We have developed a theory of air leakage at interfaces between two elastic solids with application to suction cups in contact with randomly rough surfaces. We present an equation for the airflow in narrow constrictions which interpolate between the diffusive and ballistic (Knudsen) air-flow limits.To test the theory we performed experiments using two different suction cups, made from soft polyvinylchloride (PVC), in contact with sandblasted polymethylmethacrylate (PMMA) plates. We found that the measured time to detatch (lifetime) of suction cups were in good agreement with theory, except for surfaces with the root-mean-square (rms) roughness below ≈ 1 µm, where diffusion of plasticizer from the PVC to the PMMA surface caused blockage of critical constrictions. Suction cup volume, stiffness and elastic modulus have a huge influence on the air leakage and hence the failure time of the cups. Based on our research we propose an improved biomimetic design of suction cups, that could show improved failure times in varying degree of roughness under dry and wet environments.