As it happens, one way or another (and I'm not entirely sure
*which* way; I'd have to look at my notes), we *do* have Tomcat
listening directly on 443 (but not 80; nothing there is currently
listening on 80) on that particular EC2 instance (and I'm pretty
sure we have HTTPD running on a *different* port, for the SVN and
Trac sharing the box).

Hmm. It seems I was mistaken about two things: (1) that the Tomcat server under discussion is listening *directly* on 443, and (2) that I could find my notes on how I set the box up.

What I can find is the server.xml file, and the active connector definition. The thing that catches my eye is
port="8443" proxyPort="443"

I hope that indicates how it is I'm getting this to look like port 443 to the outside world, because I honestly can't remember what I did (even though it looks like it's only been six months since I did it).

I now know one thing that I apparently did *not* do: I did *not* have HTTPD handle the public-facing TLS for Tomcat, because when I swapped in a self-signed keystore on Tomcat, and used the new "Re-read TLS configuration files" button in Manager, the self-signed cert is what was visible to browsers.

Trac and SVN do indeed appear to be set up through HTTPD. And the Tomcat and Apache files appear to share a common keypair and certificate, and I'm pretty sure I remember *starting with* a Java Keystore (since it's very familiar territory for me, and since I have KeyStore Explorer on my Mac), and exporting files from it, i.e., (the names have been changed to protect the innocent), I started with "/etc/tomcat8/foo.bar.net.ks," and derived "/etc/pki/tls/certs/foo.bar.net.cer," "/etc/pki/tls/certs/foo.bar.net.ca.crt," and "/etc/pki/tls/private/foo.bar.net.key" from it.

Am I to understand that Tomcat 8.5.40 can use the ".cer," ".ca.crt" and ".key" files directly, instead of the Java Keystore file? If so, then that could potentially simplify things: if I have HTTPD listen on 80, and Tomcat sharing the same actual certificate and private key *files* that HTTPD uses, then the only other thing I have to automate would be a cron job to either restart Tomcat, or just do a programmatic "re-read TLS configuration," whenever the regular Let's Encrypt job for HTTPD completes.

Does any of this make any sense at all, or am I sucking antimatter?

--
James H. H. Lampert

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