Pediatric obesity management strategies suffer from a high rate of dropout and persistence of weight excess, despite the use of new tools, such as automated mobile technology (MT). We aimed to compare the efficacy of two 6-month personalized MT protocols in terms of better engagement, adherence to follow-up visits and improved anthropometric and lifestyle parameters. MT contacts consisted of three personalized/not automated What’s App® self-monitoring or challenge messages per week. Messages, sent by a dedicated coach were inserted between three-monthly in-presence regular visits with (PediaFit 1.2) or without (PediaFit 1.1) monthly free-of charge short recall visits carried out by a specialized pediatric team. The sample included 103 children (mean age 10 years, range 6–14) recruited in the Pediatric Obesity Clinic between January 2017 and February 2019, randomized into Intervention group (IG) (n = 24 PediaFit 1.1; n = 30 PediaFit 1.2) and Control group (CG) (total n = 49). Controls received standard treatment only (indications for healthy nutrition and physical activity, and three months in presence regular visits). Overall, both IGs achieved significantly better results than the CGs for all considered parameters. Comparison of the two IGs at the sixth month in particular showed an IG 1.2 statistically significantly lower drop-out rate (10% vs. 62%, p = 0.00009), along with significantly improved BMI (p = 0.003), Screen Time (p = 0.04) and fruit and vegetables consumption (p = 0.02). The study suggests that the hybrid association of messaging through personalized/not automated MT plus monthly free-of charge recall visits may improve the prefixed outcomes of MT weight loss intervention programs.