More on Entourage Vs Mail.app
Jesse Hollington saw a recent post on Hawk Wings about how Mail.app bests Entourage and emailed me a thoughtful account of his own experiences. It’s good enough to share.
I’m an IT Consultant with a good number of years in the business of e-mail systems specifically, and of course am saddled with Exchange on the back-end for my corporate mail for various reasons, the most notable being Blackberry integration.
I’m also a “switcher” having liked the Mac for some time, but having been afraid that it wouldn’t quite do what I needed it to do (with groupware access being high on the list — I saw “groupware” rather than “e-mail” because we’re talking calendars, tasks, and all of the other myriad items that come with doing business). The availability of Entourage and its integration with Exchange was a huge selling point for switching to a Mac last year.
Although I started on Entourage, however, I’ve been back and forth between Entourage and the iApps about three or four times, but think I’ve finally settled back down on the iApps.
The biggest thing that threw me off of Entourage originally was the lack of sync services integration. Everything else on my Mac wants to talk to the address book and calendar. The lack of any kind of decent searching options was another. This would have been around last November that I decided to shut down Entourage and switch back to a combination of Mail.app, iCal, and Address Book. I went away from a Blackberry around the same time, and got an iSync-compatible phone.
When they fixed that in the service pack last March I happily went back to Entourage, since shared calendars and tighter Exchange integration were desirable, and it seemed that Spotlight and Sync Services integration could finally deliver the best of both worlds.
However, Entourage still felt “clunky” compared to the pleasant user experience of using Mail.app, and I wrestled with the decision more than a few times. The final deal-breaker, however, came when I was searching for something that would have been in one of my attachments and came to the realization that Entourage, despite its Spotlight integration, does not do full-text searching of attachments (Mail.app does). The result was that it took me about four times longer to find the mail item I was looking for. Within 24 hours after that I had moved everything back to Mail.app.
The truth is that for Exchange integration, the iApps are not without their options — options that have expanded since my first foray into them a year ago….
- Naturally, Mail.app will talk IMAP, so as long as those ports are open on your corporate firewall, this works just fine.
- Exchange Public Folders can even be exposed via IMAP, and in some ways work better than Entourage (there is no support for free-standing documents, or ‘FreeDocs’ in public folders in Entourage — they simply do not appear. Via IMAP, they will at least appear as attachments to blank e-mail messages). Obviously shared calendar and address book folders from Exchange won’t be represented properly in Mail.app, but you will see them as IMAP folders with each entry as a mail-type message.
- OS X’s built-in Address Book will sync to Exchange quite well, subject to the configuration of Outlook Web Access on the Exchange side (there are a couple of little idiosyncrasies on how Exchange needs to be configured to support this, although it would be fine “out of the box”) Only primary contacts can be synced of course, so any shared address book “public folders” are definitely out here, unfortunately.
- Snerdware’s GroupCal can be used to synchronize selected iCal calendars with the Exchange calendar. It has improved dramatically in the past six months. When I first tried it last November it was still in beta as far as Tiger support was concerned, and even after release it took until version 3.5 until it was ready for prime time. Shared calendars are also supported from public folders, since each calendar can be given a URL.
In addition, GroupCal will handle the synchronization of tasks to the Exchange server — something that even Entourage inexplicably doesn’t do (Entourage provides local support for tasks, but these are only stored locally). Since I carry a Blackberry and get my tasks synced wirelessly from the Exchange server, the ability to sync those between my desktop and Exchange server is crucial.
The other thing that I found particularly annoying about Entourage was its database. While it’s fair to say that all of the historical problems with database corruption seem to have been resolved (I never had a single issue, even with a 2GB+ database), it’s a nuisance as far as backups are concerned. With Mail.app, my incremental backups end up being much smaller, since only the changed information is coming across. With Entourage, the entire 2Gb database goes into every incremental backup (since it will have generally changed each day). This increases the time that it takes to backup, and of course decreases the number of backups that can be kept (since they’re larger).
To be fair, Entourage does have some features to recommend it, in large part the “Project Centre” and the level of integration that is available between the components (the linking of contacts, tasks, calendar items, and notes to e-mail messages is a nice feature, but much of it can be replicated with the multitude of plug-ins available for Mail.app — I find MailTags 
, quite specifically, addresses most of the features that Mail.app would otherwise be lacking in this area).
The Project Center was also a nice way of looking at things, but again I found it too confining, when generally a Spotlight search combined with proper use of Mailtags can often provide a more comprehensive view of what I’m looking for.
