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Background: Among many deleterious effects on the well-being of children and youth, the COVID-19 pandemic contributed to a surge in youth mental health distress. This, coupled with pre-existing prolonged wait times for mental health care, highlighted the need for accessible community-based mental health supports. The Healthy Living Project (HELP) is a virtual lifestyle change support program aimed at promoting positive lifestyle changes and improved mental well-being among youth with mental distress. A pilot feasibility study explored youth engagement with HELP e-resources, and preliminary mental health and lifestyle measures over a 3-month period. Methods: Youth were enrolled in a 3-month pilot of the HELP e-resource. Feasibility metrics (recruitment, retention, and platform engagement) were documented, while exploratory self-reported data on emotional and behavioral difficulties, youth quality of life, sedentary behavior (screen time), sleep hygiene, and physical activity were assessed at baseline and 3 months. Results: Twenty-three youth (mean age 15.7 years, SD 1.7) completed baseline assessments and started the intervention, with ten participants retained by the end of the study. Compared with non-completers (n = 13), study completers (n = 10) tended to report higher quality of life and healthier habits (lower screen time, improved sleep hygiene, and higher activity). Ongoing access to HELP over 3 months was associated with suggestive trends toward improvement in emotional and behavioral difficulties and sleep hygiene. Engaged participants who received screen time education tended to report lower screen times as compared to unengaged counterparts. Conclusions: This study provides early insights into the implementation and acceptability of HELP e-resources among youth experiencing mental distress, with suggestive trends toward potential benefit. Low recruitment and high attrition preclude definitive conclusions, and the findings should be interpreted as exploratory. Lessons from this pilot will inform the design of a subsequent trial to more rigorously evaluate feasibility and the potential impact of HELP on youth with mental distress.