Utilising the existing IT infrastructure, the objective of this research is to develop an integrated Web-based distributed process planning system (Web-DPP) for job-shop machining operations and their runtime execution monitoring. Our approach tries to engage a dispersed working group in a collaborative environment, allowing the team members to share real-time information through the Web-DPP. This paper analyses the challenges, and presents both the system design specification and the latest development of the Web-DPP system. Particularly, it proposes a two-tier architecture for effective decision making and introduces a set of event-driven function blocks for bridging the gap between high-level planning and low-level execution functions. By connecting to a Wise-ShopFloor framework, it enables real-time execution monitoring during the machining operations, locally or remotely. The closed-loop information flow makes adaptive planning possible.