So I dug around and basically stared at the hard coded path of the certs. By typing this at the command line
ruby -ropenssl -e 'puts OpenSSL::X509::DEFAULT_CERT_FILE'
I got the following...
c:/Users/Luis/Code/openknapsack/knap-build/var/knapsack/software/x86-windows/openssl/1.0.0k/ssl/cert.pem
So my solution was to first download cacert.pem from http://curl.haxx.se/ca/cacert.pem to c:\ . Then open up Windows Control Panel -> Administrative Tools -> Windows PowerShell Modules. Then I proceeded to type out:
cd \
cd users
mkdir Luis
cd Luis
mkdir Code
cd Code
mkdir openknapsack
cd openknapsack
mkdir knap-build
cd knap-build
mkdir var
cd var
mkdir knapsack
cd knapsack
mkdir software
cd software
mkdir x86-windows
cd x86-windows
mkir openssl
cd openssl
mkdir 1.0.0k
cd 1.0.0k
mkdir ssl
cd ssl
cp c:\cacert.pem .\cert.pem
And now everything works! Yes it's a cheap hack and it's ugly. But now both you and I can get back to doing serious coding and not worry about pesky problems.
I know it's not a great fix, but it's the only thing that worked for me, and it should for you too.
If some one would like to write a PowerShell script to auto install the cert file into this directory then you could more easily deploy your Ruby project to Windows 7. Just a thought.
By the way, you can duplicate this process for any operating system should the need arise. Just find the path the cert file belongs in with:
ruby -ropenssl -e 'puts OpenSSL::X509::DEFAULT_CERT_FILE'
And be sure to rename the file as it appears in the ouput!