Foolishly, I trusted it to create /usr/local/var/lib/stunnel/ with the correct permissions. The directory that appeared had these permissions: ls -ld /usr/local/var/lib/stunnel/ drwxrwx--T 2 root wheel 68 Jan 5 16:55 /usr/local/var/lib/stunnel/ When I replaced it with this directory ls -ld /usr/local/var/lib/stunnel/ drwxrwxrwx 3 root wheel 102 Jan 5 20:43 /usr/local/var/lib/stunnel/ Suddenly, when I ran stunnel, it continued to run. I'd call this a bug. Still not doing quite what I want, (not connecting to elsewhere.com like I expect) but I'm closer. David Chase