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Re:Extracting TLS keys from an unwilling application (2020) by K0nserv on Tuesday May 24, 2022 @05:22PM (#31497680)
Not sure about the non-security expert bit but I've done stuff[0] similar to this for iOS using Frida[1] which supports macOS too. For apps that use unpinned certificates and the builtin networking libraries(NSURLSession et.al.) you can directly use mimtproxy[2] or Charles[3]

0: https://hugotunius.se/2020/08/07/stealing-tls-sessions-keys-...

1: https://frida.re/

2: https://mitmproxy.org/

3: https://www.charlesproxy.com/

Re:Extracting TLS keys from an unwilling application (2020) by youngtaff on Wednesday May 25, 2022 @04:02AM (#31501762)
I think you need to disable SIP to get a Frida based approach to work on MacOS

And while not MacOS this eBPF based approach is interesting https://mobile.twitter.com/quarkslab/status/1527726910997815...