Microsoft Entourage vs Apple Mail, Address Book & iCal

Here is a common and very good question, which contact management suite should I use? Well if you haven’t purchased Office for Mac 2008 then the answer is pretty obvious, you are going to be using the Mac included contact management solution that consists of three separate programs: Mail, Address Book and iCal.

Now if you purchased Office for Mac 2008 you may just be thinking to yourself, I want to get my moneys worth so I may as well use the included MS Entourage Contact management program that seems very “Outlook” like. I’d say the best thing Entourage has going for it is it’s resemblance to Outlook so it may feel a bit more comfortable to some Switchers. There in lies the trap, “familiarity”. If “comfort or familiarity” are the main reason you are considering going with Entourage you may want to think again.

Apple Mail Address Book iCal

Now I don’t want to seem like an MS basher but there are some things that you will need to consider before committing to using Entourage, and by committing I mean committing because once all your email, contact lists and calendar events are imported into Entourage it’s not going to be fun having to move them over to Apple’s Mail, Address Book and iCal.

So what about getting your Outlook data over to the Mac, wouldn’t it be easier to move Outlook data into Entourage rather then Apple’s contact management solution? The short answer is it’s the same solution for both, I strongly suggest you pay the $10 to Simple Machines and use (O2M) Outlook to Mac for the heavy lifting. You will shave off hours of your time and the end result will be all your contacts, email and calendar info transferred into either Entourage or Apple Mail, Address Book and iCal – your choice.

Both the Apple and Microsoft solutions will work well and will do most of the same things so what do I suggest, I never thought you would ask? I say go with Apple all the way and here’s why.

Apple has really cranked their included contact management software up a notch in Leopard with new features like: Mails Stationary and Photo Browser, plus the ability to preview with Quick Look and save groups of photos right into iPhoto. Address Book may seem simple to look at but it’s really a very solid contacts program and the fact that every field is searchable and its Address Book is fully integrated into the core of Leopard makes sharing its data base with other programs seamless. iCal now allows you to link files to events and can turn even the most cluttered work week into a very easy to follow timeline.

Some other things you may not have considered when choosing to go with MS Entourage for Mac 2008 over Apple’s Mail, Address Book and iCal. Do you have an iPod, iPhone, .Mac account or any iSync compatible device or maybe you plan to get one in the future? I can guarantee that Apple’s included contact management suite will synchronize all your data much more effectively than Office Entourage will. Sure there are 3rd party ways to do just about anything but these just add another layer of complication and potential incompatibility to the equation.

Here is a case in point, I find it necessary to use a more full featured contact management program for my business and so in my research to find a program that was truly Apple compatible I discovered Contactizer Pro which is an amazing contact management program that works in harmony (the data is shared between both programs) with Apple Mail, Address Book and iCal so I have seamless synchronization with my iPhone and .Mac account, and if tomorrow Contactizer Pro where to throw in the towel (crazy talk) well at least I could fall back on my Apple solution as everything is all right there.

Another thing I like about Apple Mail, Address Book and iCal is the fact they are separately running programs, they look inside each other but can be launched independently meaning I can open just my Address Book if I want and not get bombarded with 50 new email. Another advantage to this is being able to use “Command-Tab” between the three running programs quickly and easily, with MS Entourage I can open a window for each (mail – Contacts – Calendar) but I would have to use Exposé to shuffle between them which would require a mouse click for selection rather than a key command which is much faster.

I’m not done yet, I bet you love Time Machine and its ability to dig deep into your mail and contact data just incase you erased that important email or contact a few weeks back and now you need it! Oh I’m sorry, you’re using Entourage? Entourage is just not supported in this manner with Time Machine, you could replace your entire Entourage contact management data with the data from two weeks ago but that wouldn’t be very useful..

When you invest in Apple you are investing in a company that is committed to making all of its product the best in the industry, they have everything to gain by doing this. Microsoft could pull the plug tomorrow if they wanted to and then where would you be? My point is this, Apple Mail, Address Book and iCal really hold their own when compared to Microsoft Entourage, if your only reason to go with Entourage is familiarity please do yourself a favor and take a look at what Apple offers in this area, I believe you will be pleasantly surprised…

This post was originally authored by Mike Kaye

Comments [31]

  1. Having been a Win user all my life up until recently when I converted to Mac at home, I was keen to install Office for Mac 2008, thinking (and hoping) that it would be an identical twin to the Win version that I've been used to for many years, so I can definitely relate to this issue.

