Observations show that the seasonal cycle of precipitation in parts of southern Mexico and Central America exhibits a bimodal signal, known as the Midsummer drought (MSD), but there is no consensus on which processes are most relevant for the two-peak structure of the rainy season. This paper evaluates three hypotheses that could explain the MSD: the SST cloud-radiative feedback, the solar declination angle and the Caribbean LowLevel Jet (CLLJ) moisture transport hypotheses. Model experiments produced by the Met Office Hadley Centre (MOHC) for CMIP6 as well as ERA5 reanalysis data are used to critically assess the predictions of each hypothesis. The simulations capture the double peak signal of precipitation well and reasonably simulate the spatial and temporal variations of the MSD and other relevant climate features such as the CLLJ. Evidence from our analysis suggests that the Eastern Pacific SSTs do not increase in late summer in ERA5 data and only slightly increase in the simulations. More importantly, the Eastern Pacific SST variability in ERA5 and in the model experiments cannot explain the differences in the seasonality of precipitation. The net shortwave radiation at the surface shows a two-peak seasonal cycle; however, this behaviour appears to result from a strong anti-correlation of the incoming shortwave and convective activity due to cloud radiative-effects. There was no evidence found by this study of a causal link in which absorption of shortwave energy forces precipitation variations, as suggested by the solar declination angle hypothesis. The moisture convergence, CLLJ and the precipitable water vapor variations best explain the characteristics of the observed and simulated MSD, particularly for the onset of the MSD. The diagnosed variations of moisture convergence, which are synchronous with the timing of the MSD, point to a dynamic mechanism in which the low-level inflow from the Caribbean is more important for the MSD than other radiative mechanisms.