The new Common Agricultural Policy (CAP) proposal includes few improvements compared to previous programming periods which may reinforce future evaluation, but we can also observe elements that may weaken the assessment, with the risk of repeating past failures. The objective of this essay is to analyse the new framework proposed for evaluation in the future CAP and to promote a collective discussion on how to make evaluations more usable, useful and reliable for users and practitioners. The first part of the paper analyses the main elements of evaluation during the different rural development programming cycles. A second part is dedicated to an examination of the current programming period (2014–2020) and the implications of the introduction of the Common Monitoring and Evaluation Framework (CMEF) and the evaluation plan. In a third part, we critically discuss the proposals for the next programming period and we offer some concluding reflections and two main open questions. From the analyses carried out, many elements emerge to encourage discussion on the role that evaluation has played and can play and the critical points to face. The experiences in rural development policies have introduced important changes in theoretical and implementation terms. In particular, they helped to build evaluation capacity and enabled the involvement of the civil society. However, it is also clear that the European Commission (EC) designed path has often led to an increase in rigidity and orthodoxy towards common frameworks compliance.