The dynamics and recent and possible future changes of the June–September rainfall associated with the North American Monsoon (NAM) are reviewed in this chapter. Our analysis as well as previous analyses of the trend in June–September precipitation from 1948 until 2010 indicate significant precipitation increases over New Mexico and the core NAM region, and significant precipitation decreases over southwest Mexico. The trends in June–September precipitation have been forced by anomalous cyclonic circulation centered at 15°N latitude over the eastern Pacific Ocean. The anomalous cyclonic circulation is responsible for changes in the flux of moisture and the divergence of moisture flux within the core NAM region. Future climate projections using the Coupled Model Intercomparison Project Phase 5 (CMIP5) models, as part of the Intergovernmental Panel on Climate Change (IPCC) Fifth Assessment Report (AR5), support the observed analyses of a later shift in the monsoon season in the presence of increased greenhouse gas concentrations in the atmosphere under the RCP8.5 scenario. The CMIP5 models under the RCP8.5 scenario predict significant NAM-related rainfall decreases during June and July and predict significant NAM-related rainfall increases during September and October.