> >     cert_extension_2 = X509.new_extension("keyUsage", "101000000") 
> 
> Maybe your OpenSSL is too old. keyUsage needs to be defined in OpenSSL
> obj_dat.h file for this to work.

I am using OpenSSL version 0.9.8k-fips which is the latest version. 

I replaced: 
cert_extension_2 = X509.new_extension("keyUsage", "101000000") 
with: 
cert_extension_2 = X509.new_extension("keyUsage", "keyCertSign,
cRLSign")

which worked for me. 

Also I found an easy way to iterate through the extension stack using:

cert = X509.X509()
for e in cert_extension_stack:
        cert.add_ext(e)

> >     cert_extension_3 = X509.new_extension("subjectAlternativeName",
> > "DNS:www.mydomain.tld")

> And I believe you mispelled this, try subjectAltName.

Changing "subjectAlternativeName" to "subjectAltName" did the trick. 

Thank you!

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