Background/Objectives: Twiddler’s syndrome is an uncommon but clinically important complication of implantable cardiac devices, in which generator rotation within the pocket results in lead torsion, lead retraction, and device malfunction. Recurrence can necessitate repeated surgical intervention and may be preventable through early risk identification and procedural strategies. Methods: We describe a single-centre case series of three female patients with pacemaker-associated Twiddler’s syndrome. Clinical presentation, timing of lead retraction, management strategies (including pocket location and fixation approach), recurrence, and follow-up outcomes were reviewed. Results: All patients were older women and developed symptomatic device failure early after implantation, with radiographic confirmation of lead retraction and coiling occurring within three weeks in all cases. Recurrence was observed when enhanced preventive measures were not employed. Notably, in one patient, recurrence occurred after an initial revision in a second prepectoral pocket, prompting subsequent reimplantation in a subpectoral location with reinforced fixation and structured patient and family counselling, after which no further recurrence occurred at one year. In the remaining cases, revision with reinforced generator fixation and counselling was associated with stable lead position and satisfactory device function during follow-up. Conclusions: Twiddler’s syndrome most commonly presents in the first weeks following implantation. Proactive identification of at-risk patients and consideration of reinforced fixation and pocket strategies at the index procedure may reduce recurrence and avoid repeat interventions.