This week I upgraded one of my OpenSMTPD email servers to OpenBSD 5.6/OpenSMTPD 5.4.3 and all of a sudden I started having all kinds of TLS cert verification interoperability problems with my existing FreeBSD OpenSMTPD 5.4.2 server.

I was pulling my hair out trying to find out what heck was going on. After much flailing and gnashing of teeth I finally found the answer.

The CAcert root was pulled from OpenBSD 9 months ago, due to "strict requirements on redistribution". http://cvsweb.openbsd.org/cgi-bin/cvsweb/src/lib/libssl/Attic/cert.pem?rev=1.24&content-type=text/x-cvsweb-markup

This really sucks, because now I have setup my own Root CA for all my private facing TLS only email servers or fork over yet more $$ to the worthless commercial cert racket.

I know this wasn't anything directly caused by OpenSMTPD, but if anyone else is using CAcert.org certs and you're thinking about upgrading from OpenBSD 5.5 to 5.6, watch out for this.

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