This repository contains tools and scripts that will create a somewhat optimal debug environment.
as of writing, checkra1n beta 0.9.5 is not working with this specific iPad. A workround is to use 0.9.2
in order to run debugserver on iOS 13 and being able to attach or launch any process, you need to follow those steps:
on your mac run security find-identity -v -p codesigning and copy whatever is shown there "iPhone Developer: Mila432 (...)"
download the ent.xml file from scripts and run codesign --force --sign "iPhone Developer: Mila432 (...)" --entitlements ent.xml -f debugserver
now copy debugserver to your device /usr/bin/