The widespread adoption of digital technology devices has introduced unique challenges to modern parenthood, especially during the COVID-19 pandemic when parents relied on digital technology more than ever before. Parents have experienced significant challenges during the COVID-19 pandemic, with mothers being especially vulnerable to stress and mental health problems. This study investigates associations between technology distraction of mothers while spending time with their offspring, psychological well-being (stress sensitivity), and parenting behaviors (warmth and indifference) during the COVID-19 pandemic. Mothers (n = 246) of adolescents (aged 13–18) who attended public secondary schools in Italy completed an online survey during the fourth wave of COVID-19. The pattern of associations was analyzed via path analysis. COVID-19 pandemic-induced stressors were positively associated with perceived stress, which was positively associated with technology distraction of mothers when spending time with their offspring. Furthermore, maternal technology distraction was positively associated with indifference and negatively associated with warmth. Perceived stress was negatively associated only with warmth. Strategies to mitigate stress during times of crisis and adversity might be useful for potentially vulnerable targets (e.g., mothers living with offspring during the COVID-19 pandemic). Information and prevention actions should be focused on how parents use digital devices while with their offspring.