Abstract Objectives This study aims to evaluate shear bond strength (SBS) of orthodontic brackets to enamel after resin infiltration pretreatment using different adhesive systems. Materials and Methods Sixty extracted maxillary first premolars were divided into five groups (n = 12). Group I: sound enamel + Transbond XT; group II: resin-infiltrated enamel (ICON) + Transbond XT; group III: ICON + Scotchbond Universal Plus; group IV: ICON + Assure PLUS; group V: ICON + Transbond Plus Self Etching. The SBS was measured using universal testing machine and analyzed using analysis of variance (ANOVA). The adhesive remnant index (ARI) score after debonding was determined under stereomicroscope with a 10× magnification. Statistical Analysis A one-way ANOVA and post hoc Tukey's test were used to compare the data. Further, the ARI scores were evaluated using a chi-squared test. The level of significance was set at p = 0.05. Results SBS of group I, II, III, IV, and V were 11.70 ± 3.17, 11.23 ± 3.06, 9.52 ± 1.73, 8.97 ± 1.12, and 9.14 ± 0.70 MPa, respectively. SBS of group IV and V was significantly lower than group I and II (p < 0.05). There was no significant difference in the ARI scores among the five groups (p > 0.05). Conclusion The SBS of enamel resin infiltration pretreatment depends on the adhesive system. The SBS of all groups was within adequate SBS range in clinical use. The most common ARI score was 2, which indicated lower risk of enamel fractures when debonding.