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Im having trouble with having OpenSSL connect to a server because of trust issues. I placed the CA certificate on /etc/ssl/certs/ and have run sudo c_rehash and can see that the correct file has been made. I can see that CA certificate is in the ca-certificates.crt. However if I run:
openssl s_client -connect servername.domain.com:636
The command fails with Verify return code: 21 (unable to verify the first certificate)
If I do:
openssl s_client -connect servername.domain.com:636 -CApath /etc/ssl/certs/
I get Verify return code: 0 (ok)
What can I do so I dont have to specify the CApath?
I'm using Ubuntu 13.04.
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capath is used to define a directory that contains PEM encoded CA certificates that are trusted. For capath to work correctly, the certificates files must have ". pem" as the file ending and you must run "openssl rehash <path to capath>" each time you add/remove a certificate.
To verify that a certificate is installedOpen the Cerificates console. In the navigation pane, expand Trusted Root Certification Authorities, and then click Certificates. The CA that you created appears in the list.
By default, the Python ssl module uses the system CA certificate bundle - /etc/pki/tls/certs/ca-bundle.
To verify a certificate with it's CRL, download the certificate and get its CRL Distribution Point. In the output you should see the CRL url. Next, download the CRL with the wget function. It will be in der format, so we will be converting it to pem format for the openssl verify function to work.
You can also set and export the environment variables SSL_CERT_FILE or SSL_CERT_DIR...
export SSL_CERT_FILE=/path/to/ca_bundle.crt
export SSL_CERT_DIR=/path/to/ca/dir
Then you do not have to specify CAfile or CApath in every openssl command.
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OpenSSL connect to a server because of trust issues.
Unlike browsers, which trust nearly everything from anybody, OpenSSL trusts nothing by default.
Its up to you to determine what should be trusted. You will have to specify something when using OpenSSL and s_client.
If you are working programmatically with the OpenSSL API, you have more options. But this appears to be related to using the OpenSSL commands.
What can I do so I don't have to specify the
CApath?
You can use the CAfile. It avoids the rehash, and it creates a 1:1 mapping for trust of the domain. That is, you only trust one issuer for the domain in question. If any other issuer claims to be the issuer, you won't trust the issuer or the server.
You can see how to extract the needed info from OpenSSL's s_client and use CAfile at How to Grab SSL Certificate in OpenSSL.
When using all the certificates present in CAPath, you trust any issuer, even if its not the real issuer. This has happened in the past and its bad.
The corner case is where a bad guy compromises the CA you trust and issues phony certifcates for the domain. This has happened in the past too, and its bad.
In the two negative cases above, you can forgo conferring trust to DNS and CAs and use a security diversification technique like certificate or public key pinning. If there's a pre-existing relationship between you and the site, then you know the expected public key of the server. In this case, there's no need to trust a CA.
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