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I have a client with a MacBook Pro running OS X Tiger. The rest of his network is all Microsoft software. I'm having trouble connecting the mail app to the Exchange Server. I've tried with another MacBook Pro and am experiencing the same problems, so it's possible the problem is serverside, or that there's something on the account setup on the mac that I'm getting wrong.

I've checked and doublechecked the credentials and server details, enabled POP on the server and tried to connect via that as well, but still no joy. Can anyone shed any light on this, or recommend some third party software that will sort this out?

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I've never used it with POP, but why not enable IMAP instead? That surely worked for me. For OS X Leopard and earlier be sure NOT to select "Exchange" in Mail, but use IMAP. Up to Snow Leopard, Apple Mail does not support the Calendar and Contacts anyway, so using IMAP works just as well.

According to Mail 3.5 help:

An Exchange account allows you to connect to your Exchange server via IMAP, while Mail filters non-email related content from the server.

So, using "Exchange" requires IMAP to have been enabled on the server. Using "Exchange" in Mail does solve some issues, but at a cost:

  • Microsoft Exchange and Apple Mail use different names for some folders (like Sent Items and Deleted Items for Exchange, and Sent and Trash for Mail). When using "Exchange" rather than IMAP then these name issues are solved automatically.
  • Exchange has some additional folders such as Calendar, Contacts, Journal, RSS Feeds, Sync Issues and Tasks. When using "Exchange" then these odd folders seem to be hidden.
  • The help says "if you enter text in the Outlook Web Access Server field, Mail filters non-email related content from the server". Apart from the aforementioned Calendar and Contacts folder, this also implies that all calendar and contacts information in any other box (such as public folders, your Inbox, etc) will not show up. A good idea in general, but in the Inbox it means you don't get calendar invites, and bounced messages are not normal mail either so you would never know if you have messages that didn't go through. (quote)
  • This might need some more network traffic through the so-called "Outlook Web Access" URL.

When IMAP has been enabled and the IMAP ports have been opened in the firewall, then in OS X Leopard:

  • Menu File, Add Account
    • Account Type: IMAP (not Exchange or POP)
    • Incoming Mail Server: the incoming server of your email provider
    • Outgoing Mail Server: the SMTP server of your email provider. This is especially preferred in case of anti-spam SPF records. But if you cannot use that server (like when you don't know the authentication details, or because your internet provider blocks access to third-party SMTP servers), then use the SMTP server of your own internet provider instead.
    • Use Authentication: yes (even when using the SMTP server of your own internet provider: if you take your notebook on the road, then you're probably not connected to the internet using your own provider, so to use the outgoing mail server of your own provider you'll need to provide some credentials)
  • Mail will now automatically find the preferred (and most secure) settings.

To ensure the trash is not emptied automatically:

  • Preferences, Accounts, tab sheet Mailbox Behaviors
  • Permanently erase deleted messages when: never

To make the Sent, Drafts and Trash work (this would not be needed when using "Exchange" rather than plain IMAP):

  • After setting up IMAP you need to tell Mail which folder on the server is actually to be used as the Trash, Sent items, etcetera. First let Mail download all your messages, which can take some time -- it might even seem that all is done while no folders are visible yet! At some point you'll see all your folders as stored on the server.
    • Select the "Deleted items" folder and choose menu Mailbox, option "Use this mailbox for". Once you've selected the right usage, the server folder will be integrated in Mail's usual interface.
    • Repeat for "Sent Items"
    • Repeat for "Spam mail"

To ensure Windows users see your attachments:

  • Choose menu Edit, Attachments, Always Send Windows-Friendly Attachments
  • Choose menu Edit, Attachments, Always Insert Attachments at End of Message (a bug requires you to first type at least one character in the body when dragging attachments to a message)

Instead of IMAP one could also use fetchExc -- fetches mail with webDAV from MS Exchange 2000/2003 servers (see also How I Quit Fighting The Man). I never tried that, and don't know of any advantages. Snow Leopard is said to support Exchange for Mail, Address Book and iCal (but maybe only as of Exchange 2007), so upgrading may be money well spent.

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Do you get any specific error messages when you try to connect or set up the account?

After googling I found these two articles which handle similar problems:

These articles basically describe problems with header information on apple mail applications in usage with exchange server - but also describe the mac to exchange setup in more details.

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Hi, thank you for your response. The message is simply that 'the Exchange server is not responding' when trying to add an account. I've logged onto OWA using the same credentials, and all other users on the network. IMAP service is not started on the server at the moment, should I try enabling it and connecting with that? – Tristan Aug 20 '09 at 10:06
yes, I would recomment that over OWA - as IMAP allows you to store mails on your pc. – Shaharyar Aug 20 '09 at 10:23

I thought built-in Exchange support wasn't coming until Snow Leopard (10.6)?

I don't use Exchange with my Mac, but I thought the only way to hook into Exchange pre-Snow Leopard is with Microsoft Entourage.

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Support is already there, but just very limited, and needs IMAP to be running on the server anyhow. So, given the limited support in, IMAP on the client is just as good, and needs less fuzzy configuration. When using IMAP, even on Leopard and earlier there's no need to use Entourage (though one would not be able to use the Contacts and Calendar, which Entourage may support). – Arjan Aug 20 '09 at 12:10

As mentioned earlier, your exchange server communicates with the Outlook client through MAPI, or EWS if your exchange server is 2007 or 2010....

But, the Apple Mail client doesn't do MAPI or EWS yet, that's in Snow Leopard, and would require Exchange 2007 or higher to be supported. Apple Mail currently uses WebDAV through the OWA server... So if you do not have WEBDAV enabled on the Exchange server, you'll get no where...

As mentioned earlier using IMAP is a good solution, but I prefer the WebDAV settings myself...

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What's the advantages of WebDAV then? – Arjan Aug 20 '09 at 19:55
Entourage can't see the exchange server if you configure as IMAP, it's just a generic mail server to entourage then. WebDav is depreciated and being eliminated by Microsoft, along with MAPI. Microsoft is moving towards EWS (Exchange Web Services) as the officially supported communications, first supported under Exchange 2007. – Benjamin Schollnick Sep 27 '09 at 23:49

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