Apple Mail vs. Entourage with Exchange Server
Jim Mock at SoupNazi.org writes about his experience of using
He writes about three reasons to dislike Entourage (”the bastard step-brother of Outlook”) — anti-aliased fonts, forced line-wrapping at 76 characters and default top posting.
And he begs the Apple Mail development team to build
I feel his pain, naturally, but I could read posts like this all day.
Tags: Email Client, entourage, Exchange, imap, mail.app, MAPI, retarded IT departmentRelated posts

January 14th, 2006 at 10:29 am
The irony is we’re going BACK to entourage soon — mail.app is dragging horribly with IMAP, and address book + ical is not strong enough collaboration, and ical especially is rough after more than 10 calendars. So while I agree that Entourage sucks visually — it’s more robust in a group working environment, I hate to say it. It’d be the first time I’ve stepped away from an apple product:(
January 17th, 2006 at 5:01 am
Hey, I work on Entourage at Microsoft… I realize that parts of the app feel dated and slow at times. But what would really help us is recommendations from you and other users about how we could make the app look better. Just post, I’ll read and share with the team!
January 18th, 2006 at 12:58 am
functionality-wise, entourage seems to cover most functions I need.
The worst thing about it is the horribly over-complicated interface. There are far too many buttons on the toolbar, and the Search needs to be emphasised better.
The sound sets are awful! I turn them off straight away.
I would rather Entourage showed the number of new emails in its icon (ala Mail) rather than popping up annoying windows on the right of the screen.
HTML Signature support is lacking. Our company has a HTML signature which doesnt work in Entourage because it uses tables.
Please put all the preferences together in one panel. Rather than a mish mash of Preferences, Accounts, Rules, Signatures, Junk Email settings etc.
There are far too many options to choose from in the drop down menus (file, edit, view, message etc.) Wouldnt they be better off group under “flyouts” inside the menus?
Can I use contacts that are already in my address book rather than adding seperate ones just for Entourage please? Its annoying that Address Book has all my contacts and yet when I want to send an email in exchange, it doesnt pick up on these.
On a related note, linking the built in calendar with iCal would be great.
On the other hand, there are things that Entourage gets right that Mail.app doesnt. Exchange support is spot on, the project management features are useful, and the junk filter is very good.
Some of these points may already be included in the application, but perhaps they are not intuitive enough because i have failed to find the options for them.
Ok, winge over :)
January 18th, 2006 at 4:22 am
A few things come to mind right off the bat:
1) For the love of god, *please* make the line wrap configurable. Having it forced to 76 characters mangles the quoting in replies like crazy (and having to rewrap paragraphs every time is getting old) and makes it impossible to read.
2) Don’t anti-alias text that shouldn’t be anti-aliased. I read a little about the reasons why it’s being done (a side-effect of using Apple’s ATSUI text engine and Carbon apps - see http://www.newgeo.com/index.ws?id=100008), but still… there’s got to be a way to fix it.
3) Add the ability that Outlook has to read everything in plain text.
Those are my main complaints. If I think of anything else, I’ll post a follow-up :-)
January 18th, 2006 at 4:38 am
iCal & addressbook, and Apple Mail are fine, but aren’t serious products. The only things I miss about Windows is Outlook. I used to use Entourage regularly, but stopped using it when I started to use iSync (and Entourage didn’t support that). I would love to see Entourage have a real Mac “look & feel” but all the functionality of Outlook. Microsoft does incredible apps, but of late the Mac apps aren’t that great (and I understand why). Instead of just ceading this terrirory to Apple and other developers, I would encourage you to create a worldclass mail product for the Mac that will draw people back to MS Office!
January 18th, 2006 at 9:59 am
I just switched from Entourage back to the Mail/iCal/Address Book combo for the umpteenth time. I love the integration in Entourage (and Word/Excel/etc. as well). The project management features are just the right level for the type of projects I handle (no need for Gant/Pert/finance/time tracking). I can switch to a project’s view and immediately get a filtered view of relevant events/tasks (my primary jump point)/notes/email (a big one)/files (another big one).
However, there are two categories of problems I have. One is the general slowness and strange bugs/behaviors that always show up eventually. The other is a set of key features that are missing and extremely important (and some minor gripes as well).
