The influence of various factors on the stability of free tryptophan was evaluated in several reaction systems. After treatment, tryptophan was measured by high performance liquid chromatography. Factors such as heating, protein, and glucose were responsible for tryptophan losses in a system undergoing Maillard browning. Hydrogen peroxide caused extensive losses while pH and light had minimal effect on tryptophan stability in solution. When the stability of tryptophan was compared to lysine and threonine during browning, threonine had the highest retention. At low water activity (0.22), tryptophan had the lowest retention (42%) while at a high water activity (0.75) lysine had the lowest retention (5%). When fortified corn tortillas were made using the typical heat treatment involved in preparation, retention of added lysine and tryptophan was 85–90%.