I've been able to build OpenSSL 1.0.2 with FIPS support on Cygwin 32-bit and 
native Windows using Visual Studio. The 64-bit edition of Cygwin doesn't build 
the FIPS module correctly. There is a workaround, but that workaround 
invalidates the FIPS build requirements, thus the resulting binary will not be 
approved without a private certification that costs lots of $$$. I'd like to 
get OpenSSH to work with the OpenSSL I've built under 32-bit Cygwin, but that 
might require a custom build of OpenSSH. The latest Cygwin uses the newer 1.1.1 
branch of OpenSSL, so I don't know if that will cause any compatibility 
problems.

Having a FIPS 140-2 OpenSSH on a Windows OS is important for those in the 
financial and government sector. Microsoft's port of OpenSSH uses LibreSSL (I 
think) and cannot be FIPS certified. It looks like Cygwin is our only hope.

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