First off, the bugs. Currently random button/menu/drop-down/etc. gui elements will show up “grayed out” (I can provide screen shots). Sometimes its the controls on a new email, sometimes it’s in the project view, sometimes it’s the tabs on a contact, sometimes it works perfectly fine. Restarting the program will fix the issue temporarily, but at some point it always comes back. Last time I switched because I had a project that, when switched to, would cause Entourage to play volleyball with itself for about 45 seconds (it wasn’t an excessively large project or one with lots of files either). The time before that it decided to duplicate my calendar events one day…all of them, one day I started the app and I had 2 of everything, which I had to manually (painstakingly) remove. I don’t remember the time before that, and I’ve not yet hit the 2Gb db size which seems to cause people all sorts of other issues. This is really the main reason I switch from Entourage…I need stability above all else because I’m trusting this piece of software to manage virtually every aspect of my day-to-day work life. This is also the reason I switched from Windows. I got tired of the 3month reinstall ritual to keep things running…plus I’m a sys admin so having unix under the hood helps my zen level :) and I hate the fact that on windows installing most apps causes junk to get sneezed even into the deepest entrails of my system, and you can never be sure you’ve gotten rid of *everything* (e.g. CLSIDs, empty dirs, orphaned reg entries, etc.) despite valiant efforts by many registry cleaners/etc. I’m a big fan of compartmentalization when it comes to software design (under the hood anyhow).
Now on to part 2. Some of these are behaviors that are practically bugs, others are just annoying or unexpected, and others are missing/poorly functioning and crucial:
- Delete a few emails then hit undo…One (sometimes 2?) emails will come back, after that…nothing. Surely in all the RAM Entourage is guzzling it can find a place to save the last 5-10 actions.
- Adding contacts to the mailing list manager (poor documentation here, but neat idea) and/or to my address book still doesn’t allow images in their email to load without me having to manually download images.
- The notes field of a contact/event/todo should be as feature rich/capable as the notes field of a note. Why can’t I paste an image? (i.e. map to calendar event) I realize I can create/link a note, but this seems wasteful.
- Links should be more prominent. Link to existing whatever needs to help me find what I want to link to. e.g. Link to existing contact brings up the most minimal contact list/table possible with no way to search through hundreds of contacts to find the one I need.
- Which brings me to search. It’s as if no index is ever created, searching through a few thousand emails takes waaaaay to long and then if I repeat the search, same thing again. Spotlight is already there and works well and fast so why not allow it to index Entourage data.
- If I highlight the 3rd email in a list, then hit delete, the selection should stay at the 3rd element in the list if there are more elements, not jump to the second. This is very irritating when trying to “skip” a couple of messages then one-at-a-time preview/delete the rest of the list because I keep having to remember to press the down arrow first to reselect the position I was at…and if I delete a few before I noticed (I work very quickly), then thanks to the limited undo I have to go manually retrieve the message from trash…which there’s no way to sort by “most recently deleted” so I have to dig (search would take minutes)…etc.
- Chris mentioned the junk mail filter, one problem I have frequently is that I have to repeatedly add the same domain to the exclusions list. It appears to be filtering on more than just the domain of the email of the sender.
- I personally have few issues with the interface. My main gripe is that it’s not “standardized” like most mac apps (but it’s Microsoft of course, so no surprise there). I think alot of problems would be solved if people could customize the toolbar button and if unused menu items disappeard after awhile to a hidden part of the menu.
There are more, but they are more minor and probably border on obsessive :)
Basically it’s very frustrating because I think it could be a great product, but it lacks the stability I’ve come to expect from applications I use daily.
January 18th, 2006 at 10:14 am
Search:
Search is not intuitive. It downright doesn’t seem to work at all sometimes which is very frustrating as an end user. I can’t wait for integrated Spotlight Entourage searching as promised by you guys.
iSync:
No iSync integration? Whats up with that? If you aren’t going to port ActiveSync on the Mac then at least support whats already a sync engine in the OS (iSync). I think i have heard this is in the works but seeing as iSync has been out for so long what has taken so long for a business decision to be made on this?
Contacts:
Why are there separate contacts for “on my computer” and “Exchange” servers? That was very confusing for me for the longest time. I expected a similar Outlook experience.
Email:
Why don’t Rules work reliably? Why do they work for a while and then stop working?
General:
IF YOU MAKE A BUSINESS DECISION TO DEVELOP FOR THE MAC PLATFORM THEN DEVELOP FOR THE MAC PLATFORM! We are Mac end users…and some of us still use Windows. Its a no brainer…there is no “business decisions” here. You either develop for the platform or you don’t. The market share can only grow. It won’t get any smaller from what I can foresee.
January 18th, 2006 at 3:14 pm
Second the overly-complicated user interface.
