MonkeyDev VS ssl-kill-switch2

I can't read a lot of that project, but what I can doesn't look like you'll be able to do that on an iPhone. If you look at the installation section, it's expecting you to be building this on a mac: https://github.com/AloneMonkey/MonkeyDev/wiki/Installation (that isn't called out explicitly, but it's implicit in the commands they're running). "Easy to install" in this case seems to be for someone who is familiar with writing custom iOS applications and has a development setup for that already.

Theos is the easiest way to do it imo but you can still use Xcode with something like MonkeyDev if you want to. Either way you'll need to install theos

Another tip is looking at the source code of well-known tools that feature root/jailbreak/cert pinning bypasses like Objection, SSL Kill Switch 2, and Shadow to learn reverse engineering stuff.

Sadly, the tweak (source: https://github.com/nabla-c0d3/ssl-kill-switch2) doesn't work on iOS 14 after installing (and calling Frida every time to disable Certificate Pinning is too annoying). Will gladly pay $50 to anyone that makes it work on A8 devices (I'm using iPad Mini 4) on iOS 14 (I'm using iOS 14.4.2). Thanks.

Jailbreaking an iPhone and using a tool like SSL Kill Switch [1] or just plain, old Frida with a script like [2] will do the job. Jailbreaking is the hard part, especially for an up to date iPhone, after that there's loads of guides you can follow that disable certificate validation for pretty much every application. It all boils down to hooking the necessary validation functions and having the APIs lie to the app code.

Some apps package their own crypto helpers (often with big crypto problems) to make this harder and require actual reverse engineering, but those are a pain to maintain and it's only a matter of time before someone finds a way around them. If you can extract the symbols (so if the app has not been obfuscated well) you can use Frida's API to hook those as well through any language you like. There's even an interactive Javascript console you can hook into the apps you're hooking!

Certificate pinning is a great way to protect users' security and privacy, especially in countries with questionable governments or ISPs, but it won't protect your app's secrets.

[1]: https://github.com/nabla-c0d3/ssl-kill-switch2