buck wrote:
> I have googled and not found anything appropriate. If anyone can supply
> some keywords for my search, please do.
>
> stunnel connects to news.newsguy.com on port 563. How can I know that this
> transmission is encrypted?

Two options come to mind.

1. Do a packet capture with tcpdump, wireshark, etc., and watch the SSL
encryption type get negotiated. That part's always in the clear.

2. Although I haven't ever done it myself, crank up the debug level.
stunnel comes with its own documentation. I could be better, but check
out the debug and output parameters in stunnel.conf.