On Wed, Jul 29, 2020 at 02:57:33PM -0700, Jeremy Evans wrote:
> After an OpenBSD upgrade, one of Ruby's tests for SSL session
> reuse started to fail.  After some debugging, I have found that
> if a maximum SSL version is not set by a client, then session
> reuse does not work.  Setting a minimum version does not have
> an effect.

This is an expected side-effect of switching TLS_method() to default to
TLSv1.3

https://github.com/openbsd/src/commit/94149d15d762bdbf7eef74c417c53d2b8dc7dd12

By setting the max version to TLSv1 with :TLS1 (or any of the other
defined versions :TLS1_1 or :TLS1_2), you use the legacy stack which
supports session resumption. The minimum version is already TLSv1, so
setting the minimum version to :TLSv1 has no effect.

In TLSv1.3, the session resumption feature has been merged with
pre-shared keys, which we may eventually support, but that's not going
to happen very soon:

https://tools.ietf.org/html/rfc8446#page-15

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