How can I get the session ID from the $CLIENT socket?

I think you would have to patch Net::SSLeay.

If I enable the session caching, do I renegotiate each time new connection arrives?

Yes, but its shorter negotiation. See SSL.

If the session id is different every time, how can I understand that the caching is working? Wireshark? or debug?

Not sure. A simple way would be to benchmark (with cache should be faster).

In reply to Re^3: IO::Socket::SSL Server-side Session caching by Anonymous Monk
in thread IO::Socket::SSL Server-side Session caching by dpetrov

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