The purpose of this study was to evaluate the in vitro diffusion of commercial bleaching products (hydrogen peroxide (HP) or carbamide peroxide (CP) based) with different application protocols. Human enamel-dentin discs were obtained and divided into 20 groups. Four commercial products based on HP (Pola Office+(PO), Perfect Bleach (PB), Norblanc Office-automix (NO), and Boost (BT)), and one based on CP (PolaDay CP (PD)), were evaluated with different application protocols (3 applications × 10 min or 1 application × 30 min, with or without light activation). Artificial pulp chambers with 100 µL of a buffer solution were prepared. After each application, the buffer was removed and diffused HP was quantified by fluorimetry. Data were analyzed with two-way analysis of variance (ANOVA) and Tukey’s test. In groups where 3 × 10 min applications were done, after the first 10 min, PB, NO, and PD showed similar diffusion (p < 0.05). After the second and third applications, diffusion proved similar for PO and PD, while PB exhibited the greatest diffusion. In the 30 min application groups, PO and BT showed no significant differences (p > 0.05), with similar results for NO and PD. Comparing products with or without light activation, PO, BT, and PB showed significantly greater diffusion with light activation (p < 0.05). Reapplication, and light activation, increased HP diffusion independently of the concentration of the product.