    Disappointingly, I have found Entourage to be a very poor cousin to its Win version eg inability to drag emails into say calendar to create an event, difficulty in handling alias email accounts with same ISP, one rule to either download pictures in emails or not without being able to indicate particular senders are 'safe' and it's ok to show those images etc. So much so that after a brief flirtation with Entourage, I have gone back totally to Apple's Mail, Address Book and iCal.

    The only thing I have yet to manage to change back is to have Apple's Address Book come up as the default program when I want to save contact details from Mail – unfortunately, it still thinks the default is Entourage and ploughs ahead opening that. I'm having to do it the manual way by specifying each time that it should be opened with Address Book, not Entourage. Any tip on how to change the default would be gratefully received!

  2. Thank you so much for the reivew, and the response by katherine.

    I was debating over the all the issues that are listed here. I may have saved my self a few hundered dollars.

    I am going to try the suggestions listed here and then go from there.

    My only question is what do you guys use to open word, excel and powerpoint ?

  3. Wow – I am sitting in front of my new MacBook (its gorgeous), My old PC, and my USB drive (formatted correctly, thanks for the info) and wondering why the hell I paid for Office for Mac 2008. Its installed, but I think your article has convinced me to use Apple everything..

    I have a ton of information in Outlook (calendars, contacts etc) that I can't live without, so I will get the O2M software you suggest.

    I am actually embarrassed for Microsoft as a once great company. How can you sell Entourage to me at a ridiculous price and not allow me to 'one click' import all my data from Outlook.

    I am so mad my ears are steaming, but the light at the end of the tunnel is my computing life is about to get so much better.

    I am living on your site, it has been the security blanket I have needed during this switch.

  4. Great information, just what I needed to decide about moving Entourage to my MacBook or reconsider Mail. Thank you for that.

    Having used Mail first on my iMac and then moving to Entourage (previously using PC and Outlook) I have experienced several pains, especially when synchronization comes up between Entourage and Mail / Address Book / iCal or with any hand held device (PDA or mobile). As far as I could figure it out, Entourage could only synchronize with my Nokia mobile through Mail / Address Book / iCal as intermediator, probably due to Apple's general synchronization mechanism. This is painful as I ended up in duplications all over the place both in my Address Book and my Calendar.

    If my observation is right, same synchronization issue arise when considering the use of .Mac or MobileMe, which could come well when one would opt for remotely synchronizing two or more Apple computers' contacts and/or calendar databases. Such would be hardly possible with Entourage, unless again through indirect ways.

    I have though certain questions yet to be clarified with regards to the efficient use of Mail / Address Book / iCal. For example I used to organize my mails into folders and sub folders for easy access and archiving. I could not figure out yet how this would work with Mail.

    Having said all of that I am sure that there are circumstances, when Entourage would be the ideal solution. The question that interests me in such likely business like use scenarios is whether you could "switch off" (or even uninstall) Mail / Address Book / iCal in such cases, to avoid unnecessary duplication or confusion. I would not be surprised if this later would be scrap idea just because you would then have no ways to synchronize your data.

  5. I just recently purchased an iMac after using a PC for 25 years. I have ordered MS Office 2008 for Mac but now, after reading this piece, questioning whether it would be better to use Office for Word, excel and PP only and let contact mgmt be handled by the Mac. Does that make sense? Can it be set up that way?

    Thanks for your thoughts!

  6. After I made the switch from PC to MAC, I was hoping to stay on familliar ground and installed "Office fo MAC". After I read the original entry I decided to heed Mike's advice and decided to use "Mail" instead of Etourage.

    I am strugling with Mail. Although, it has some nice features(stationary, photo browser), I am finding that, when I am creating new messages, the editing functionality is very poor in comparisson to Outlook. I cannot formatt pargraphs, line spacing edit doesn't exist, the tool bar is very limited and one has to go looking for more advanced features. Spell check is another poor cousin to Outlook. Handelling of Attachments is bit confusing.

    Address book has its own down-falls. Although it is able to sort contacts – One must go into "general" preferences, the sorting is bit confused. 90% seems ok but than it decides to handle some entries in totaly ilogical way.

    Apple could enhance the way the address book looks, considering the other well designed programs. Adding alfabetical tabs, like on my iPod touch would make search easier that the curent search function. I guess I could go on, but you can guess that I am not 100% sold.

    I just hope that Apple will take mercy on us PC switchers, who feared Vista and accepts us into their fold, by providing not just great graphical environment, but also user friendly business place.

