The mistake I made was simple, I accidentally included the 64-bit dll: cygcrypto-1.0.0.dll Instead of the 32-bit version.

This mistake is fairly easy mistake because the package filename is the same for both 32-bit and 64-bit cygwin: libopenssl100-1.0.1i-1.tar.xz I'll release +build3 shortly with the correct .dll.