Left atrial appendage occlusion is utilized as a second line therapy to long-term oral anticoagulation in appropriately selected patients with atrial fibrillation (AF). We examined the feasibility of cryoballoon (CB) pulmonary vein isolation (PVI) subsequent to Watchman device implantation. The study prospectively identified patients with Watchman devices (>90 days old) who underwent CB-PVI ablation between 2018 and 2019. Twelve consecutive patients (male 50%; mean age 71 ± 9 years; CHA₂DS₂-VASc score 3.4 ± 1.1) underwent CB-PVI procedures after Watchman device implantation (mean 182 ± 82 days). Acute PVI was achieved in 100% of patients. All patients had evidence of complete (n = 9) or partial (n = 3) endothelialization of the surface of the Watchman device with conductive tissue properties demonstrated during electrophysiologic testing. There were no major procedure-related complications including death, stroke, pericardial effusion, device dislodgment, device thrombus, or new or increasing peri-device leak. Mean peri-device leak size (45-day postimplant: 0.06 ± 0.09 mm vs Post-PVI: 0.04 ± 0.06 mm; p = 0.61) remained unchanged. Two patients had recurrence of AF after the 90-day blanking period (13.2 ± 6.6 months). One patient underwent a redo ablation procedure for recurrent AF. This pilot study suggests the potential feasibility of CB-PVI ablation in patients with chronic Watchman left atrial appendage occlusion devices. Larger prospective studies are needed to confirm the clinical efficacy and safety of this approach.