Jarzynski’s equality sets a strong bound on the probability of violating the second law of thermodynamics by extracting work beyond the free energy difference. We derive finite-time refinements to this bound for driven systems in contact with a thermal Markovian environment, which can be expressed in terms of the geometric notion of thermodynamic length. We show that finite-time protocols converge to Jarzynski’s bound at a rate slower than 1/√τ , where τ is the total time of the work-extraction protocol. Our result highlights a new application of minimal dissipation processes and demonstrates a connection between thermodynamic geometry and the higher order statistical properties of work.