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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.

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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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