One other significant advantage of Entourage is that it communicates using the norrmal Outlook Web Access protocols (WebDAV, specifically). This means that as long as Outlook Web Access is available, Entourage will work just fine. My wife uses Entourage on her iBook for that very reason — She’s a teacher, and the school board does not provide any access outside their firewall other than OWA, so IMAP clients are definitely out in the cold. Despite this, however, Entourage still communicates with the Exchange server very effectively and allows her to download her mail and use all of the features of Entourage. Mail.app simply can’t go there due to the IMAP ports being blocked.
At any rate, I just thought I would share my experiences as somebody who
has been down the road a few times — in both directions.
Thanks, Jesse. The IT Department where I work would sooner carve their own hearts out with plastic teaspoons than install Microsoft Exchange Server. If things were different, I’d find the tips here especially useful.
Tags: Apple Mail, entourage, exchange server, groupware, mail.app, microsoft, Productivity, switchingRelated posts
September 7th, 2006 at 1:08 am
My experience is much the same though once I switched to Mail there was no turning back.
I understand Microsoft are going to be going the Mail route and are unbundling the address book and calendar from Outlook/Entourage. Wonder why?!
I always felt unsafe with Entourage having its own database with all my data in it. I read of many people who lost everything. I never did but I feel much happier with Mail.
It just works, it feels more efficient, it’s safer, more elegant and after a transition, more productive.
September 7th, 2006 at 2:43 pm
[...] More on Entourage Vs Mail.app I’ve loved the integration of Mail with Address Book, and I’ve never understood why Entourage didn’t use it. (tags: entourage email mail.app business) [...]
September 7th, 2006 at 4:56 pm
Two quick points.
1) Have a look at Crm4Mac.
I just started using this today. The package is smart - it links iCal, Address Book and Apple Mail in a sophisticated manner - perfect for anyone involved in sales etc. You know it is good when the Windows users all around you ask “Is there a PC version?”
If you are in sales, as I am, this product makes the iApps shine!
2) One issue you can have with Apple Mail and Exchange Servers is that Microsoft’s implementation of IMAP ain’t the best. It is possible to drive cpu usage on your server to 100% by either having more than one user on the same machine (fast switching) checking mail at the same time or when users have too many files/folders being synced between their machine and the server. (Get them to keep as much local as possible)
September 7th, 2006 at 9:21 pm
“OS X’s built-in Address Book will sync to Exchange quite well, subject to the configuration of Outlook Web Access on the Exchange side (there are a couple of little idiosyncrasies on how Exchange needs to be configured to support this, although it would be fine “out of the boxâ€)†How can one accomplish this? I’ve tried without success with my company’s Small Business Server 2003. Would appreciate very much your collaboration,
September 7th, 2006 at 11:07 pm
Quirilio,
The short answer is that the OS X Address Book actually communicates with Outlook Web Access (OWA), which is what it uses to sync. It doesn’t support forms-based authentication, which is what most sites in fact *do* configure when setting up SSL, although it is not on by default (hence my comments about it working “out of the box”) Note that OS X is not unique in this area… Microsoft’s own ActiveSync technology has problems with FBA as well.
Forms-Based Authentication is the mode whereby you get nice logon page when logging in to Outlook Web Access (as opposed to simply a browser-based authentication prompt).
There are three ways you can make this work:
1. Turn OFF forms-based authentication entirely. You can then use an SSL connection to your OWA and it should just work.
2. Use a non-SSL connection to your OWA. Forms-based authentication is only used over SSL. Non-SSL connections will not use it, and therefore will work fine. Note that this is *not* recommended if you are accessing OWA from outside your corporate firewall, as it means all of your address book data is travelling across the Internet “in the clear” (non-encrypted). In this case, just use an “http://” URI to your OWA server (ie, http://myexchangeserver.com/exchange).
3. This is much more complex, but if forms-based authentication is desired *and* you need to synchronize your address book over SSL, you could set up a second virtual server in IIS with FBA turned off on that second server. This is a more complex task, obviously, as it involves either a second IP address or a distinct host name to differentiate the two IIS virtual servers. Basically, in this case users accessing OWA would log in to the primary server with FBA turned on, and synchronization would communicate with the secondary one (using a different IP address or DNS name).
September 8th, 2006 at 5:25 am
I use Kerio Mailserver which “fakes” a Exchange server. Kerio is much cheaper than Exchange and it has a great webmail (better/nicer than OWA). The integration of Entourage with Kerio is better than mail.app with Kerio. There is also a Outlook Connector, so the integration Outlook with Kerio is also good. Just download it from Kerio.com and you will be surprised.
