OS is 10.7.5 with all updates. Office 2011 with all updates up to 14.2.4

My work email is configured on Windows Outlook using cached Exchange mode (which I gather is the default for Mac Outlook, and cannot be disabled) I also have to set, under the "Connection" tab, "Connect to Microsoft Exchange uisng HTTP" and "Use this URL to connect to my proxy server for Exchange". I cannot find the equivalent of that in Mac Outlook. Further, I get zero feedback from Mac Outlook... no errors, no indication that it's even trying to do anything. I got the Progress and Errors windows open, and no matter how I try to configure my account, I don't get any information at all.

What do I need to do to get some kind of response from Outlook to start to figure out how to get my mail working?