This paper demonstrates the use of a flexible instrumented stamp to enable automated micro transfer printing as a route to large-area, deterministic assembly of microstructured device components or 'inks'. The ability to instrument the stamp, a critical component for retrieval and placement of a micro device, to detect contact and monitor localized forces during critical events in the printing process not only allows for the development of a robust manufacturing process, but also for a unique vantage point from which to study fundamental issues and phenomena associated with adhesion and delamination of thin films from a variety of substrate materials. This paper presents basic design analysis on the requirements of the cantilevers for compatibility with a typical transfer printing environment. Off-the-shelf thin film strain gages are integrated with a thin elastomeric post as a preliminary prototype and the feasibility of transfer printing with it is demonstrated. Further, the set-up is calibrated to produce force signals for event detection and in-situ diagnosis of the process.