I can think of _some_ suggestions, but it's been about 2 years since I've logged in to a Windows server and played with IIS... have you checked the Windows event log(s)?

Also, you might check to see if all dependencies for php_openssl.dll are satisfied (depends.exe), but that may actually be a non-issue. Like I said, it's been so long, and I don't have access to a Windows server these days.