Online mental health services offer programs and resources for users to better manage their mental health, where part of the process of engaging in these services involves initiatives that attempt to motivate a transition from online to face-to-face support. What can we make of those initiatives through the insight of users? This research, platforming the voices of young adults aged 18–25 years, provides valuable insights into the unique help-seeking experiences of this demographic and the effectiveness of online mental health services in facilitating a transition to face-to-face support. Using an online survey comprising of open-response and Likert scale questions, 101 participants provided qualitative and quantitative feedback. Key quantitative findings revealed 66% of participants had transitioned from online mental health services to face-to-face supports following their initial engagement. Moreover, a substantial 57.05% of participants expressed satisfaction with their online experiences. Mental health education pages were the most accessed resource by service users, with 82.18% of participants having used them. Emerging from a series of 10-point Likert scale questions, “contact with a professional” (7.58) and “receiving a referral” (9.25) were the highest rated predictors of transition, while barriers such as a “lack of motivation” and “bureaucratic complexities” were identified from qualitative data as the dominant inhibiting factors. Lastly, psychoeducation emerged as a crucial tool for empowering participants toward overcoming stigma, with the theme of trust highlighted as the most critical factor in determining the confidence of young adults attempting to transition from online to face-to-face support.