Differences between Apple Mail and Outlook using EWS

I know that this issue has been beat to death, so I'm requesting some very specific information to help with troubleshooting. My work has an uncooperative IT department that has indicated if I do the research myself, they will see if they can fix whatever settings are off in Exchange.
Details:
I'm using 10.9.3 and trying to connect to an Exchange 2010 server. When using Outlook 2011, everything works perfectly, when using ActiveSync on iPhones and iPads, everything works perfectly, but everything fails when using Apple Mail.
When using AutoDiscover with Apple Mail, it sets both internal and external servers to webmail.domain.edu, which ends up not working. After some looking around, I set the internal server to xxx-xxx-xxx-02.domain.edu and it starts working perfectly, as long as I'm accessing from within the network. Accessing outside the network results in errors.
Connecting to the Exchange server from my school works perfectly.
So my question boils to: What Exchange Server 2010 or EWS settings may make it possible for Outlook 2011 to easily access anywhere, but Apple Mail to fail when AutoDiscover is used anywhere and fail when manual server information is entered and attempted to access outside the network? Absolutely any leads would be appreciated.
I've run Microsoft Remote Connectivity Analyzer and it's worked perfectly.
Relevant log portions from failures (with certain information scrubbed)
When AutoDiscover is used:
<Autodiscover xmlns="http://schemas.microsoft.com/exchange/autodiscover/responseschema/2006>
    <Response>
        <Error Time="11:10:44.4955481" Id="1505556818">
            <ErrorCode>600</ErrorCode>
            <Message>Invalid Request</Message>
            <DebugData/>
        </Error>
    </Response>
</Autodiscover>
When internal server is manually entered and attempted to access outside the network (works inside the network)
2014-06-02 11:08:29.641 Mail[8898:9303] EXCHANGE -[SOAPRequest:0x7fe52f462c10 connection:didFailWithError:] https://domain%[email protected]/EWS/Exchange.asmx//domain%[email protected]/EWS/Exchange.asmx ERROR
NSURLErrorDomain -1003 A server with the specified hostname could not be found.
I'd love any brainstorming thoughts. Anything that could help me would be much appreciated. Thank you.

We are running Exchange 2013 here with auto discovery enabled. We have checked all the MS documentation and our auto discovery is stop correctly, auto discovery does work as the internal server is discovered however as the first post describes email isn't working with outside the internal network without a VPN connected. One of the guys is leaning towards it being a TLS issue but could just be a stab in the dark. I've got 3 people from our IT department as well as myself looking into the issue and if we find out what is actually going on, I'll post.

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