Mac Mail Client on MS Exchange Mail Server?

[The Dude]

Been trying to setup some Macs (Leopard) to use the built-in Mail client application to communicate with our mail server at the office (MS Exchange) with no joy so far.

I read a few online comments about IMAP being busted on the latest Mac Mail. Anyone had any experience or success?

[jamieboy]

I've only set up one Leopard machine, and I've not had any problems. I don't remember that I had to do anything special to set it up, either.

It says it's Mail 3.1 (914/915) and it's connecting to an Exchange 2003 SP2 box.

[CommanderJameson]

Dunno about the Exchange side of things but I think that the IMAP in Mail 3 is better than before; now, it keeps an accurate count of unread messages, and seems to generally behave better and more responsively.

However I should probably point out that my IMAP system is Mail 3 running against the Courier IMAP server on my Linux server; I cannot say whether the IMAP connection offered by Exchange Server is better, worse or the same than the Courier server.

[m12_nathan]

Just install entourage.

[The Dude]

Hmmm. We're running MS ESMTP Mail 6.0.3790.1830.

IF you examine the output on the connection doctor pane on the Mail app, it seems to be trying to negotiate a connection but then just sits there, the result being a "server refused the connection" error.

I'm getting the IT chaps to check if anything gets thrown up in the logs at the server end. They're struggling a little as this is the first time we've tried to integrate the Macs into the system.

What's wierd though is that you can change practically all the server settings in the account on Mac Mail and it doesn't seem to affect the result - like it's failing at the most basic level.

[The Dude]

m12_nathan said:

Just install entourage.

That does seem to be a common solution but if that's the case we could just run Outlook in a VM (already done it and it works) but that's not a very elegant fix.

[cyberface]

Been using Mac Mail over IMAP for years, no problems I can remember. The IMAP server is the OS X Server one though (cyrus) - though I'm using multiple clients connecting to the same mailbox (office workstation, roaming laptop, iPhone, previously a Treo using Chattermail, and an Eee running Thunderbird).

Not seen any problems with IMAP and I run IMAP over SSL.

If your Exchange Server requires secure IMAP then you'll need to get the public key on your Mac and add it to the right place on the keychain - this was always broken in Tiger and needed a hacky fix, but in Leopard Mail, when you first connect you're given the option to permanently accept the key. This *should* work.

However it's a lot more likely to be due to MS's implementation of IMAP in Exchange - I've never heard of anyone having trouble with Linux or OS X IMAP servers, but getting Mail working with Exchange is normally a constant topic of discussion on the technical Mac forums... apparently using Mail as an IMAP client (don't even think about attempting Exchange client) does work shoddily but you do have to turn off publishing public folders to IMAP clients on the Exchange server.

[The Dude]

cyberface said:

Been using Mac Mail over IMAP for years, no problems I can remember. The IMAP server is the OS X Server one though (cyrus) - though I'm using multiple clients connecting to the same mailbox (office workstation, roaming laptop, iPhone, previously a Treo using Chattermail, and an Eee running Thunderbird).

Not seen any problems with IMAP and I run IMAP over SSL.

If your Exchange Server requires secure IMAP then you'll need to get the public key on your Mac and add it to the right place on the keychain - this was always broken in Tiger and needed a hacky fix, but in Leopard Mail, when you first connect you're given the option to permanently accept the key. This *should* work.

However it's a lot more likely to be due to MS's implementation of IMAP in Exchange - I've never heard of anyone having trouble with Linux or OS X IMAP servers, but getting Mail working with Exchange is normally a constant topic of discussion on the technical Mac forums... apparently using Mail as an IMAP client (don't even think about attempting Exchange client) does work shoddily but you do have to turn off publishing public folders to IMAP clients on the Exchange server.

Any idea if the client account should be "IMAP" or "Exchange" then?

Selecting "Exchange" gets you a bit further along the process but neither actually work...

[cyberface]

The Dude said:

cyberface said:

Been using Mac Mail over IMAP for years, no problems I can remember. The IMAP server is the OS X Server one though (cyrus) - though I'm using multiple clients connecting to the same mailbox (office workstation, roaming laptop, iPhone, previously a Treo using Chattermail, and an Eee running Thunderbird).

Not seen any problems with IMAP and I run IMAP over SSL.

If your Exchange Server requires secure IMAP then you'll need to get the public key on your Mac and add it to the right place on the keychain - this was always broken in Tiger and needed a hacky fix, but in Leopard Mail, when you first connect you're given the option to permanently accept the key. This *should* work.

However it's a lot more likely to be due to MS's implementation of IMAP in Exchange - I've never heard of anyone having trouble with Linux or OS X IMAP servers, but getting Mail working with Exchange is normally a constant topic of discussion on the technical Mac forums... apparently using Mail as an IMAP client (don't even think about attempting Exchange client) does work shoddily but you do have to turn off publishing public folders to IMAP clients on the Exchange server.

Any idea if the client account should be "IMAP" or "Exchange" then?

Selecting "Exchange" gets you a bit further along the process but neither actually work...

