objection VS ssl-kill-switch2

This is true, by default Android apps do not trust user-installed certificate authorities. IMO the easiest solution if you're doing security testing on a dedicated device is MagiskTrustUserCerts[1]. If you're not testing on a dedicated device or you don't want to root the device, I'd recommend using the objection[2] tool which has a guided mode for patching an apk, and you can modify the manifest to add your CA or to trust all user-installed CAs.

[1]: https://github.com/NVISOsecurity/MagiskTrustUserCerts

[2]: https://github.com/sensepost/objection/wiki/Patching-Android...

Then use runtime tools like Runtime Mobile Security, Grapefruit, and Objection to see stuff in action and practice Frida along with as these tools usually support loading custom Frida scripts.

you might have more luck in some whitehat hacking groups etc. ive used https://github.com/sensepost/objection to try out my own app.

In some form yes. Internally this is just a Frida gadget script which you can see here does support IOS.

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