Before, we were activating Let's Encrypt after all the directives were executed. This means their setup functions had access to potentially erroneous information about the server's TLS setup, since the letsencrypt package makes changes to the port, etc. Now, we execute all directives up to and including tls, then activate letsencrypt, then finish with the rest of the directives. It's a bit ugly, but I do think it is more correct. It also fixes some bugs, for example: a host that only has a catch-all redirect.
In testing, I've found that Windows doesn't release the socket right away even though the listener is closed, so calling caddy.Start() right after caddy.Stop() can fail. This change has server.ListenAndServe() try up to 20 times every 100ms to bind the listener, and only return an error if it doesn't succeed after 2 seconds. This might be kind of nifty for Unix, too, but there hasn't been a need for it yet.
The file path of the originally-loaded Caddyfile must be piped to the forked process; previously it was using stdin after the first fork, which wouldn't load the newest Caddyfile from disk, which is the point of SIGUSR1.
OCSP status is checked at a regular interval, and if the OCSP status changes for any of the certificates, the change callback is executed (restarts the server, updating the OCSP staple).
Merged config and app packages into one called caddy. Abstracted away caddy startup functionality making it easier to embed Caddy in any Go application and use it as a library. Graceful restart (should) now ensure child starts properly. Now piping a gob bundle to child process so that the child can match up inherited listeners to server address. Much cleanup still to do.
Lots of refinement still needed and runs only on POSIX systems. Windows will not get true graceful restarts (for now), but we will opt for very, very quick forceful restarts. Also, server configs are no longer put into a map; it is critical that they stay ordered so that they can be matched with their sockets in the child process after forking.
This implementation of graceful restarts is probably not perfect, but it is a good start. Lots of details to attend to now.