Numerous natural and engineering scenarios necessitate the entrapment of air pockets or bubbles on submerged surfaces. Current technologies for bubble entrapment rely on perfluorocarbon coatings, limiting their sustainability. Herein, we investigated the efficacy of doubly reentrant cavity architecture towards realizing gas-entrapping microtextured surfaces under static and dynamic pressure cycling. The effects of positive (>1 atm), negative (<1 atm), and positive–negative cycles on the stability the gas entrapment inside individual doubly reentrant cavities were studied across a range of pressures, ramp rates, intercycle intervals, and water-column heights. Remarkably, the fate of the trapped air under pressure cycling fell into either of the following regimes: the bubble (i) monotonically depleted (unstable), (ii) remained indefinitely stable (stable), or (iii) started growing (bubble growth). This hitherto unrealized richness of underwater bubble dynamics should guide the development of coating-free technologies and help us understand the curious lives of air-breathing aquatic and marine insects.