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Developers link against system OpenSSL, so Apple can basically never upgrade it.

I'm not sure that Apple promised to stay with OpenSSL. Apple developed CryptoCommons wrapper for some OpenSSL methods and I'm sure, that they can make it work with LibreSSL. I was under impression that it was made specifically to be able to drop OpenSSL when they would want it.

Those are the newer libraries you're _suppose_ to use, rather than OpenSSL. It's mostly older applications and codebases that limit Apple. I could imagine a stop-point but Apple obsesses a lot about not breaking backwards compatibility.

Don't forget their version is ancient (API-wise; they back-port fixes) and LibreSSL is much newer, so it's not a drop in replacement for such an old version.

> obsesses a lot about not breaking backwards compatibility

Lo, how times have changed. ;-)

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