However, there is a faint chance that some Visual Studio utility or security update back-ported to Windows 7 will fix the problem. The Windows 7 problem was fixed by the release of Windows 8.1. This suggests to me that the problem is not with portman.sys: the problem is with the win32 compatibility layer in Windows 7/64 bit: It doesn't support debug properly. However, I don't see a copy of those files in SysWow64. Libraries, and they aren't actually missing: if they were, Windows wouldn't boot.
On my copy of Windows 7 64 bit, Microsoft Dependency Walker (depends.exe) tells me that PORTMSYS.SYS (the file created/loaded by Portmon.exe), has unresolved dependencies on ci.dll, clfs.sys, hal.dll and kdcom.dll.
Originally, you got this error when you tried to run Portmon from a network location: that broke the security trust, causing Portmon to be untrusted (or perhaps just messing up the search path somehow). "Error 2" is "Cannot find the file specified", that is, cannot find a required DLL file.
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