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Internal CA do matter, you can install the certificate on the computer you're trying to use outside of the network. I am assuming you are attempting to connect externally, right?
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Internal CA do matter, you can install the certificate on the computer you're trying to use outside of the network. I am assuming you are attempting to connect externally, right?

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No - external connections work fine. The internal ones are not working.
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No - external connections work fine. The internal ones are not working.

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Is SP1 installed for Outlook?
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It allows me to set up the Exchange account via Control Panel | Mail, but when I open Outlook I get this message:<br />
<br />
“Outlook cannot log on. Verify you are connected to the network and are using the proper server and mailbox name. &nbsp;The connection to Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action.”<br />
<br />
We use self-generated certificates for Exchange OWA if that matters.<br />
<br />
Any suggestions?
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</div>


It allows me to set up the Exchange account via Control Panel | Mail, but when I open Outlook I get this message:

“Outlook cannot log on. Verify you are connected to the network and are using the proper server and mailbox name.  The connection to Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action.”

We use self-generated certificates for Exchange OWA if that matters.

Any suggestions?

Outlook 2010 cannot log on to Exchange 2010 Server

Exchange is the server side of a collaborative application product that is part of the Microsoft Server infrastructure. Exchange's major features include email, calendaring, contacts and tasks, support for mobile and web-based access to information, and support for data storage.

Exchange

Microsoft Outlook is a personal information manager from Microsoft, available as a part of the Microsoft Office suite. Although often used mainly as an email application, it also includes a calendar, task manager, contact manager, note-taker, journal, and web browser.

Outlook

Windows Server 2008 and Windows Server 2008 R2, based on the Microsoft Vista codebase, is the last 32-bit server operating system released by Microsoft. It has a number of versions, including including Foundation, Standard, Enterprise, Datacenter, Web, HPC Server, Itanium and Storage; new features included server core installation and Hyper-V.