Using Entourage and Mail with an Exchange Server
Volume Number: 20 (2004)
Issue Number: 12
Column Tag: Programming
Using Entourage and Mail with an Exchange Server
by Mark Underwood
Making lots of headway in the "mixed" IT world
While most people think that the best thing for the Mac was the return of Mr. Jobs, quite a bit
of the people in the Corporate IT departments feel it was Microsoft's introduction of Exchange
Server support in Office X and 2004. Not only did it mean conventional corporate users could access
their email, shared calendars, Public folders directly from the server...it also meant they would be
frowned upon less by their support gurus! In this article, we'll give the detailed instructions for
those users and support staffers who want to get or provide direct Exchange services for Mac OS
Versions, History, Requirements And Caveats
First off, remember that this integration process is a moving target for two reasons - both of
them in Redmond. Microsoft is always improving on the abilities of their Exchange Server (we're now
at Exchange Server 2003) and Office (Window's version is 2003 and Mac's version is 2004). While the
protocols behind how an Exchange server talks to the clients that can use it hasn't changed much in
the last four years, Microsoft only started this integration on the Mac side in the last two
In this article, we'll refer to the three Microsoft-supported versions of Office for Mac as
- 2001 - Office 2001 for Macintosh, which only runs under Mac OS 9 (not classic), and is the
equivalent of Office 2000 for Windows
- X - Office X for Macintosh, which is the equivalent of
Office 2002/XP for Windows
- 2004 - Office 2004 for Macintosh , which is the equivalent of Office
2003 for Windows
By "equivalent", we mean that not only are the file formats the same between sides, but with some
very minor exceptions, the same named programs are functionally equivalent. Word is Word, Excel is
Excel, and PowerPoint is PowerPoint. The "minor" exceptions in these named programs mean that
Mac-specific nifties were added above and beyond (not instead of or replacing) the Windows-side
program. Mostly this is in QuickTime, as you might guess.
Before 2001 was released, Microsoft had created a stab at a Mac-based Office quite that had Word,
Excel, and PowerPoint only. They also created a reasonable Exchange client that, oddly enough, was
named "Outlook". This program could fetch mail from an Exchange server and see some of the shared
folders - but only if extensions to the Exchange server was configured - things not turned on by
default when the server is installed. There was another stab at the Outlook equivalent, named
(again, oddly enough) Outlook 2001 that was more stable, yet still not quite the Windows-side. If
the IMAP or Outlook Web Access service is installed, then just about any email client can access
mail - so other than it "looked" more like the windows Outlook, it didn't get any closer to being
With 2001, Microsoft dropped Outlook Express support on the Mac and introduced Entourage. Very
Mac-like, very useful...but not Outlook. Two years later, just after Mac OS X started hitting the
streets, X comes out. Still Mac-like, still useful...and some better Exchange support is integrated -
but the IMAP gateway is still required on the server-end. Now we have 2004, and at last, it's
But Apple wasn't asleep, either. The original Mail program in 10.0 was pretty much just sendmail
on GUI steroids. No Exchange access except with the Outlook Web Access (OWA) gateway. Cheetah
spiffed it slightly - still nothing but OWA. Jaguar added the heavy-duty filters and rules...still
nothing but OWA. It took until the Panther entered the IT jungle for apple to add basic Exchange
service support to their Mail program. We can expect that support to improve with both vendors'
products in their next iteration.
Here's what you need to get this working properly:
Microsoft Exchange Server 2003 or later
Like all things It, the more up to date, the better. Exchange 5.5, even with the POP gateway,
can only provide the mail to any Mac-based client. Exchange 2000 with SP 2 or later can provide
mail, public folders, and calendaring - the basics of dealing with Exchange from the windows-user
perspective. The latest version of server even allows full Active Directory integration for
Exchange (as well as Mail), so that a client Mac isn't any different in usage from a Windows
Apple Mac OS X 10.3
Panther is best for this, on a lot of little levels and one big one. The Windows-integration
inside this version is very clean and works without flinching. We'll give you the details of how to
get that properly set up (as you don't usually think to do it, even in a "mixed" network). It can
be done under Jaguar...but you haven't upgraded yet? Shame on you!
Microsoft Office 2004 for Macintosh
To get the best of Exchange, we highly recommend Entourage 2004, as Apple didn't get the iCal
program to work with Exchange (yet). While Address Book can work with Exchange (through the LDAP
gateway) and Mail with Exchange, if you must use, delegate, and share calendaring, Entourage 2004 is
it. We'll show you how to use Mail and Address book, but seriously consider Entourage.
As with everything Microsoft-related, your mileage may vary. A full list of what does and
doesn't work of the Exchange services and the Mac-based clients can be found on their Mactopia site
This isn't a copy of WinTech magazine, so we won't bore you with the Exchange Server installation
and configuration verbosity. However, we can tell you (and should, as Microsoft's support site
doesn't have all of this together) what services should be activated to make this approach work for
any Mac-based, Exchange compatible client.
Outlook Web Access (or HTTP DAV as it is now know) should be already on, since that's the default
in order to get Exchange email through a web browser. But double-check, and if it uses a different
port than 80, note that down.
