Health-care systems seek to advance their care to adolescents through the online provision of information and support. An online, moderated, asynchronous discussion board called Let’s Chat Pain was created to recruit adolescent users of online content for pain to a discussion about pain coping and associated Internet use. Participants were asked about everyday pain coping and the role they judge online information to play in this coping. They were asked about determinations of website reliability and validity for health but especially for help with pain problems. Themes around adolescent trust in online websites for pain and research are explored, in addition to inhibiting and disinhibiting factors associated with the Internet use for health. We found users to mistrust online content even when they know it to be valid. Further study is needed to assess if there are ways of instilling confidence in pain information presented online for this group.