The restoration of bowel continuity following Hartmann’s Procedure (HP) has been reported hitherto with high morbidity and mortality rates. No clear guidelines exist about timing in Hartmann’s Reversal (HR), the literature data being conflicting. We have sought to investigate the effect of the interval time between HP and HR in short- and long-term HR outcomes through a retrospective study based on consecutive patients undergoing HR between 2009 and 2017 in two regional hospitals in Italy. Demographic characteristics, comorbidities, intra- and post-operative data, as well as early complications, were recorded. Long-term data were collected on the surgical site occurrences of Incisional Ventral Hernia (IVH). One hundred and five patients were recruited for the study. Late HR, female gender, and long operating time were related to the highest incidence of peri-operative complications. Patients who developed IVH had undergone HR at significantly shorter times and had a higher Body Mass Index (BMI). The timing of HR seems to be an important variable linked to the onset of early and late post-operative complications. The patients submitted to early HR show a significantly lower complication rate but, at the same time, a higher rate of IVH incidence after restorative surgery. These data, in our opinion, reflect the need for planning, where possible, an early restoration of bowel continuity after HP.