Rooting iOS

Jailbreak:

Installed OS X on VMware Workstation: https://www.sysnettechsolutions.com/en/install-macos-vmware/
    VirtualBox doesn't allow iphone to be connected to OS X, workarounds caused BSOD

Used OS X 12 - can find iso at: https://archive.org/details/macos-collection

Followed the Xcode + iOS App Signer instructions to load unc0ver jailbreak: https://unc0ver.dev/
    Xcode + iOS App Signer

    Install Xcode, open it, and agree to the license agreement.
    Plug in your iOS device and select it as the build target.
    Open Xcode and create a new iOS Application.
    Type a name and identifier.
    Xcode will complain about the lack of a provisioning profile. Click fix issue.
    Sign into an Apple ID when prompted.
    Download iOS App Signer
    Download the latest version of unc0ver from above.
    Open iOS App Signer.
    Select the ipa you just downloaded as an input file.
    Click start.
    Return to Xcode. Go to the menu bar. Click Window → Devices.
    Find your device, click the plus, and select the file created by iOS App Signer.
    Open unc0ver on your device and jail​break!

Adding Burp Proxy:

Added a new proxy via settings > wifi > i button > proxy

In burp edit interceptor to listen on all interfaces 

Visit http://burp on iOS and install the cert from settings > general

Install ssl kill switch 2 via cydia (see project README): https://github.com/nabla-c0d3/ssl-kill-switch2