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When I access the site from the server itself (via remote PC) or within the network using the name of the machine I can access the site just fine, but when I try to use the external IP of the server I get generic errors If I specify the path completely (i.e. https :// server/MYApp/Default.aspx) I get:

"The resource cannot be found." in a standard ASP.Net error page style

If I specify just the virtual directory (i.e. https :// x.x.x.x/MYApp/) I get:

"The system cannot find the file specified."

I'm pretty sure that it is able to connect to the ip address since it's downloading the security certificate ok and it's coming back with an actual error page.

I'm not exactly sure which details will be most useful but I would appreciate any help if anyone has encountered a similar error before.

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It sounds to me like your site is not set to listen on the external ip of the server, go into the site bindings and add that in. By the sounds of it, your default site is listening on that ip so you may need to either add a host header with this, or remove the ip from the default site.

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