IMAP should be turned on, as this is what Apple's Mail program accesses the Exchange server with.
IMAP is a normal method, too...but isn't on by default in some Exchange versions.
LDAP should be turned on. It will be on if you are using 2003, or have your 2000 server
integrated with Active Directory, but again, double-check, and note the port if different than
Configuring Mac OS X
With the server ready to go, let's turn our attentions to the Mac. And yes, before we configure
the Exchange client, we first configure the Mac to act more like it's a PC, with respect to
On a Mac, windows-based services are known under the UNIX parlance name of SMB. Go into your
Applications folder, then down to the Utilities folder, and start up Directory Access.
Figure 1 - Directory
Figure 1 shows up. You may need to unlock access to the settings by authenticating - cick the
lock in the lower left if needed. Once it's available, check the SMB box, select it once, and click
on the Configure button.
Figure 2 - SMB WINS
Windows environments have two major types of authentication: WINS and Active Directory. What
you want to do is to ensure reference from the Exchange server through its background
authentication, as well as how the Mac will (in turn) reference to the server. If you're not the IT
staffer, consult one to find out which applies...using the simple question of "are we using Active
Directory?" Be warned; if you're not the IT staffer, for you to ask such a "geeky" question will
astound them - since it's Microsoft-speak. But if answered "no", you use WINS. If answered "yes",
you can use WINS and Active Directory...or just Active Directory, if the WINS protocol isn't used at
In either case, you can (and should) specify the Workgroup the Mac is living in, with respect to
the other windows machines in your local area. In our example, we have one named "KAUi". But Mac
OS X is also savvy enough to help you see which one you're in...pull down the menu at the end of the
Workgroup field and you'll see all of the workgroups within your LAN or IP sub-domain. Usually the
name of the workgroup is known and called something like your department or company's name. If WINS
is being used, it normally means you're using Windows NT Server and Exchange 5.5. Look at Figure 2,
which is what you'll get when you clicked on "Configure" for SMB. Put the WINS Server's name in the
next field. If you're not using WINS, leave it blank. Click "OK" to take these settings, and we'll
Figure 3 - Active
If you got back "yes" from your question on Active Directory, check it in the Directory Access
dialog, then select it and click "Configure". You'll see a shorter version of Figure 3...extend it by
clicking on the triangle next to Show Advanced Options. What to fill in here depends on the way
your location's Active Directory was set up, so you can safely take these names to your IT staffers
and get what to put in them. Usually only the top three are needed, unless there are more than one
AD in the place.
Once you have those answers to fill in, you will need to click on "Bind..." to add the Mac to the
Active Directory list of clients. This will throw up a prompt to log in with as an administrator,
so you'd better have one handy.
Restart the Mac once both of these are configured to re-register the computer in everything that
matters for the rest of the steps.
Now we turn to creating the Exchange accounts in the two mail programs. We'll do Entourage
Configuring Entourage 2004
Open Entourage 2004, select Accounts from the Tools menu, and then pull down the "New" menu in
the dialog and pick "Exchange..." This starts the Account Setup Assistant, which will try and
automatically detect your Exchange server settings if you provide the basics: User ID, Domain, and
Password. If they're all correct...and you don't have oddities on the Exchange server with respect to
security and such, it will breeze on through and set up your account.
Due to the known and unknown security errors and problems with Exchange, however, most servers
will not be so easy. Let's switch instead to the "Configure account manually" button back at the
start (if the auto-assistant failed in any way to set the account up) and review the settings.
Figure 4 - Entourage
Exchange Account Settings Tab
On this tab, give your account a name, and put in the basics of the server and network. In our
example, we used a domain name of "KAUi" to match the Workgroup name for a 5.5/2000 Exchange server
without Active Directory. If you use Active Directory, you would put in the fully qualified domain
name of the Exchange server. For the name of the server itself, we've used the IP address instead
of the short local name for two reasons: speed and speed. Using the short name means an address
lookup to get the IP address. Multiply that times the number of end users, and you might get a
delay long enough to match the timeout value and get nothing. If the Exchange server speaks to the
outside world (which it should), then it has a fixed IP address and you should use that. Name and
E-mail address are what you want Entourage to show to the outside world through your sent
Now let's look at the Mail tab.
Figure 5 - Entourage
Exchange Account Mail Tab
Critical setting here is how to fetch the messages from the server. We chose "Receive complete
messages" to make sure we can go offline and still read them. Exchange is similar to a standard
IMAP server that leaves messages on itself to retrieve and read. But most folks deal with how POP
servers work...messages get transferred down to the client and not left on the server. So if you saw
the message headers on the Exchange server and then left work, you wouldn't be able to select and
read them without going on-line to complete the process. If you have a slow dial-up situation, you
can check the "Partially receive..." option to cut down on the traffic and set a limit as to the size
fetched. Message Options for signature and header information go here on this tab. Let's move on
to the Directory tab.
