Secure Transport is deprecated.

[kitanic]

native-tls on Apple platform uses Secure Transport via security-framework crate, however it is already deprecated and unsupported.

Apple is asking for a move to the Network framework instead. I don't know if it is in this crate or in a sub-crate, implementation must be migrated.

[mmastrac]

Agreed. I've been seeing numerous crash and bug reports coming from Secure Transport -- it randomly throws permission errors for no discernable reason (possibly JAMF), and a user with nix installed is seeing Secure Transport in a crash report.

[sfackler]

How would that be implemented in a way that conforms to the native-tls APIs? In particular, the implementation needs to support a arbitrary stream under the TLS implementation.

[mmastrac]

To help Googleability of this issue -- this is a crash report that results from the interaction of Secure Transport + nix macOS.

(lldb) cont
Process 68893 resuming
Process 68893 stopped
* thread #9, name = 'edgedb-http', stop reason = signal SIGABRT
    frame #0: 0x000000019de715d0 libsystem_kernel.dylib`__pthread_kill + 8
libsystem_kernel.dylib`__pthread_kill:
->  0x19de715d0 <+8>:  b.lo   0x19de715f0    ; <+40>
    0x19de715d4 <+12>: pacibsp
    0x19de715d8 <+16>: stp    x29, x30, [sp, #-0x10]!
    0x19de715dc <+20>: mov    x29, sp
Target 0: (python3.12) stopped.
(lldb) bt
* thread #9, name = 'edgedb-http', stop reason = signal SIGABRT
  * frame #0: 0x000000019de715d0 libsystem_kernel.dylib`__pthread_kill + 8
    frame #1: 0x000000019dea9c20 libsystem_pthread.dylib`pthread_kill + 288
    frame #2: 0x000000019ddb6a30 libsystem_c.dylib`abort + 180
    frame #3: 0x000000010e606af0 libtcmalloc_minimal.4.dylib`tcmalloc::Log(tcmalloc::LogMode, char const*, int, tcmalloc::LogItem, tcmalloc::LogItem, tcmalloc::LogItem, tcmalloc::LogItem) + 760
    frame #4: 0x000000010e603868 libtcmalloc_minimal.4.dylib`(anonymous namespace)::InvalidFree(void*) + 64
    frame #5: 0x000000019e01e140 CoreFoundation`_CFArrayReplaceValues + 1112
    frame #6: 0x000000019df29384 CoreFoundation`CFArrayAppendValue + 152
    frame #7: 0x000000019e0323c4 CoreFoundation`_CFBundleAddToTablesLocked + 156
    frame #8: 0x000000019e01cd38 CoreFoundation`_CFBundleCreate + 1016
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    frame #10: 0x00000001a0c42680 Security`Security::MDSSession::DbFilesInfo::updateForBundle(char const*) + 652
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    frame #119: 0x000000010cfe2938 _http.cpython-312-darwin.so`std::sys_common::backtrace::__rust_begin_short_backtrace::h4cacfb6651d964dc + 16
    frame #120: 0x000000010cfe5258 _http.cpython-312-darwin.so`std::thread::Builder::spawn_unchecked_::_$u7b$$u7b$closure$u7d$$u7d$::_$u7b$$u7b$closure$u7d$$u7d$::ha0d0376f1bf3e976 + 44
    frame #121: 0x000000010cfcfc9c _http.cpython-312-darwin.so`_$LT$core..panic..unwind_safe..AssertUnwindSafe$LT$F$GT$$u20$as$u20$core..ops..function..FnOnce$LT$$LP$$RP$$GT$$GT$::call_once::hee995994c61cfd9a + 44
    frame #122: 0x000000010cfdef7c _http.cpython-312-darwin.so`std::panicking::try::do_call::h96a9a4e96d5ee24e + 76
    frame #123: 0x000000010cfdfe7c _http.cpython-312-darwin.so`__rust_try + 32
    frame #124: 0x000000010cfde7b4 _http.cpython-312-darwin.so`std::panicking::try::he345529e81bfd56d + 92
    frame #125: 0x000000010cfe50d0 _http.cpython-312-darwin.so`std::thread::Builder::spawn_unchecked_::_$u7b$$u7b$closure$u7d$$u7d$::hf94e01e7d9aebd5a + 404
    frame #126: 0x000000010d005468 _http.cpython-312-darwin.so`core::ops::function::FnOnce::call_once$u7b$$u7b$vtable.shim$u7d$$u7d$::hb6a41aaa76d2d7a5 + 24
    frame #127: 0x000000010d38ff1c _http.cpython-312-darwin.so`std::sys::pal::unix::thread::Thread::new::thread_start::hb184f2abd415aef7 [inlined] _$LT$alloc..boxed..Box$LT$F$C$A$GT$$u20$as$u20$core..ops..function..FnOnce$LT$Args$GT$$GT$::call_once::hf621d68debdec6cc at boxed.rs:2063:9 [opt]
    frame #128: 0x000000010d38ff10 _http.cpython-312-darwin.so`std::sys::pal::unix::thread::Thread::new::thread_start::hb184f2abd415aef7 [inlined] _$LT$alloc..boxed..Box$LT$F$C$A$GT$$u20$as$u20$core..ops..function..FnOnce$LT$Args$GT$$GT$::call_once::h4b545caf97b7e0d0 at boxed.rs:2063:9 [opt]
    frame #129: 0x000000010d38ff0c _http.cpython-312-darwin.so`std::sys::pal::unix::thread::Thread::new::thread_start::hb184f2abd415aef7 at thread.rs:108:17 [opt]
    frame #130: 0x000000019dea9f94 libsystem_pthread.dylib`_pthread_start + 136

[mmastrac]

@sfackler If possible, could we get native openssl (aka LibreSSL) support on MacOS instead?

[sfackler]

It's possible, but not really "native" then anymore.

[mmastrac]

I understand. It's stretching the limits of the word for sure, but a modern LibreSSL has been installed by default in /usr/lib for a while and it solves some of the deprecation issues.

[sfackler]

IIRC Apple does not want anyone linking to that and stopped shipping headers back when they switched from OpenSSL 0.9.8 to LibreSSL.

[mmastrac]

I tried to understand the state of LibreSSL support -- apparently Apple stopped shipping the OpenSSL headers but continued to update and maintain the LibreSSL binary itself.

TBH it's not clear what the state of this library is. It's possible that it's stable, but it's also possible that it exists purely to satisfy older MacOS apps and scripts that expect the openssl command-line tool.

drduh/macOS-Security-and-Privacy-Guide#356

OTOH, the Network.framework looks somewhat challenging to program against but not necessarily a bad fit.