I'm on version 2.7.1 ... How would I go about launching my pex binary with debugpy debugging?

I've never used debugpy, but probably the easiest will be their import approach: https://github.com/microsoft/debugpy#debugpy-import-usage You'd add

debugpy

as a third-party dependency like you normally would. Then either

./pants run path/to:pex_binary

or

./pants package

it and then run from` dist/` folder