The aims of this study were to compare, in vitro, the shear bond strength (SBS) of stainless steel orthodontic brackets bonded to silver amalgam with the use of three different intermediate resins and two different adhesives, and to evaluate bond failure mode. Forty-five amalgam specimens were divided into three equal groups. In groups 1 and 2, the brackets were bonded with Unite (3M Unitek) using Reliance Metal Primer (RMP; Reliance Orthodontic Products) and Power Bond OLC (PB OLC; Ortho Organizers Inc.) as intermediate resins, respectively. In group 3, Resinomer and One-Step Plus (OS+; Bisco Inc.) were used. Thirty bovine teeth served as the controls to test bracket bonding to acid-etched enamel with Unite and Resinomer-OS+. After thermocycling from 10 to 50 degrees C 1000 times, all samples were tested for SBS. Bond failure sites were classified using a modified adhesive remnant index (ARI) system. Data were analyzed with one-way analysis of variance, post hoc Tukey multiple comparison and chi-square tests. The results showed that the mean SBS to amalgam surfaces were significantly lower than those to etched bovine enamel (P<0.001). There were no statistically significant differences in mean SBS between the amalgam bonding groups (P>0.05). For the ARI, significant differences were found between the amalgam- and enamel-bonding groups (P<0.001). The mean SBS of stainless steel orthodontic brackets bonded to amalgam surfaces with RMP, PB OLC, OS+ intermediate resins and Unite and Resinomer adhesives was significantly lower than to etched bovine enamel. Bond failure occurred at the amalgam-adhesive interface regardless of the adhesive system and without damage to the amalgam restoration.