Use Bash with run_in_background=true to run: for i in $(seq 1 6); do sleep 5; echo "{\"i\": $i}" >> ./results-c.jsonl; done Then arm a Monitor (timeout_ms 60000) that prints one line for every new line in ./results-c.jsonl, and end your turn. Each time you're notified, reply with one short sentence and end your turn again. Do not call t3_background_wait.