@ghadi are you talking about instrumenting cider midddleware in particular? Or just midddleware in general?

Cider midddleware is tricky, since the debugger itself is a midddleware, instrumenting other parts of cider might not work.

General midddleware should work just fine. I used to work with ring and pedestal, and had no problems instrumenting either of them.

newbie question: what's the best way to load a new dependency when using CIDER + nREPL?

so far I've been restarting CIDER + nREPL

you mean a new dependency in your project.clj or boot file?

exactly

if so, you're gonna want clojure-refactor https://github.com/clojure-emacs/clj-refactor.el/wiki

https://github.com/clojure-emacs/clj-refactor.el/wiki/cljr-add-project-dependency