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Ok, so after nearly three (3) hours on the phone with Microsoft, I was able to get the issue fixed. This is what I did...
Open "regedit"
Navigate to "HKEY_CURRENT_USER\SOFTWARE\Microsoft\Office\16.0\Outlook\AutoDiscover"
On the right, right-click, select "New" -> "DWORD (32-bit) Value"
Name it "ExcludeHttpsRootDomain"
Double-click the value after adding and set "Value data" to "1" and leave Base as Hexadecimal
What was causing the issue...
Evidently the root domain server was actually responding to the "autodiscover" request so outlook never made it to "AutoDiscover.[Domain.com]", it held up at "[Domain.com]:443". By adding this registry entry, it is telling outlook to ignore the root domain and go directly to the next option on the list (e.g. "Autodiscover.[Domain.com]".
Hopefully this will help someone else having a similar issue.