Andy, sometimes my users can’t figure out what seem like obvious things–because of the clutter.
UI improvements alone would make a big difference. Say what you want about Mail–I know it does like a tenth of the stuff Entourage does–but it’s easy to use.
January 31st, 2006 at 6:28 pm
re: I would encourage you to create a worldclass mail product for the Mac that will draw people back to MS Office!
why on earth would any sane mac user want to be drawwed back to MS Office ? ROFLMFAO
that’s an insult to all Mac users, instead you should be on Apple to make a better mail app.
forget MS they will be out of biz soon enough, mac is here to stay
February 2nd, 2006 at 1:10 am
I’m currently hesitating, should I quit Mail for Entourage ?
I don’t like the interface widgets, sure (but you enventually get used to an interface), I would miss Spotlight too, and I prefer iCal (for just one thing : you create new events directly on the calendar window, there’s no new window popping up). Yet I enjoy the three columns interface (I have a wide screen). In fact, the real reason I consider switching to Entourage is the real HTML mail support.
I think I’ll wait for the next update, I’ve read it’s coming out soon…
LJ
February 2nd, 2006 at 1:38 am
Louije wrote:
I agree that the new version of Entourage will make it much more attractive. Did you see this post about the new version having Spotlight and iSync support?
I like the three-pane layout too. There was a mock-up of Mail.app with three-panes on Flickr recently. Looked good!
February 2nd, 2006 at 2:28 pm
I’m a recent OS X switcher and a seasoned Windows consultant. i have found the switch to Entourage (w/ Exchange 2003) pretty seamless, but there are things i miss — a few things:
- integration w/ desktop search aka Spotlight (or maybe i’ll just wait to see if GDS comes out for OS X)
- ability to type in dates instead of always having to pick or use arrows (next thursday, tomorrow, 2 weeks, etc.) just like Outlook for Windows — this is just damned convenient and very Mac-zen like!)
- .PST import directly — speaking of which please allow for ‘virtually’ unlimited mailbox size (i just saw in a previous post that Entourage has the same 2GB limit as non-unicode Windows .PST files — BAD!!!)
- (auto)archiving capabilities
- auto-compress option for pictures (.jpg’s) when adding attachments (like ol2003)
- color code emails (ala o2k3 ‘organize’)
- RETURN RECEIPTS (why oh why is this not implemented?)
hhmm.. sure i’ll think of more, hopefully i’ve joined soon enough to actually impact the dev team to offer these functions… tia!!!
February 8th, 2006 at 4:51 pm
add the “organize” function that ol2003 has. it’s been useful for calendars and emails — especially how you can create rules to do it — categories is nice.. but simple rules are easier to automagically create.
February 10th, 2006 at 3:21 am
Entourage is a nice IMAP and POP client, but even after SP2 it’s still a middling Exchange client… as in it sucks.
Distribution lists, distribution lists, distribution lists. Why on Earth do we have access to our contacts, but not our DLs?!
It would be nice to be able to delete the “* on my computer” stuff. It just confuses the end users and makes an extra support issue.
Security problem: It would be good if one couldn’t read one’s mail without logging in.
synching. Seriously, why aren’t you guys using MAPI?
KERBEROS SUPPORT.
February 16th, 2006 at 6:35 am
There are so many things that I *LIKE* about Entourage — and I *VERY* much would like to use it — but it’s becoming so unwieldy…
I get a *LOT* of email — most people just kind of shake their heads — I’ll handle somewhere in the area of 1,000 emails from people a day (that doesn’t include automated emails, emails from servers, auto-generated emails — that’s just email from human beings). It’s what you get when you have an international server environment…. people all over the world want my attention….
anyway — moving from folder to folder takes longer and longer every day — I keep myself as trim and fit as reasonable, but even keeping a weeks worth of email means that by Tuesday afternoon I’m bogging down.
I would love it if the interface was more Mac, but can live without it. The configuration is unwieldy and enormous, but once I get it set up, it’s usually good to go… It’s just the application’s inability to deal with large mail folders that’s killing me… anything that can be done to make it faster would be much appreciated….
February 25th, 2006 at 10:28 pm
Here’s what we’d like (we’re one of the rare firms in Wall Street that use Macs!):
- Integration with spotlight
- side-by-side calendar views ?ɬ† la Outlook
- Shortcuts for inboxes in the folder pane ?ɬ† la Outlook
- Customizable Menu Bars and Tool Bars ?ɬ† la Outlook
- Easier access to profiles
February 27th, 2006 at 10:19 am
I’m relatively new to MAC (just got an iBook as a gift from my husband). We are both loving Entourage, for the most part, but there are a couple of key features missing.