  7. I've been using Entourage from MS Office 2008, but I've had it. The post above says it's "not easy" to switch everything to Apple. So how do I do it?

  8. Hi, I just switched to the iMac, it's going to take some getting used to! One question….can I still use my outlook email address in mac or is that address finished now?!

  9. To switch from Win to mac is a nightmare, in particular when you have a lot of data under Outlook. Entourage on Mac is a bit under Outlook on Windows, but far better than Mail, iCal and Adress Book on Mac. I agree totally with Jan Hermann : Mail and Adress book are very poor when you need a professional service. And the management of Tasks by iCal is simply deficient.

  10. I'm transitioning to a Mac Pro for my home but still have a laptop PC for work. I also don't like mac's Mail. I'm looking at using Thunderbird. I've found a lot of the transition challenging, but I'm hoping that by the time I figure it all out, I'll be better off than I was. I use Google Calendar for my personal appointments. I've not been using Outlook as we use GoldMine at work. I am still wondering about which contact manager to use. My friend recommended Entourage but synching it with the Apple programs. I'm still trying to figure it out.

  11. Twice I spent days researching and importing data from iCal, Mail and Address Book into Entourage. Twice, after many hours of importing my data all of my contacts and emails are gone.

    My iCal items appear because Entourage calendar items sync with iCal, they aren't imported – they are synced. So as long as I have iCal open, the calendar items also display in Entourage. I don't see the purpose of having Entourage open if I have to have iCal open too.

    Data I spent hours importing from Mail and Address Book is not showing up in Entourage. To make sure e-mail and contact data weren't going to disappear, the second time I imported e-mails and contacts I imported a few shut down Entourage and reopened it to make sure the e-mails and contacts were there. They were, so I spent hours importing the data for the second time. Turned off the Mac, started the Mac the next day went to Entourage and all e-mails and contacts were gone as if I had not done the hours of carefully importing data for the second time.

    What takes so long to import the data? The best method I read about for importing contacts from Address Book to Entourage, is to click and drag your contacts from Address Book to the desktop, then the desktop to Entourage contacts. But the notes do not import. Therefore, I went through almost 400 contacts cutting and pasting the notes.

    Another thing that took time is figuring out how best to import e-mails. For example e-mails in Mail's inbox did not import so I created a folder called "Inbox Import" dragged e-mail from Mail's Inbox to the "Inbox Import" folder then exported and imported the e-mails into Entourage. There were several hangups such as this.

  12. I've been a Mac user since 1986 but a Windows user at the office since 97. I've just recently switched to a Mac at the office and find the switch is simplest when simply adopting Office for Mac. Entourage is an adequate replacement for Outlook. An attractive feature in Entourage that does not exist in Outlook is the Project window, which groups emails, contacts, calendar events, tasks, and files that are related to a given project created by the user. While not a true project management tool this is a useful feature for which i've not yet found an adequate replacement using Mail, AB and iCal. I should also point out that Ross does Entourage a misservice when he states that one cannot easily switch windows in Entourage – it is as simple as command-tilde. It has become as much a reflex for me as command-tab.

  13. I simply don't agree. Mac's email is awful. I've used it for a month [Im a long time PC user] and can't stand it. Don't let one man's opinion scare you off from Office for Mac. Mac users tend to have a screw loose anyway when it comes to anything Microsoft.

  14. I don't think you should pick on Entourage for not being about to comm-tab, on a pc you can comm-tab through all your open windows, not just 1 selection from each app. i'm finding that incredibly frustrating to get used to. there are so many more clicks and buttons to press (don't even start me on FN DEL).

    You also didn't mention how foul it is to have to drag photos into the body of your msg (in MAIL), rather than attaching them like a grown up. It's so child-like to send emails with big pictures, thank god they don't show up like that at the other end, how embarrassing would it be.

    At this stage I just don't know which one is better, both annoy me.

  15. Thanks for the honest article — I also just switched to an imac 15 years of using a PC. The transition has been a little difficult, but well worth whatever pain I go through. I am loving my new mac. Meanwhile, the question you brought up was precisely the one I had… Should I use Entourage? I think I will uninstall the MS Office 2008, and take the time and energy to try the programs that are native to Apple instead. I want to simplify my life — and in-so-doing — make the most out of the powerful tools that are already existing on my mac OS. Thanks again for the honest words…


  16. I found this article supremely useful. I'm just making the moveover from PC to Mac and was told to avoid Entourage when migrating mail from Outlook. I initially thought this was just diehard MAC-speak, but having read this, and considered that if I'm going to make the move to a MacBook Pro, I may as well make a full move to Apple, I feel much more reassured that migrating my data to Apple Mail will be the best decision – even if I'm not familiar at first 🙂

    Thanks a million,


  17. I was able to easily transport information from MS Outlook 2007 to my Macbook Pro's MS Outlook 2008 Enourage using my Blackberry. You have to choose some settings in Entourage first, then the BB desktop manager will ask for settings, then sync. I got everything, including my notes, which do automatically sync with the Mac programs installed already (iCal, etc.). My question is, is there a MS Notes-like program for the MacBook that is not connected to Entourage for when I get my iPhone?

