Jason,
Was the Cygwin binary version of PostgreSQL compiled with SSL support? 
Or does that require an actual compile from source?  Just curious.  Have 
never tried using SSL to connect, but I could see it's usefulness at 
some point in the future, so thought I'd go straight to the source.
I know OpenSSL is also offered as a Cygwin package, and I've compiled 
various items using it under Cygwin.  But was just curious whether 
PostgreSQL was already compiled against it.  I suspect not, since the 
OpenSSL package isn't listed in the README.