I think the proper technique was using conditional jumps (that always end up jumping) so the disasm thinks the next instruction should come right after it (in case the jump isn't taken). It then becomes undecidable which is the correct path.

_edit_

Huh, you're right, IDA works around some basic examples I threw at it. Who knew.

_edit_

Oh, I forgot to strip symbols... successfully managed to confuse IDA with a few tries :)

https://gist.github.com/tostercx/899630ba3d01cb98fcf7faf8bf0...