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This paper addresses the challenge of reliability-driven testing, i.e., of testing software systems with the specific objective of increasing its operational reliability. We first examined the most relevant approach oriented toward this goal, namely operational testing. The main issues that in the past hindered its wide-scale adoption and practical application are first discussed, followed by the analysis of its performance under different conditions and configurations. Then, a new approach conceived to overcome the limits of operational testing in delivering high reliability is proposed. The two testing strategies are evaluated probabilistically, and by simulation. Results report on the performance of operational testing when several involved parameters are taken into account, and on the effectiveness of the new proposed approach in achieving better reliability. At a higher level, the findings of the paper also suggest that a different view of the testing for reliability improvement concept may help to devise new testing approaches for high-reliability, demanding systems.