This research presents a comprehensive approach to anticipate failures in ageing masonry arch bridges. By combining laboratory experiments and analytical models, a robust framework is proposed to anticipate damage progression and prevent catastrophic collapses. The methodology is validated through laboratory testing on a scaled multi-span and multi-ring masonry arch bridge. The experimental campaign aims at introducing typical damage patterns to study their evaluation, as well as to validate the proposed tools and techniques for monitoring damage evolution and predict failure. The design and validation of the experiments are supported by a set of analytical approaches considering different levels of accuracy and complexity, i.e., limit analysis, FEM macro-modelling and micro-modelling. Each method addresses different challenges, such as capturing the complex behaviour of masonry materials and the interaction between structural elements. The combination of different modelling techniques provides a robust foundation for predicting damage formation and collapse mechanisms in the investigated specimen. The results of the research, conducted as part of the Pont3 coordinated project in Spain, contribute to the development of a validated framework for preventing the collapse of ageing masonry arch bridges. By integrating state-of-the-art monitoring tools and analytical methods, the project seeks to enhance the safety and resilience this critical infrastructure.