Matching insulin injection timing with meals remains a challenge for individuals with insulin-treated diabetes (ITD) using multiple daily injections (MDI). Suboptimal timing may worsen postprandial glucose dynamics. Digital insulin-support devices such as connected insulin pen caps may enhance adherence and timing accuracy. This collaborative study between Primary Care and Endocrinology evaluated the clinical impact of using a connected insulin pen cap (Insulclock® v2.0) in real-world settings.To assess whether the use of Insulclock® v2.0 improves: Injection timing relative to meals, CGM-based metabolic outcomes, and Patient-reported treatment experience.A pragmatic multicenter, prospective, open-label observational study was conducted including a run-in week, a masked two-week phase, and a four-week active feedback phase. Injection timing and CGM metrics were automatically recorded. Meal events and rapid-acting insulin doses were analyzed using ROC methodology. Treatment satisfaction was measured using ITSQ and DTSQ questionnaires.Fifty-two participants were included (mean age 54.4 years; 56.6% women; 60.4% T1D; mean baseline HbA1c 7.91%). Sites included three hospitals and one Primary Care center. Comparing masked vs active phase: GMI: 8.1 → 7.8% (p=0.034) TIR (70–180 mg/dL): +5.0% (p=0.0054) TBR (<70 mg/dL): –0.74% (p=0.0015) TAR (>180 mg/dL): –5.3% (p=0.016) On-time injections improved from 45.5% to 54.4% (p=0.0017), and timing shifted from +5.6 minutes post-meal to –5.9 minutes pre-meal (p=0.023). ITSQ and DTSQ scores indicated reduced treatment burden.The integration of a connected insulin pen cap into routine diabetes care resulted in clinically meaningful improvements in insulin administration behavior and CGM outcomes. The shift toward pre-meal timing suggests behavioral change facilitated by digital feedback. Improvements occurred across both Primary Care and Endocrinology settings, demonstrating feasibility, scalability, and value in multidisciplinary diabetes management. These findings support the role of digital adherence tools as complementary strategies to optimize MDI-based therapy.Insulclock® v2.0 improved insulin timing and glycemic outcomes while reducing perceived treatment burden in real-world practice.