In infancy and in the early years of life, emotion regulation and attachment relationships with parents are tightly intertwined. However, whether this link persists into adolescence has not yet been established and requires exploration. This pilot study utilizes an experimental design to assess the patterns of parent-adolescent interactions that are hypothesised to be related to two specific aspects of adolescents' emotion regulation, namely: visual attention and autonomic arousal to distress and comfort stimuli. Two innovative and ecologically valid methodologies were utilized to assess (a) patterns of attachment-based parent-adolescent interactions among 39 adolescent-parent dyads from the general population, using the Goal-corrected Partnership in Adolescence Coding System (Lyons-Ruth et al. Goal corrected partnership in adolescence coding system (GPACS), 2005) applied to a conflict discussion task; (b) the two aspects of adolescent emotion regulation were assessed with the Visual/Autonomic Regulation of Emotions Assessment (VAREA) (Vulliez-Coady et al. Visual/Autonomic Regulation of Emotions Assessment, VAREA) paradigm, an attachment-related, emotionally arousing experimental procedure, using a distress-then-comfort paradigm, in conjunction to an eye-tracker synchronized with a physiological device that measured gaze and skin conductance response, (SCR), or emotional reactivity. In line with research in infancy, as predicted, markers of secure parent-adolescent interaction were linked to higher amplitude of SCR for distress and comfort pictures, and with longer attention to comfort pictures. On the other hand, parental role-confusion was associated with less time spent on comfort pictures by the adolescent. Overall, this pilot study suggests that interventions supporting collaborative communication between adolescents and their parents, as well as working to reduce parental role-confusion, may improve adaptive adolescent emotion regulation as assessed via physiological measures.