Analyze a TLS handshake

Short blogpost on a quick way to analyze a TLS handshake:

In one terminal, setup the server:

openssl req -x509 -newkey rsa:2048 -keyout key.pem -out cert.pem -nodes
openssl s_server -cert cert.pem -key key.pem

The first command use the req toolkit of openssl. It is usually used to create certificate request (and the request is then later approved by a CA), but since we’re in a rush, let’s just use it with the -x509 option to directly generate a certificate. rsa:2048 generates a key with the algorithm RSA and with a modulus of size 2048 bits. -nodes disable the use of a passphrase to protect the key (the default protect the key by encrypting it with DES).

In a second terminal, start capturing packets:

tcpdump -i lo0 -s 65535 -w exchange.cap

65535 is the maximum length of a packet.

Start a handshake in a third terminal:

openssl s_client -connect localhost:4433

Now open the .cap with Wireshark!