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Moving discussion over from: JuliaLang/MbedTLS.jl#125 (comment)

Re: ... a package that integrates with an OS's native TLS toolkit ...

I don't know if I'll have time to work on this any time soon, but I though it was worth making some notes given that it's been on my mind. I've sketched out some ideas here:
https://github.com/samoconnor/TLSClient.jl/blob/master/README.md

JuliaLang/MbedTLS.jl#125 (comment) :

I'll just say that for historical context, there have been somewhere between 2-5 distinct attempts at writing OpenSSL bindings for Julia in the past. I'm not going to try to comprehensively list them, but you can look around and find them - to my knowledge none have seen any development at any time within the last year or two, or longer. There was GnuTLS.jl which was actively used for a while (mostly for license compatibility reasons) but it had its set of problems and fell out of favor rapidly as soon as Jon wrote this package and got it up and functional.

When you work with OpenSSL, you also need to worry about how its API has changed over time, and the widely varying versions out there in the wild on different ages of Linux distro. The forks like LibreSSL and BoringSSL are also viable options. I don't know whether anyone has tried to write Julia bindings for WinHTTP or SecureTransport.

https://blog.regehr.org/archives/1261 is also an interesting anecdote, but from a few years ago.