OpenSSL 0.9.8zc -> 0.9.8zd "broke" my certificates.

Question

I have a self-signed certificate (and CA) created on a Mac using OpenSSL 0.9.8zc. I use the certificate to secure connection to my svn server. With the latest OS X update, OpenSSL was updated to 0.9.8zd. Now I cannot connect to my server, I get "certificate verify failed" from svn.

Using openssl verify:

openssl verify -CAfile ~/Desktop/Certificates.pem -check_ss_sig  ~/Downloads/svn.pem

I get

~/Downloads/svn.pem: /CN=My Open Directory Certification Authority/O=Me/OU=MACOSX OpenDirectory Root CA/emailAddress=webmaster@me
error 7 at 2 depth lookup:certificate signature failure

It looks like the signature of my CA is now considered "broken". My questions:

1. How can I investigate further to figure out what is "broken" exactly about my certificate, so I do not repeat this mistake?

2. Is there a way to fix this short of reissuing every certificate starting with CA?

Answer 1

It seems this is a problem with Certificate Assistant producing subtly malformed certificates that the new tighter checks of openssl 0.9.8zd reject. This comes from a discussion at openssl.org 1

It includes at the end a python script to fix a .pem certificate which I managed to use successfully, I quote it in case the link is broken...

from pyasn1.codec.der import decoder, encoder   
from pyasn1_modules import pem, rfc2459

cert_der = pem.readPemFromFile(open("RabbitMQ_Test.pem", "r"))
        cert, _ = decoder.decode(cert_der, asn1Spec=rfc2459.Certificate())

cert.setComponentByName("signatureAlgorithm",
                                cert.getComponentByName("tbsCertificate").
                                getComponentByName("signature"))

fixed_cert_pem = open("RabbitMQ_Test_Fixed.pem", "w")
fixed_cert_pem.write("-----BEGIN CERTIFICATE-----\n")
fixed_cert_pem.write(encoder.encode(cert).encode("base64"))
fixed_cert_pem.write("-----END CERTIFICATE-----\n")
fixed_cert_pem.close()

Answer 2

If you're on OS X 10.10.3 and this just started happening:

NB: This is a temporary workaround, it seems like the problem is further upstream

I suddenly started having this error appear as a result of upgrading OSX to 10.10.3 - as you said, it seems that the break is caused by the new version of OpenSSL (0.9.8zd) they have included.

As a workaround until we get to the bottom if this, I made use of homebrew's OpenSSL package -

$ brew update
$ brew install openssl
$ brew link openssl --force 

you might also need to update stale certs, which with rvm is just a case of running

$ rvm osx-ssl-certs update all

But by the sound of it you know what you're doing there

It's also worth noting that homebrew recommends against linking openssl, so once this is sorted out upstream you will probably want to run this to clean up the mess we made:

$ brew unlink openssl 

Answer 3

I had a similar problem when trying to connect to an Apache server running on 10.10.3 using client & server certificates. The python script worked on the SSL server certificate for Apache to use, but Safari still couldn't connect to the server using the client certificate in the keychain; the Apache server was rejecting the client certificate.

I had to export the client certificate, use the python script on it, and import it back into the keychain to replace the original.