The “happens after I setup a new .venv” detail is probably the most useful clue here, that pattern usually points to a version mismatch rather than a flow logic bug. CrewAI’s loop behavior shifted around the LiteLLM transition (issue #1355 in the repo touches on related agent-loop symptoms), and a fresh venv often pulls a newer LiteLLM than the last one that worked. For anyone landing here with the same symptom: first thing to check is pip freeze | grep -E 'crewai|litellm' against your last working environment.
Hiba out of curiosity, did the loop hit on a specific @listen Step or across all of them?