The adequate representation of interactions between the land surface and the atmosphere is of crucial importance in modern numerical weather prediction (NWP) systems. In this context, this study examines how errors in the planetary boundary layer (PBL) depend on the quality of near-surface prediction over land for medium-range NWP. Two series of 10-day forecasts from Environment and Climate Change Canada (ECCC)’s global deterministic prediction system were evaluated: one similar to what is currently used in ECCC’s operational systems and the other with improved land surface modeling and land data assimilation. An objective evaluation was performed for the 2019 summer season in North America, with a special emphasis on three specific areas: northern Canada, the central US, and the southeastern US. The results indicate that the impact of the new land surface package is more difficult to interpret in the PBL than it is at the screen level. The error differences between the two experiments are quite distinct for the three regions examined. As expected, random errors (standard deviations) for air temperature and specific humidity in the PBL are directly linked with their own random errors at the screen level, with correlation coefficients decreasing from a value of one at the surface to values of about 0.2–0.3 a few kilometers above the surface. Less expected, however, is the fact that random errors in the lower atmosphere also strongly depend on changes in air temperature biases at the surface. Warmer near-surface conditions lead to increased random errors for air temperature in the lower atmosphere, in association with the development of the deeper PBL, with greater spatial variability. This finding is of particular interest when evaluating new configurations of NWP systems for implementation in national meteorological and environmental prediction centers.