This chapter examines two tech sector-led online interventions—the Counter Conversations (CC) project and the Search Redirect (SR) initiative—as case studies in platform-based P/CVE strategic communications efforts. Both projects illustrate how digital tools, algorithms, and direct messaging functionalities can be harnessed to steer potentially vulnerable online users away from extremist content and toward counternarrative materials. Yet these efforts highlight significant challenges in achieving sustained and verifiable behaviour change. The CC project employs a one-to-one messaging approach on Facebook/Meta platforms, attempting to engage users identified as “at-risk” of adopting extremist beliefs. Google’s SR method uses algorithmic ad placement to divert users searching for extremist content toward curated counternarrative playlists. While this approach potentially disrupts the otherwise linear path of “radicalising” information consumption, it is hindered by similar constraints on reliable measurement, user intentionality, and long-term effect sustainability. The chapter discusses how these methodologies struggle to address underlying socialisation processes that shape both online and offline identity formation. Comparing the CC and SR initiatives with offline one-to-one interventions highlights that while scaled and data-driven, online tools remain limited by the complexity of radicalisation as a social phenomenon. The chapter’s analysis, grounded in the Reasoned Action Model and socialisation theory, suggests that practical digital P/CVE efforts require more integrated and longitudinal strategies, combining narrative credibility, meaningful engagement, and a nuanced grasp of contextual social drivers.