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Small Business Server Support Forum    
Subject: Connecting Apple Mail (on OSX 10.5) to Exchange 2003
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Paul Smith User is Offline
Tadley UK
Member since
4/20/2005

Registered Users
Posts: 293

2/16/2008 06:17 PM  
I have a problem getting OSX 10.5 (leopard) to pick up EMail from MS-Exchange 2003 (SBS 2003 Standard R2) - ISA 2004 is NOT installed.
 
I have modified the MAC Network connections and it picks up the Windows Domain correctly, and can resolve my local netbios names etc etc.... I can connect to SBS using RWW from the MAC.
 
The problem comes when I try to configure Mac Mail V3.2 - Their preferred Email Client to pick up email from the server.
 
I defined a MacMail Account, I chose Exchange from the set of 3 (POP, IMAP & Exchange), I entered . for incoming and outgoing email servers. Changed authorisation to be NTLM, and gave it the windows Domain name, entered the Userid and passwords and so on.
 
However when I try to pick up mail it gives me a connectivity error. 'Connection refused to port 143', I also tried secure SSL (port 993) too but I am not convinced that MacMail was using this as it did not seem to 'take' when the MacMail settings were Saved.
 
It suggests to me that the SBS server is not allowing the connection form somewhere.
 
So can anyone tell me the steps required to get a Mac to connect to MS-Exchange please? (Also bear in mind that I dont know much about AppleMacs and am working this out step by step. Windows & SBS I am fine with.)
 
Its possible that I have missed setting up something on SBS too. However I have added Mac file sharing support and enabled AppleMac sharing too, so I think that I have covered that one. It possible that I may need to get the Apple to install the UAM, and import the certificate too, but I am not sure.
 
Any help would be appreciated.
 
Thanks
Paul
Eriq Neale User is Offline
Texas, USA
Member since
5/3/2005

Microsoft MVP
Posts: 2105

2/16/2008 07:23 PM  
Paul - 

Take a look at Chapter 17 of the SBS 2003 Unleashed book for more detail about what I'm sharing here. MacMail does NOT have true Exchange connectivity, even though one of the options for mail server is "Exchange." Mac Mail can only make POP3 or IMAP connections to mail servers, and the Exchange option in MacMail assumes an IMAP connection to the Exchange server.

By default, IMAP and POP3 are not configured in SBS 2003.

You have two options:
1. Enable the IMAP service in Exchange and configure MacMail to use that.
2. Get a copy of Entourage from Office 2004 or Office 2008 and connect to Exchange with that.

Unless the Mac user specifically does NOT want to get to his calendar or contact information in Exchange, I would strongly recommend using Entourage instead of MacMail.

Information about configuring Entourage 2004 to connect to SBS can be found in the SBS 2003 Unleashed book, but can also be found at http://simultaneouspancakes.com/Lessons/2005/01/02/how-to-configure-entourage-2004-for-sbs-2003/, which is actually a little more up to date than the information in the book.

HTH...

-Eriq

Eriq Neale - Small Business Specialist, SBS MVP, Mac Guru
EON Consulting LLC www.eonconsulting.net
Author of Microsoft Small Business Server 2003 Unleashed
Listen to eOnCall at AIRtunZ or visit www.eoncall.com.
Paul Smith User is Offline
Tadley UK
Member since
4/20/2005

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Posts: 293

2/17/2008 10:07 AM  
Eriq,
 
Thanks. I was begining to suspect this, but my lack of Mac knowledge was holding me back there.
 
I presume that from your viewpoint that running Entourage is much more preferable to running IMAP for Exchange? I already have POP3 configured as there are a number of POP3 mailboxes that they want to be able to use as well as MS-Exchange.
 
I will read the info you have pointed me to and have a chat with my Mac client. Its a pain as this is the only thing holding me back putting them onto a full network.
 
Cheers,
 
Paul
Bryan O'Malley User is Offline
United States
Member since
2/29/2008

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Posts: 2

2/29/2008 03:27 AM  
There is something odd with your post that's preventing me from seeing the entire thing, so pardon me if I miss something you've said...
 
I have Mail.app under Leopard working my Exchange under SBS 2003.  It was slightly tricky to setup, but it certainly can be done.
 
You need to make sure that IMAP is running on server.  By default, it's not enabled.  Do a quick Google for enabling IMAP under SBS and you'll get the directions.
 
I also struggled with making sure all the right ports were open on the router and getting the appropriate security for IMAP and SMTP so that only my users could work with the server, not just any bloke that comes along.  It took a bunch of tweaking and trial & error, but I got it working.
 
The good news is that once I had all the settings configured, it works like a charm.
Eriq Neale User is Offline
Texas, USA
Member since
5/3/2005

Microsoft MVP
Posts: 2105

3/10/2008 11:52 PM  
Paul -
 
Yes, I do prefer Entourage with native Exchange communication versus IMAP, even over SSL. I highly prefer IMAP over POP3, but if you can get them running Entourage, that will give them full access to mail, calendar, and contacts, and that won't happen with IMAP.
 
Yes, you can secure IMAP, and we've got articles related to that, but if you've got access to Entourage, have them use that as a first option, if they'll go for it.
 
-Eriq

Eriq Neale - Small Business Specialist, SBS MVP, Mac Guru
EON Consulting LLC www.eonconsulting.net
Author of Microsoft Small Business Server 2003 Unleashed
Listen to eOnCall at AIRtunZ or visit www.eoncall.com.
Paul Smith User is Offline
Tadley UK
Member since
4/20/2005

Registered Users
Posts: 293

3/12/2008 01:43 PM  
Hi all,
Thanks for your help, all very useful suggestions and thoughts. As is teh way of these things, my end-user has decided that he hates Entourage and has setup a new POP3 mailbox and asked me to forward all emails to that mailbox instead .... as well. I think that I will probably sort myself out with a Mac and see if I can get this all working anyway as its bound to crop up again.

All the best

Paul
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Forums > Microsoft Smallbusiness Server > How do I setup my Apple Macintosh on a SBS 2003 ne > Connecting Apple Mail (on OSX 10.5) to Exchange 2003



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