The pathway to summertime convective precipitation remains a vexing research problem because of the nonlinear feedback between soil moisture content and the atmosphere. Understanding this feedback is important to the southeastern U. S. region, given the high productivity of the timberland area and the role of summertime convective precipitation in maintaining this productivity. Here we explore triggers of convective precipitation for a wide range of soil moisture states and air relative humidity in a mosaic landscape primarily dominated by hardwood forests, pine plantations, and abandoned old field grassland. Using half-hourly sensible heat flux, micrometeorological, hydrological time series measurements collected at adjacent HW, PP, and OF ecosystems, and a simplified mixed layer slab model, we developed a conditional sampling scheme to separate convective from nonconvective precipitation events in the observed precipitation time series. The series analyzed (2001–2004) includes some of the wettest and driest periods within the past 57 years. We found that convective precipitation events have significantly larger intensities (mean of 2.1 mm per 30 min) when compared to their nonconvective counterparts (mean of 1.1 mm per 30 min). Interestingly, the statistics of convective precipitation events, including total precipitation, mean intensity, and maximum intensity, are statistically different when convective precipitation is triggered by moist and dry soil conditions but are robust in duration. Using the data, we also showed that a “boundary line” emerges such that for a given soil moisture state, air relative humidity must exceed a defined minimum threshold before convective precipitation is realized.