Connecting an iMac to an SBS 2008 server

Hi, I have been attempting to help a client with one iMac running os X 10.9.4 connect to an SBS 2008 server for two user accounts connecting to one shared folder and for domain emails.

It's a bit hit and miss so far and emails reach the SBS server and report 041 under message info, but aren't delivered.

One problem seems to be it looking for an old SSL, remote.mystuff.com which has been replaced on the server by mail.mystuff.com and I can't remove or change this.

Thanks for any advice anyone can offer.
bill2013Asked:
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Cris HannaCommented:
I'm by no means a Mac Guy, but I am an SBS guy.  
So how are they attempting to get the emails?  Using Outlook for Mac?  OWA?
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bill2013Author Commented:
Same with me Cris. They are using Mac Mail.
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Cris HannaCommented:
I don't have any experience with MacMail.  But I'm going to copy from a book called SBS 2008 Unleashed (http://www.amazon.com/Windows-Small-Business-Server-Unleashed/dp/0672329573)  Eriq was an SBS MVP and a Mac guru.  "Next to shared file access, user access to e-mail is the most requested SBS resource from the Mac user. Unfortunately, there are not any native Macintosh tools that interface effectively with Exchange, so Mac users wanting to gain the full benefit of Exchange have to use Outlook Web Access or Entourage. "   Eriq addressed a whole chapter to connecting Mac's to SBS 2008...I'd encourage you to get the book.   In full disclosure, I am a co-author but did not contribute to the Mac Chapter and receive no royalties from the sale of the book.

That said, if you really want to use Mac Mail you can look at this article http://blogs.technet.com/b/sbs/archive/2008/09/19/how-to-configure-sbs-2008-to-host-pop3-imap4.aspx    I don't recommend this as you risk becoming an open relay.
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serialbandCommented:
You might just need to go to the Mac Mail Preferences and change the Outgoing Mail Server.
  Click on Mail then Preferences or just press Command+, (that's a comma) to get preferences.
  Click Accounts.
  Under the Accounts tab, look for Outgoing Mail Server (SMTP) and select Edit SMTP server list
  click on + to add your server
  click on - to remove the old server.
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bill2013Author Commented:
Thanks Cris, I have THAT book!! and didn't think to look there. Will check it out tomorrow when I have a remote connection to the iMac as well as testing serialband's suggestion, but pretty sure we came across an error doing this. Will report back when tried.
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bill2013Author Commented:
Sorry guys, I thought I had confirmed your suggestions or a mish mash of them worked, ages ago. With your help on the mail settings and a few ideas from the book everything is working fine now.
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