First, the “request read receipt” feature which is available on Outlook (it lets you know if/when your e-mail was read). This is exteremly handy if you think you’re experiencing technical difficulties but have sent time-sensitive messages.
Second, it’d be really great if there was an option to send an “Out of Office” automated message for when I’m out of town or otherwise unavailable to respond.
Others, I’m sure have already mentioned this, but after Mr. RugBurn switched to Entourage and pulled all his e-mail from his server, Entourage crashed and corrupted his database file beyond repair. All was lost before we even had a chance to back it up. Not sure how or why this happened, but I’ll bet we’re not the first to lose everything.
Thanks for the opportunity to improve a “good” product that has the potential to be really great.
Cheers,
EmRB
March 22nd, 2006 at 3:47 pm
I just left Mail for Entourage and am quite liking it actually, but how about making the spotlight feature a programme-internal one like you have in iTunes, iCal etc.? Much better than doing a full spotlight search that brings up every-singe-document-and-file-and-folder-and-email-and-meeting in the computer. Also, frankly, that search bar in Entourage is ugly. I know we all sound ilke ponces to windows people, but please give it a nice looking one like you get in other Mac apps.
Go on, be daring… make it look/feel at least a little like a Mac programme. We all bought macs with the wonderful visuals partially in mind, and MS have to remember that, because heavy Entourage users spend a lot of their day looking at something that is a bit disappointing. Absolutely love Office 2004 otherwise though :0)
April 3rd, 2006 at 8:02 pm
Entourage has a 4GB limit to its email database. Can some knowledgeable soul tell me if Apple Mail have a limit to its database too?
I used Entourage and I keep important emails from umpteen years ago for reference. Recently my email database reach the critical 4GB limit and I deleted quite a lot of emails before compacting the database. To my surprise the file size did not reduce.
Now I may have to abandon Entourage because I have reached its DB limit.
Any comments???
April 3rd, 2006 at 8:13 pm
Mail.app is a terrific client ;-)
April 3rd, 2006 at 8:16 pm
Sorry. A cheap shot. I don’t really know all that much about Entourage.
Have you tried everything in this list on the Entourage Tips web site:
http://www.entourage.mvps.org/database/reduce.html
November 17th, 2006 at 3:49 am
We switched from Exchange to Kerio Mail Server which has an Outlook-like MAPI portion. Outlook users can use it like Exchange and it works almost identically. It has an AWESOME web mail interface that gives you calendar/contact/to-to’s with built in spam and antivirus filtering at the server. BUT…
Apple Mail does not support MAPI. IMAP will show the folders for the public contacts and everythign else, but they are in a format that is basically unusable to most people, and even though I can see the calendar events and such, they show up as mail with attachments which, when you click on them import just that event or to-do into iCal. Not usable.
So DITTO on can-we-get-MAPI-in-Apple Mail-PLEASE?
January 22nd, 2007 at 9:08 am
For the love of God,
I can’t believe an actual entourage developer posted here and nobody mentioned category support. This is the single greatest oversight in Entourage and the gigantic limiting factor in its functionality.
CATEGORIES SYNCING ACROSS WIN/MAC PLATFORMS AND YOU’VE ACTUALLY DONE SOMETHING.
I hope you read this ANDY RUFF. This has been a MASSIVE oversight for multi-platform users and syncers.
Thanks,
Ray Born, President
ImPressure-Clean, Inc.
http://www.impressureclean.com
July 19th, 2007 at 2:41 am
I have been using Entourage and recently purchased a Blackberry. Entourage is supposed to support iSync, but it has to sync to Apple Mail and iCal to get to my Blackberry. I have NEVER gotten this to work.
I am getting Exchange mail in Entourage and on my Blackberry from outside the firewall. Both allow me to use the Exchange web mail service. I **dearly** wish that Apple Mail would support this communication scheme.
Bill
December 9th, 2007 at 4:49 pm
Simply put:
- Make Search as good as mail.app with Spotlight.
- Intel Macs
The only reason I keep mail.app around is its incredible search speed and ease of use sifting through 4 gigs of offline mail. Even on my PC side with a large PST/Vista, I miss mail.app for this reason. They really have searching nailed at Apple but using mail.app in imap mode with exchange 2007 has hangs, slow quit, and limitations of collab apps integration (no calendar or address book) And the sync services feature is nice but a bit buggy merging data with iphones, mac apps, and entourage.
Bob