A great solution: Kerio on a XServe and Entourage on the OSX-clients and Outlook on the Win-clients. For the web-workers the webmail.
September 8th, 2006 at 12:03 pm
Thanks, but we do use Windows Small Business Server. I would appreciate someone that can help me configure the Exchange Server in order to accept the Address Book Sync.
September 8th, 2006 at 6:00 pm
The manual from Kerio is maybe useful. You can download it from their site. In the manual is a chapter about configuring Addressbook/iSync with Kerio (or Exchange). There are also chapters about Entourage (vX/2004), iCal en Mail.app
September 8th, 2006 at 9:18 pm
I’m really surprised about this “Entourage, despite its Spotlight integration, does not do full-text searching of attachments (Mail.app does).” I experimented with this a while ago, and found that attachments are not scanned by spotlight.
To test, I created a pdf using pages with some crazy string, and searched for the string using spotlight. It was found. I then put it as an attachment in an email message and erased the original. I then searched for the string and could not find it.
Did I miss something in my tests?
September 9th, 2006 at 5:34 am
Quirillo: I posted a reply in the comments above, but it seems to be “awaiting moderation” so I’m not sure if you can see it.
Alan: I haven’t tested this specifically with a PDF file, so it’s possible these aren’t indexed by spotlight properly. However, I know that Word/Excel documents, text attachments, and Pages documents are all indexed by Spotlight in Mail.app, but *not* in Entourage. This is basically because Spotlight doesn’t index Entourage’s database content directly, but rather only metadata that is specifically exposed by Entourage, and attachments are not exposed this way.
September 11th, 2006 at 4:50 am
Jesse: this is intereresting to know. I had decided against a Mail.app storage of documents because of this, but I’ll need to check more thoroughly which file types are indexed and which are not.
September 11th, 2006 at 8:22 am
Thank you all. Jesse, pardon my ignorance, but how can I implement option number two with mail.app., do I have to configure something on the windows exchange server side? or just my mac?
September 16th, 2006 at 1:57 am
Alan: After a bit more specific testing on my own, it seems I spoke too soon….
Mail.app does full-text index everything it can in an attachment, so text attachments are definitely included (in my case, I do get a lot of text attachments in the form of scripts and so forth, so it’s very useful to me). Entourage definitely does NOT present this information to Spotlight, since the metadata is creates does not include attachment data, even for text attachments.
The problem with attachments other than text files is that they are base-64 encoded, and at this time Spotlight doesn’t do any base-64 decodes when building it’s index.
In my case, the fact that I had many of my attachments already living in my Mail Downloads directory did allow Spotlight to find them, but at files that had been saved to my hard drive.
I don’t imagine that it would be an overly complex thing for an experienced programmer to write a Spotlight plug-in that would search the base-64 encoded portion of Mail.app messages, but it doesn’t appear to have been done by anybody yet.
Quirilio: The configuration is actually done in the Address Book app. You go into preferences, and select “Sync With Exchange” and then provide the particulars to your Exchange server, including the path to WebAccess, using an http:// URL.
Whether or not option two above works for you is dependent upon the Exchange server configuration and your firewall configuration (at the Exchange server). Some organizations block port 80 to the Exchange server to force their users to use SSL (HTTPS) connections.
The simplest way to test this is to fire up your web browser and see if you can get at Outlook Web Access using an http:// url (as opposed to https).
September 19th, 2006 at 3:42 pm
Jesse: it would indeed be great for someone to write such a plugin. I don’t know how difficult it would be though: one would need to somehow integrate with Mail.app (which does not seem to nicely expose its api), decode the base64 attachments (easy), and push everything back to Spotlight so that the right importer for the attachment is used.
I guess this is just one extra feature to add to a “perfect mail client” that I hope someone will write one day ;-)
September 22nd, 2006 at 10:04 pm
This is a little harder than you may think. remember most attachments would not be clear text — so just base64 decoding them would not be enough because then you would more or less have to pipe the attachment though the mdimporter of whatever filetype it may be (word, excel, omni outliner, whatever) and then somehow associate that back to the email message.
One thing that may be possible is to add a metadata field “mailMessageAttachment” = “messageId” that would point back to the source message — and figure out how to return hits (in Mail) for those documents so that it would know to get the original message.
Not to say impossible, but not trivial in the least (and I have grokked a good understanding of Mail’s internals)