Outlook 2011 for Mac will not connect to Exchange

I have a SBS2008 with 5 clients, 3 Windows7 and 2 MacBook Pro's.
Both MacBooks is running OSX 10.6.6 and Outlook 2011.
For some reason the one of the Macbooks will periodically not connect to Exchange.
This is outside LAN as well as inside.
Thawte has issued a valid certificate.

I have placed the two Macbook's side by side and can confirm that settings is matching!
What is wrong here???

Settings in Outlook are as follows:

Exchange Account

Validation: Username and password

Username : DOMAINNAME\LOGIN

Microsoft Exchange:
Server: mail.DOMAIN.dk    : 443
v USE SSL
OhmitAsked:
Who is Participating?
 
Philip ElderTechnical Architect - HA/Compute/StorageCommented:
There should be no reason to point out port : 443 in the Server setting as the "Use SSL" setting enforces communication on that port.

What service pack level is Exchange at in SBS 2008?

Philip
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OhmitAuthor Commented:
Please notice, that the are several clients connected to this SBS so I don't belive the server is the issue.
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Philip ElderTechnical Architect - HA/Compute/StorageCommented:
My reference was to your Outlook settings?

Philip
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OhmitAuthor Commented:
:-) you asked for SP levels of Exchange?
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woolnoirCommented:
What error is produced on the machine that wont connect ?
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Philip ElderTechnical Architect - HA/Compute/StorageCommented:
Yes, there were two parts to the original post:


Settings in Outlook are as follows:

Exchange Account

Validation: Username and password

Username : DOMAINNAME\LOGIN

Microsoft Exchange:
Server: mail.DOMAIN.dk    : 443
v USE SSL

Q 1: Why is the :443 there since the next setting:
v USE SSL
  ... means that 443 is used anyway.

Q 2: What is the service pack level of Exchange? That can impact Outlook on Mac's connectivity.

I will try and get our Mac set up to get a better idea of what is up for the settings.

Philip
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OhmitAuthor Commented:
Hi Philip :-)

The 443 is default settings.
I have two similar MacBooks both with OSX 10.6.6 and Office 2011.
If I compare the settings they match 100%.
Difference is that one of them works the other don't!

I will check SP level of Exchange and get back ASAP

BONUS INFO :-)
If I configure the "good" MacB with the "bad" mac's user credentials it works perfect.
This should indicate without any doubt that the problem is located to the MacBook!
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