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From: "Pinzone, Gerard" <GPinzone@aaccorp.com>
To: "cygwin@cygwin.com" <cygwin@cygwin.com>
Subject: Re: OpenSSH FIPS 140-2
Date: Tue, 25 Jun 2019 13:45:06 +0000
Message-ID: <ef3aa80d58bf4c49b270264b494c77c2@aaccorp.com>
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I was able to build OpenSSL with FIPS and OpenSSH using those OpenSSL libraries from scratch and install on 32-bit Cygwin.

I'm documenting what I did here and would like some feedback. 

Install Cygwin 32-bit with the following extras:
-----------------------------------------------

Rollback OpenSSL to latest 1.0.2
zlib (all)
Perl (all)
zip
unzip
gcc-g++
make

Extract all files:
-----------------

tar -zxvf openssl-fips-2.0.16.tar.gz
tar -zxvf openssl-1.0.2s.tar.gz
tar -zxvf openssh-8.0p1.tar.gz

Build OpenSSL:
-------------

cd openssl-fips-2.0.16

./config
make
make install

cd ../openssl-1.0.2s

./config fips --with-fipsdir=/usr/local/ssl/fips-2.0
make depend
make
make install

cd apps

Verify build:
------------

./openssl version -a

Install OpenSSL:
---------------

mv /usr/bin/openssl.exe /usr/bin/openssl.exe.old
cp openssl.exe /usr/bin/openssl.exe

Build OpenSSH:
-------------

cd ~/openssh-8.0p1

./configure --with-ssl-dir=/usr/local/ssl --with-ssl-engine
make
make install

Install OpenSSH:
---------------

cp scp.exe /usr/bin/.
cp sftp.exe /usr/bin/.
cp sftp-server.exe /usr/sbin/.
cp ssh.exe /usr/bin/.
cp ssh-add.exe /usr/bin/.
cp ssh-agent.exe /usr/bin/.
cp sshd.exe /usr/sbin/.
cp ssh-keygen.exe /usr/bin/.
cp ssh-keyscan.exe /usr/bin/.
cp ssh-keysign.exe /usr/sbin/.
cp ssh-pkcs11-helper.exe /usr/sbin/.


Verify ssh:
----------

ssh -vvv localhost

Configure sshd:
--------------

ssh-host-config -y
cygrunsrv -S cygsshd

Generate keys:
-------------

ssh-keygen

Test sshd:
---------

ssh localhost

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