We introduce an improved one-shot characterisation of randomness extraction against quantum side information (privacy amplification), strengthening known one-shot bounds and providing a unified derivation of the tightest known asymptotic constraints. Our main tool is a new class of smooth conditional entropies defined by lifting classical smooth divergences through measurements. A key role is played by the measured smooth Rényi relative entropy of order 2, which we show to admit an equivalent variational form: it can be understood as allowing for smoothing over not only states, but also non-positive Hermitian operators. Building on this, we establish a tightened leftover hash lemma, significantly improving over all known smooth min-entropy bounds on extractable randomness and recovering the sharpest classical achievability results. We extend these methods to decoupling, the coherent analogue of privacy amplification, obtaining a corresponding improved one-shot bound. Relaxing our smooth entropy bounds leads to one-shot achievability results in terms of measured Rényi divergences, tightening the bounds of [Dupuis, arXiv:2105.05342] and recovering state-of-the-art asymptotic i.i.d. error exponents. We show an approximate optimality of our results by giving a matching one-shot converse bound up to additive logarithmic terms. This yields an optimal second-order asymptotic expansion of privacy amplification under trace distance, establishing a significantly tighter one-shot achievability result than previously shown in [Shen et al., arXiv:2202.11590] and proving its optimality for all hash functions.

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