Eric Angella said on December 22, 2008

I've been looking high and low to schedule emails for the same reason, and can't find a thing. The mailscripts mentioned above by Eric doesn't work since the latest Leopard has a bug preventing launching applications from alarms in ical. But I would throw in a vote for the + add-ons method of email management. Mail Act-On, Mailtags, MiniMail, MsgFiler, and Widemail together is a pretty stellar combo. There are many more here.

Ryan said on December 27, 2008

I switched to Entourage because I thought I might be able to use it's project tracking to manage projects. After a while I put up with the shortcomings and update issues... until one day my IMAP just went AWOL and I couldnt access my new e-mail, just my cached mail. I had to delete the caches and all this garbage and well.

I realised it just wasnt what I wanted - I wanted a simple email client for sending email. So I use gmail and Mac Mail :) In fact I use gmail since it fell over and have not turned back...

I do miss drag and drop attachements though, send and forget isn't quite gmail....

smudge it said on January 04, 2009

Thunderbrid is my favourite mail app. I find mail is quite slow with huge mailboxes and didn't seem to work that well with IMAP. Maybe it has improved a bit in the last year. My app is still Thunderbird

jason said on January 09, 2009

This is a month old, but just thought I'd throw in my preference and the main reason why. I prefer over entourage. The main reason, if you store any mail on your computer at all (I use iMap, but I keep my folders on my Mac and drag them off the server when organizing) is better. In the library, the folders and emails are separate files, which may not be as efficient, but if an email becomes corrupt you just delete the bad guy. In entourage you (and I have) lose all your mail if the file or the microsoft identity gets corrupt. I guess if all your mail stays on the server this shouldn't matter.

Cris said on January 11, 2009

At Duo we use our imacs with vista / xp running in parallels. This combined with mac spaces is a great developer solution. You can use one of your spaces for full screen windows and cmd+cursor keys allows you to switch between them. On some of our machines we run vista and a default xp install to get IE6,7 and MS Office 2007 all at the same time. With 4GB of memory installed this works really well and allows us to develop and communicate via dedicated spaces. I just wish there was a one key solution to refresh all your browsers on both platforms. I had to disable ctrl+f5 on mac as it kept switching on screen reader instead of a pragma-refresh.

Calendar wise we've installed ical GPL server on a linux box which gives us a very simple shared calendar solution for our 5 staff via ical, we also run an exchange server but the whole sharing permissions thing with calendar was too much of a pain to set up ( i hate MS Server Admin, too used to Linux I suppose). I think we may drop outlook in favour of mac mail when it supports exchange, our iphones already use the exchange server beautifully, perhaps snow leopard will deliver a more professional angle on mac mail, who knows? With anything, it's what you are used to. But parallels + spaces is very cool. If you don't want to buy parallels I hear Sun have done a free virtualisation system called virtual box. Could be worth checking out.

Bradford C. said on January 16, 2009

I too am using Outlook 2007 via VMware fusion. I'm not happy about it, but it's the best solution I've found so far. I need the event management and the Zimbra integration in general.

Scott Meier said on January 18, 2009 Attachments
If you ctrl-click on the attachments you can change the display at the email to view as icon. You don't need to go to the command-line for this.

Email sent at a different time...
There is a folder called Drafts. Just save it and send it later... ;-)

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