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Has anyone found a good way to on-premise test SSL/TLS certs for many (100's) of sites on a regular basis?

The usecase is websites setup both internally, and with VPN tunnels to many customers, as such no internet-facing presence.

Things to check:

  • does the cert match the dns/url name
  • are all the intermediate certs accounted for
  • is it expired
  • is it signed by a trusted thirdparty site (commonly recognized by browsers)

bonus for:

  • are there weak ciphers allowed
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I don't know of any tools that do this pre-made. But a loop and a list of your cert files in a shell with openssl installed should do it. To verify the full chain, check out the openssl verify command. Something like this should work:

openssl verify -CAfile root_cert.pem -untrusted intermediate_cert.pem user_cert.pem

You can also add multiple intermediate certs as well. For each one just add another -untrusted flag for the cert.

There are a few specific pre-made tools that will verify supported ciphers. Check out sslscan to test ciphers.

Again, with a few loops in your preferred shell (bash for example), you can achieve a similar effect. Just make sure you have the openssl client installed and run something like:

openssl s_client -showcerts -cipher <test_cipher> -connect <your_endpoint>:<tls_port>

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