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tcpdump -nnAs0 -i eth0 port 514

As I understand it this should display any logging msgs sent to syslog locally. However I send many via python syslog module, which I can tail via /var/log/messages but do not show up when listening to port 514.

I want to send to this port, how do I do so?

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If the messages are appearing in the logs, they are being sent and received by syslog.

The problem with your command is that the machine to communicate with itself does use the loopback interface.

So, you are listening to the wrong address in your tcpdump.

To see the packets of the communication with syslog do:

sudo tcpdump -nnAs0 -i lo port 514

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