When an individual charged with a criminal offense is convicted and sentenced to imprisonment, the question arises as to whether the higher courts exercising judicial review should stay the sentence until the result of such a review is determined. The question is particularly interesting in the context of that group of cases in which the convicted had not been found to present a flight risk, danger to commit another crime, or risk to tamper with evidence/witnesses. At first glance, there seems to be no reason, in such cases, why not to temporarily stay the judgment of imprisonment. However, a comparative analysis across various jurisdictions (the paper focuses on the U.S., Canada, Germany, France, Spain, and Slovenia) shows that some of them do engage in a degree of “no-stay” policy, while one jurisdiction even makes it the only solution in practice. Given the absence of the flight risk, absence of the danger to commit another crime, and absence of the danger to temper with evidence/witnesses, what might the reason for the “no-stay” jurisprudential policy be? The paper argues that the puzzle inevitably involves a constitutional dimension. Liberty is a fundamental constitutional right and a human right. It can, of course, be limited, but not without any good or legitimate reason, and perhaps not even without a good proportionate reason. In the absence of such reasons, the practice against stays would seem groundless and unconstitutional. Examining different approaches to the issue across the different jurisdictions, the paper argues that those with more stringent “no-stays” policies run afoul of liberty as the basic constitutional and human right. However, there is nonetheless a subtle set of reasons that do explain why, in those jurisdictions with more liberal “pro-stay” policies, but not complete or automatic “pro-stay” policy, in our group of cases, some degree of “no-stay” policy may still be warranted. The paper concludes with a proposal that results from such a comparative analysis as the sound approach to this issue, advocating a degree of gradual convergence where, and to the extent that, the differences between jurisdictions clearly allow for such a due affirmation of liberty.