A disclosed method may include (1) collecting telemetry data that represents a state of a network device during a live operating session, (2) deriving, from the telemetry data, a set of steps for reproducing the state of the network device during the live operating session based at least in part on a set of rules, (3) generating, based at least in part on the set of steps, a playback decision tree that, upon execution, facilitates (A) reproducing the state of the network device during the live operating session and (B) debugging the state of the network device, and then (4) performing a debug operation that executes the playback decision tree via a network diagnostic tool such as a healthbot. Various other systems, methods, and computer-readable media are also disclosed.