Nitrogen (N) fertilization is an effective tool in sustaining crop production and the economic viability of farming systems. Depending on the soil, management practices, and climate, a significant portion of the applied N to crops is lost to the environment in the form of ammonia (NH3) volatilization, nitrate (NO3-) leaching, nitrous oxide (N2O) emissions, and dinitrogen gas (N2) losses. Nitrification inhibitors (NIs) can mitigate these losses by stabilizing N as NH4+. While early fall urea application with NIs has been studied, the effectiveness of NIs applied late in fall and their persistence into spring remains uncertain. This study involved three field experiments conducted in southern Manitoba from 2020 to 2022 to assess whether applying nitrapyrin or pronitridine in late fall with anhydrous ammonia (AA, 82-0-0) at 80% of the recommended N rate could effectively delay nitrification into spring and influence the yield and N uptake of spring-sown crops compared to AA applied at 80% and 100% of the recommended N rate without NIs. Results indicated that late fall-applied AA with the NIs, nitrapyrin, or pronitridine, did not significantly (p > 0.05) delay nitrification, resulting in no significant NH4+ stabilization. However, trends suggested slight reductions in NO3- appearance on band locations and movement between band locations. There were no significant differences in agronomic yield and crop N uptake among the treatments. A laboratory study was also conducted using urea ammonium nitrate (UAN, 28-0-0) to compare the effectiveness of different NIs across varying soil textures. In this laboratory experiment, nitrapyrin significantly (p < 0.05) inhibited nitrification in sand but had limited effectiveness in loam and clay soils. Dicyandiamide (DCD) slightly reduced nitrification (p < 0.05) only in the sand on days 14 and 21 of the experiment. However, 3,4-dimethylpyrazole phosphate (DMPP) and pronitridine, at the concentrations used, were not effective (p < 0.05) in reducing nitrification in the soils examined. Overall, the results underscore the limited effectiveness of NIs in spring from late fall-applied AA due to delayed banding operations until the soil has cooled and the variable effectiveness among nitrification inhibitor types in soils.