  18. Hi Mike,

    Mac Mail is good, but have you noticed that your signatures come up as an attachment in EVERY email you send out?

    It's driving me nuts. I'd switch to Entourage just to fix it. Mac has been unhelpful in showing me how to fix this signature glitch that Outlook users don't seem to have.

    Do you know how to stop your Mail Signature from sending as an attachment?


  19. Just a quick thanks for a very helpful article. I've been using both Entourage and Apple Address Book for too long and am finally moving everything over to Apple. I just love the Entourage project features so its been a tough choice.

  20. Thanks for the help. I will stick with the MAC products just to keep it simple.

  21. I have successfully transferred all my emails from MS Outlook to Mac OS Entourage. Once i lost my data due to corruption and then fixed the issue effectively using Database Utility.

  22. Awesome write up.. I was just about to import from Mac Mail to Entourage and then I read this and cancelled the import. It made me realise what I have come to love about Mac Mail, iCal, Calendar; that they all talk to one another but can run independently.

    Thanks again!

  23. Honestly, I have been using entourage 2008 on the mac for about 2 years now and i can attest to its awesomeness. I think u're bashing it way too much.

    It's email backup is amazing. Apple's mail is OK! but for more advanced stuff and options, u can't go wrong with entourage.

  24. Now that I run three small businesses from home, I figured I should "start over" and use my Entourage for a change. Something told me to look it up and to be honest, I don't need to read any other reviews, because you did answer every single question I have. Thank you so much and keep writing! ~Teraisa

  25. Very informative (and timely for us) article.

    I’ve used the MS suite for Mac for years, and loved it. However, when I started using version 2008 with my new Mac Book Pro, I began having big problems with it. Lot of crashes. I contacted MS and reported this concerns and they advice me to save a back- up, and and reinstall. Sounds easy, but it a pain to do have to do it every other day because it continues to crash.

    I was thinking that all I needed to do was to upgrade to the most current MS Office 2011, but the reviews on it for the most part were that it is worst than 2008? Bummer, I really like the application, but, just very frustrated with the crashes, data lost, and reinstall stuff.

    So, I’m considering just going with Mac designed and based software: iWork. Apple Mail, Address, and iCal. I still think MS Office has more advanced features that these Mac applications, but what the point if you can depend on them to work for you?

  26. Hi, long time ago I was curious about entourage so i started using it. But after a while I decided to go back to i cal. Now I have an entourage calendar in my ical which after many many times of trying to delete it, comes back up, and seeing it there annoys the heck out of me. Is there a way to get rid of it?

  27. I agree with Tai. I've used Apple mail for six or seven years and have always had a love/hate relationship with it. Entourage, which I use at work, is now my choice for use at home. I'm all about Apple products and Macs, but here I break ranks. (Well, I have a Blackberry, too, but don't tell Steve Jobs.)

  28. Of course the irony of this article is that Microsoft is the company that provides the most support and MOST certainly more than Apple who does drop support at the drop of a hat (just like they did for Apple rack servers). Imagine being the IT guy who recommended that to his company. On the other hand Microsoft has been supporting their technologies as a company should. Take windows XP with over 10 years of support.

  29. Although late after the start of this thread here’s my ten cents.

    Working on quite complex projects with a myriad of events, documents and contacts, I found Entourage to be a great system to keep everything (including myself) organized. With 1500+ contact and even more documents to keep track of in place, time and referenced persons, it was not easy to do this in my favorite (Apple) applications. In Entourage however, the ability to interlink notes, tasks, calendar-events and contacts to each other as well as linking to external files of all types, eases the managing of my tasks.
    I am a vivid admirer of the Apple looks and functionality and would definitely cheer an Apple dedicated application that would do the exact same, but this seems simply not the case yet.
    Entourage (unlike its follow-up Outlook) does an excellent job and for me outperforms the Apple iCal,AB and Mail combination.

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