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The bounds presented at CHES 2017 based on Massey’s guessing entropy represent the most scalable side-channel security evaluation method to date. In this paper, we present an improvement of this method, by determining the asymptotically optimal Massey-like inequality and then further refining it for finite support distributions. The impact of these results is highlighted for side-channel attack evaluations, demonstrating the improvements over the CHES 2017 bounds.