Background: Young people are at heightened risk for mental health problems. Apprenticeships are common pathways into the workforce at a critical developmental period. However, in some cases the working conditions for apprentices present significant challenges to mental wellness. As apprentices are unlikely to utilize traditional services, eHealth and mHealth interventions are a useful means of delivering interventions to this group. The aim of the current paper is to: (1) qualitatively explore the utility of an existing mental health app within an apprentice population; and (2) evaluate the usability, acceptability, feasibility and preliminary efficacy of a modified version of the app (HeadGear Apprentice), designed to reduce depressive symptoms in an apprentice working population. Methods: Study One: Twenty-six apprentices (aged 18-30) took part in one of eight (90-min) focus groups. Participants explored the HeadGear app, took part in group discussions, and completed uMARS questionnaires. Modifications were made to the app based on feedback. Study Two: In the follow-up pilot testing, 47 apprentices downloaded and used the modified app over 30 days. Assessment occurred online at baseline, 5-weeks, and 3-months post-baseline. Feasibility was evaluated using consent rates, adherence and attrition. Acceptability was assessed using questionnaires and a post-study interview. Depression, anxiety, well-being, and work performance scores were used to assess preliminary efficacy. Results: Overall, the app was well-received in both studies, with high self-reported scores for acceptability and utility. However, engagement-both in terms of self-report and adherence-was an issue in both studies. In Study Two, users completed approximately one-third of the app's therapeutic content, with increased usage associated with improved outcomes. This had implications for the preliminary effectiveness of the app [depression as measured by the PHQ-9 Cohen's d = 0.27 (95%CI:-0.16-0.69)]. At follow-up users reported improvements in all outcomes, but overall only change in well-being reached statistical significance [Cohen's d = −0.29 (95%CI:-0.72-0.14)]. Deady et al. Apprentice M-Health App: Pilot Study Conclusion: Overall, findings from the two studies suggest that an eHealth tool, HeadGear Apprentice, was an acceptable and well-received intervention when adapted to young apprentices. However, questions remain regarding how to improve engagement and adherence to the program. These questions appear critical to effectiveness. The two studies also have implications for awareness raising in this population. Whilst preliminary results were encouraging, these improvements, along with a full-scale efficacy trial, are needed to better understand the utility of smartphone applications for mental health in this population. Trial registration: ACTRN12618001475235 https://www.anzctr.org.au/Trial/ Registration/TrialReview.aspx?id=375875&isReview=true.