Networks-on-chip (NoC) are a scalable interconnect solution for systems on chip and are rapidly becoming reality. Monitoring is a key enabler for debugging or performance analysis and quality-of-service techniques. The NoC design problem and the NoC monitoring problem cannot be treated in isolation. We propose a monitoring-aware NoC design flow able to take into account the monitoring requirements in general. We illustrate our flow with a debug driven monitoring case study of transaction monitoring. By treating the NoC design and monitoring problems in synergy, the area cost of monitoring can be limited to 3-20% in general.