Part of the beauty of the Exchange server is centralized services, such as a single corporate
address book, shared folders, and shared calendaring. On this tab, we deal with the Address Book
part. If your IT staffers have set up the Exchange server with the LDAP extension, put either the
name or IP address of it into this field. Name's okay here, as the lookup's different. With LDAP,
there was also a search base established for how broad of a group is examined when accessed...normally
"dc=local" will do, but check your settings. Trimming the number of returned names speeds things
up, and I'm sure you don't have 100 John Smiths in your company, anyway. Figure 6 shows our example
Figure 6 - Entourage
Exchange Directory Services Tab
Next is the Advanced tab, where the spiffy Exchange services get set.
Figure 7 - Entourage
Exchange Advanced Tab
Normally, the same Exchange server is mail, calendar, public folders, and directory. We again
used the fixed IP here to cut down on response time. Synchronization is best done always, hence
that as the default setting. You have the option to pick a specific category within Entourage to
synch, or to synch all but a specific category (such as a person category), or not to synch at all.
This synch applies to everything - calendar, address book, tasks, etc. If you don't want your
private life spilling into the corporate Exchange server, you don't use the same account in
Entourage to do both types of mail - simply said. On to the next tab.
Delegate is an option within Exchange to allow others of your choosing to act as a 'delegate'
with respect to your calendar and tasks information. Administrative assistants, for example, or
co-workers on a project. You normally delegate with settings back at the server-end for starters,
but within Entourage, you can refine the settings to specific individuals and responsibilities.
Figure 8 - Entourage
Exchange Delegate Tab
Listed here will be the ones your Exchange server has listed for you already, and you can add
others within the guidelines and roles set up there. In our example, we didn't do any delegation,
as its best to test that later. On to the Security tab.
Figure 9 - Entourage
Exchange Security Tab
Digital certificates are often allowed in Exchange servers, as Windows server have the option to
generating them for use by clients. Here is where you indicate which one(s) to use for both signing
This completes the configuration for Entourage 2004...now you can close the edit by clicking the
"OK". Entourage will find the Exchange server, and voila! You should see your left column look
something like this:
Figure 10 - Exchange
Server Folders in Entourage
Configuring Apple Mail
If you use - or what to use - Apple's Mail program to access the Exchange server, the steps are a
little easier due to the fact that Apple's Mail program relies on the IMAP, LDAP, and WebDAV
extensions to the server, instead of the Windows-based default services.
Open Mail, bring up the Preferences, click on Accounts, and create a new mail account to start
the process with.
Figure 11 - Setting up
an Exchange account in Apple Mail
Pick "Exchange" from account type, provide a description for the account, then put the email
address and name you want associated with the account from the outside world's perspective.
Incoming server is the Exchange server - notice that we again used the fixed IP to save speed - and
user name/password are those of the server's.
Our outgoing server relies back on the ISP's, since we're not really using the full Exchange
suite here. Recall that many ISPs prevent you from relaying messages, so you normally use the same
as any outbound POP account(s) you may have.
The last entry here is the Outlook Web Access Server, should your Exchange server be a pre-2003
version. Mail will switch to using its gateway, rather than the IMAP.
Done! Apple's Mail has been configured for Exchange. Now we turn to the Address Book approach
for getting that shared resource to work with Mail.
Configuring Apple's Address Book
Since Address Book is used for many programs under Apple's default suite, it may be nice to add
it anyway - even if you use Entourage. Open Address Book, go under its Preferences, click on the
LDAP tab, and then the plus sign at the bottom to add a new directory server.
Figure 12 - Exchange
through LDAP in Address Book
As we did in Entourage, LDAP settings are the same for Address Book. Server name or fixed IP
address, search base, etc. are all the same. Add it, then click on "Save" to save it.
To use the LDAP, exit the Preferences, go to the top of the first list on the lft and click on
the icon labeled "Directories". Next to it should now show up your Exchange server via LDAP. Click
on it to restrict searches to it, and then type in a name or location in the search field at the top
right of the dialog, then press return. Any results will be listed in the bottom pane. Voila!
Well, whether you went the all-Apple or all-Microsoft approach to adding Exchange
services to your Mac - or to the Macs you support if you're an IT staffer - you see that it's much
easier than it was just a couple of years ago...and it can only get better as time goes on. We hear
rumors of abilities being added to Tiger's versions of Mail and Address Book, as well as more
surprises from Redmond in the next wave of Exchange. But this advancement makes it a lot easier for
the "mixed" world to let both cats and dogs eat at the same diner indefinitely. ?
While it's not a perfect fit - there are some Exchange services still only for Windows-based
clients, but they are nominally not the day-to-day sorts of things - the benefits of migration in
either direction by introducing this compatible approach far outweigh the 'single platform' mantra
folks have had to hear for decades. Let's all hope the tide has indeed turned, and the folks at
both locations keep this alive and flourishing.
Mark Underwood was born in Lexington, Kentucky and started writing not too long
after that event, cutting his first set of teeth on Robert Heinlein and J.R.R. Tolkien. He
currently lives near the Atlanta area with his family, three cats, and close to two dozen computers
that are currently combined in solving the children's homework and the amazing mysteries of the IT