Perennial grain crops have been suggested as a more sustainable alternative to annual crops. Yet their water use and how they are impacted by environmental conditions have been seldom compared to those of annual crops and grasslands. Here, we identify the dominant mechanisms driving evapotranspiration (ET), and how they change with environmental conditions in a perennial Kernza crop (US-KLS), an annual crop field (US-ARM), a C4 grassland (US-KON), and a mixed C3/C4 grassland (US-KFS) in the Central US. More specifically, we have utilized the omega (Ω) decoupling factor, which reflects the dominant mechanisms responsible for the evapotranspiration (ET) of the canopy. Our results showed that the US-ARM site was the most coupled with the lowest decoupling values. We also observed differences in coupling mechanism variables, showing more sensitivity to the water fluctuation variables as opposed to the radiative flux variables. All of the sites showed their lowest Ω value in 2012, the year of the severe drought in the Central US. The 2012 results further indicate the dependence on the water fluctuation variables. This was especially true with the perennial Kernza crop, which displayed much higher soil moisture values. In this regard, we believe that the ability of perennial Kernza to resist water stress and retain higher soil moisture values is both a result of its deeper roots, in addition to its higher Ω value. Through the analysis of both the site comparison and the comparison of the differences in years, we conclude that the perennial Kernza crop (US-KLS) is more similar in its microclimate effects to the C4 (US-KON) and mixed C3/C4 (US-KFS) grassland sites as opposed to its annual counterpart (US-ARM). This has implications for the role of perennial agriculture for addressing agricultural resilience under changing climate conditions.