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How would you create a SSL self-signed certificate via the CLI (Command Line Interface) for an OpenSIPS Server and a Media Proxy Server?

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Try this, see section 1.5.1 http://www.opensips.org/html/docs/tutorials/tls-1.4.x.html#AEN125

You may need to import the root CA certificate into the client machines manually, depending on the OS.

You can also try this link for OpenSSL

http://www.akadia.com/services/ssh_test_certificate.html