Don't use 'Exchange' as I've not heard of anyone in the real world using it successfully. Use IMAP and make sure your Exchange server guys support IMAP properly. If they haven't got IMAP working at the server end, your Macs are out of luck. They should be running IMAP over SSL which is port 993 IIRC so ensure that they're aware of this and not using some non-standard port, otherwise your Macs will be talking to a wall.

ETA: your Exchange server guys need to be running OWA as well, since Mail.app uses both IMAP and Outlook Web Access to access Exchange mail.

Edited by cyberface on Monday 17th December 17:05

[jamieboy]

cyberface said:

The Dude said:

Any idea if the client account should be "IMAP" or "Exchange" then?

Selecting "Exchange" gets you a bit further along the process but neither actually work...

Don't use 'Exchange' as I've not heard of anyone in the real world using it successfully.

I'm not a heavy Mac user, but I'm using 'Exchange' and it's working fine in my real world. Like I say I don't use it much, but it works fine when I do. I've no experience of how well it works under stress, happy to take cyberface's word for it, but in terms of a single user connecting it definitely does work.

I've now got it into my head that there was something odd about configuring it initially, so I've just deleted and re-created my account, and it all went along as you'd expect. It took ages to validate the user credentials, but eventually worked. Maybe there was something I did the first time that it has remembered, regarding connecting to an Exchange box?

edit - actually, forget that last bit. The thing that was odd was getting my iPhone to connect to the Exchange box, where the 'Exchange' client type didn't work so it's using IMAP.

So, on my MBP - Leopard, Mail 3.1 configured to use an 'Exchange' type account, Exchange 6.5.7638.1, working with no problems and no tricks to get it set up. I know it's not much help, but at least it confirms that it does work. Unless there's something subtle in the different versions of Exchange.

Edited by jamieboy on Monday 17th December 17:28

[The Dude]

cyberface said:

The Dude said:

cyberface said:

Been using Mac Mail over IMAP for years, no problems I can remember. The IMAP server is the OS X Server one though (cyrus) - though I'm using multiple clients connecting to the same mailbox (office workstation, roaming laptop, iPhone, previously a Treo using Chattermail, and an Eee running Thunderbird).

Not seen any problems with IMAP and I run IMAP over SSL.

If your Exchange Server requires secure IMAP then you'll need to get the public key on your Mac and add it to the right place on the keychain - this was always broken in Tiger and needed a hacky fix, but in Leopard Mail, when you first connect you're given the option to permanently accept the key. This *should* work.

However it's a lot more likely to be due to MS's implementation of IMAP in Exchange - I've never heard of anyone having trouble with Linux or OS X IMAP servers, but getting Mail working with Exchange is normally a constant topic of discussion on the technical Mac forums... apparently using Mail as an IMAP client (don't even think about attempting Exchange client) does work shoddily but you do have to turn off publishing public folders to IMAP clients on the Exchange server.

Any idea if the client account should be "IMAP" or "Exchange" then?

Selecting "Exchange" gets you a bit further along the process but neither actually work...

Don't use 'Exchange' as I've not heard of anyone in the real world using it successfully. Use IMAP and make sure your Exchange server guys support IMAP properly. If they haven't got IMAP working at the server end, your Macs are out of luck. They should be running IMAP over SSL which is port 993 IIRC so ensure that they're aware of this and not using some non-standard port, otherwise your Macs will be talking to a wall.

ETA: your Exchange server guys need to be running OWA as well, since Mail.app uses both IMAP and Outlook Web Access to access Exchange mail.

Edited by cyberface on Monday 17th December 17:05

The server is definitely cofigured for OWA as that's what I normally use to read my mail from home. When setting up the Mail client, should the server be the http address of the OWA server, if as you say Mail IMAP uses OWA? At the minute I'm using the local exchange address (the Macs are located in the office on the network, not trying to access remotely).

[cyberface]

Well if Jamieboy's using it OK in Leopard then it must be a config issue with your Exchange server. I'm pretty sure Apple don't have access to Microsoft's specs for native Exchange communication so they're using OWA behind the scenes.

That said, if you're using IMAP and the Exchange server is set up to support IMAP then it should 'just work' - the address you'll need is the internal address for the Exchange Server. If you haven't got DNS working properly at your site for the Macs then find out the IP address of the exchange server and put that in there. If you're trying to use a windows name then your Macs will have to be integrated into active directory first otherwise it won't know where you're trying to find it.

[The Dude]

cyberface said:

Well if Jamieboy's using it OK in Leopard then it must be a config issue with your Exchange server. I'm pretty sure Apple don't have access to Microsoft's specs for native Exchange communication so they're using OWA behind the scenes.

I'm pretty sure you're right - our IT dept "don't do Macs"... *sigh*

cyberface said:

That said, if you're using IMAP and the Exchange server is set up to support IMAP then it should 'just work' - the address you'll need is the internal address for the Exchange Server. If you haven't got DNS working properly at your site for the Macs then find out the IP address of the exchange server and put that in there. If you're trying to use a windows name then your Macs will have to be integrated into active directory first otherwise it won't know where you're trying to find it.

I wonder if it is as simple as the active directory. I'll poke that tomorrow.