Remote sensing technologies are essential for monitoring crop development and improving agricultural management. This study investigates the automation of Sentinel-2 satellite data processing to enhance wheat growth monitoring and provide actionable insights for smallholder farmers. The objectives include (i) analyzing vegetation indices across phenological stages to refine crop growth monitoring and (ii) developing a cost-effective user-friendly web application for automated Sentinel-2 data processing. The methodology introduces the “Area Under the Curve” (AUC) of vegetation indices as an independent variable for yield forecasting. Among the indices examined (NDVI, EVI, GNDVI, LAI, and a newly developed RE-PAP), GNDVI and LAI emerged as the most reliable predictors of wheat yield. The findings highlight the importance of the Tillering to the Grain Filling stage in predictive modeling. The developed web application, integrating Python with Google Earth Engine, enables real-time automated crop monitoring, optimizing resource allocation, and supporting precision agriculture. While the approach demonstrates strong predictive capabilities, further research is needed to improve its generalizability. Expanding the dataset across diverse regions and incorporating machine learning and Natural Language Processing (NLP) could enhance automation, usability, and predictive accuracy.