Background and Objectives: The prognostic impact of ventricular fibrillation (VF) recurrences after a successful shock in out-of-hospital cardiac arrest (OOHCA) is still poorly understood, and some evidence suggests a potential pro-arrhythmic effect of chest compressions in this setting. In the present analysis, we looked at the short-term and long-term prognosis of VF recurrences in OOHCA. And their potential association with chest compressions. Materials and Methods: The Progetto Vita, prospectively collecting data on all resuscitation efforts in the Piacenza province (Italy), was used for the present analysis. From the 461 OOHCAs found in a shockable rhythm, only those with optimal ECG tracings and good audio recordings (160) were assessed. Rhythms other than VF post-shock were analyzed five seconds after shock delivery and survival to hospital admission, hospital discharge, and long-term survival data over a 14-year follow-up were collected. Results: Population mean age was 64.4 ± 16.9 years, and 31.9% of all patients were female. Mean time to EMS arrival was 5.9 ± 4.5 min. Short- and long-term survival without neurological impairment were higher in patients without VF recurrence when compared to patients with VF recurrence, independently from the pre-induction rhythm (p < 0.001). After shock delivery, VF recurrence was higher when chest compressions were resumed early after discharge and more vigorously. Conclusions: VF recurrences after a shock could worsen short and long-term survival. The potential pro-arrhythmic effect of chest compressions should be factored in when considering the real risks and benefits of this procedure.