Tim Pushor wrote:
May be a dumb question, but how do I look at traffic going over an IPSEC tunnel, on one of the OpenBSD machines? I've tried tcpdump -i enc0 but get nothing ..

That is exactly what you do.  Remember you can not use filters on it, no

tcpdump -i enc0 host wakkawakka

if plain old  tcpdump -i enc0
is not showing anything then probably you are not actually encrypting.

Does
tcpdump -i outside_iface

show you ESP traffic
does
netstat -rnf encap

show tunnels?

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