How big would Mercury need to be to retain an atmosphere? How close could Venus orbit the Sun before its atmosphere erodes away? Are habitable Earth-like atmospheres possible around the smallest stars? The growing population of rocky exoplanets with atmospheric constraints from Spitzer and JWST are beginning to provide insights on what environments permit terrestrial planet atmospheres to thrive. In this talk, I present a simple new probabilistic model for a boundary between planets with and without atmospheres, considering both the strong dependence of drivers for atmospheric loss on stellar type and the charming, complicated, crinkly, chaotic fuzziness of planets’ diverse individual life histories. I use this model to make predictions for the what the large JWST Rocky Worlds program may see and suggestions for where we astronomers might best search for life around exoplanets in the decades to come.