The fact that youth widely engage with the online space in order to improve their emotional health has been lost amongst the debate surrounding adolescents' technology use and associated well-being. Two studies focused on adolescents’ use of technology to cope with stressors in daily life. Focus groups (Study 1; n = 16) indicated that youth readily identify using technology to cope and perceive it as helpful for emotional relief. Experience sampling participants (Study 2; n = 156) completed a baseline assessment of online coping and mental health and one week of reports, five times daily, on their technology use, stress, and emotions. Multilevel regression results indicated that across their daily lives, youth who widely endorsed using online strategies to cope responded more negatively to stressors and displayed difficulties in recovering from worry and jealousy. Results held even controlling for use of technology, typical number of stressors, and mental health. Findings highlight the potential shortcomings and comorbid vulnerabilities for youth who frequently turn to the online environment to seek support, information, or distraction.