In Indonesian cuisine, the red Tabasco pepper holds a significant place as a commonly used ingredient. However, the cultivation of this chili variety is not without its challenges, primarily due to the volatile nature of the chili prices. Farmers often struggle with the critical decision of when to plant Tabasco peppers to optimize their yields and income. Understanding the complexities of this decision-making process in the context of varying environmental conditions is crucial. Thanks to recent advances in Internet of Things (IoT) technology, innovative systems have emerged to address these challenges.This study focuses on the development of an IoT-based solution aimed at helping farmers in precisely determining the optimal planting time for Tabasco pepper. It uses five key criteria—average temperature (°C), average humidity (%), rainfall (mm), length of sunlight (hours) and groundwater usage data (m3) to make data-driven planting decisions. The urgent need for such a system becomes evident when considering the unpredictability of climate patterns and their direct impact on crop outcomes. Using historical data from 2019, obtained from the Jakarta Provincial Government Open Data DKI, and climate data from the Meteorological Agency, Climatology, and Geophysics (BMKG), the authors have successfully developed an IoT-based prototype. This prototype employs a neural network algorithm to analyze the aforementioned criteria. The result is a reliable prediction system that boasts an impressive accuracy rate of 91.26%. By offering this level of precision in determining the ideal planting time for Tabasco pepper, the system extends invaluable support to farmers, helping them optimize their cultivation practices and navigate the uncertainties of the chili market.