To investigate patient discomfort during archwire engagement and disengagement in patients treated with self-ligating and conventional brackets using a split-mouth design. Eighteen consecutive patients (15 female, 3 male; age: 22.2 ± 6.4 years) who requested treatment with fixed orthodontic appliances were randomly assigned for bonding with SmartClip self-ligating brackets on one side of the dentition and conventional standard edgewise brackets on the other. During the course of treatment, patients rated the discomfort experienced during every archwire engagement and disengagement using a numeric rating scale. Results were evaluated for round and rectangular nickel titanium and rectangular stainless steel, titanium molybdenum, and Elgiloy archwires. Patients also rated their overall experience retrospectively for both bracket systems. Regardless of archwire type, disengagement was rated as being significantly more painful on the SmartClip side (P = .027). For rigid, rectangular archwires, engagement and disengagement were rated as being significantly more painful on the SmartClip side (P = .031; P = .004). Retrospective ratings favored conventional brackets beyond ratings recorded during treatment. Engagement and disengagement of rigid rectangular archwires caused more pain with SmartClip self-ligating brackets than with conventional ones. Careful archwire manipulation and patience during full alignment are essential for limiting chairside pain. Low pain levels will help ensure treatment satisfaction and compliance.