Oral propranolol (OP) demonstrated high efficacy and safety profile for treatment of critical infantile hemangiomas (IHs). Our aim was to assess the morphologic changes of IHs with standard and high-resolution video dermoscopy (HRVD) from baseline to 18 months either in presence or absence of OP therapy; to investigate if extended anamnestic perinatal data and clinical-dermoscopic characteristics of the IHs can correlate with therapeutic outcome. We enrolled 94 patients (112 IHs): 58 were treated with OP, 35 (42 IHs) for 6 months (group 1), and 23 (25 IHs) for 12-months (group 2); 36 (45 IHs) were followed-up. Clinical-dermoscopic examinations were performed every 3 months during therapy and follow-up. Among 67 treated IHs, superficial and deep IHs with homogenous clinical-dermoscopic aspect developed after the 2 weeks of life achieved the better outcome, stable at 9-month follow-up, independently form treatment duration. Under HRVD, glomerular vessels were prevalent at baseline; corckscrew, comma, and linear-irregular vessels were the prevalent pattern at 1, 3, and 6 months of therapy, respectively. At 12-month follow-up, adequate healing was achieved by 96% of IHs in group 2 and by 78% in group 1, showing dotted vessels. Persistent IHs displayed a reticulated aspect and linear irregular vessels, while arborizing vessels characterized relapsed IHs. A 12-month OP therapy can be considered for newborns presenting with nonhomogenous mixed IHs >3 cm on the perineal area/ lower extremities. In conclusion, HRVD allows a real time monitoring of vascular changes in IHs treated with OP and can support physicians in identifying relapses before they become clinically evident.