Screen use pervades daily life, shaping work, leisure, and social connections while raising concerns for digital wellbeing. Yet, reducing screen time alone risks oversimplifying technology’s role and neglecting its potential for meaningful engagement. We posit self-awareness—reflecting on one’s digital behavior—as a critical pathway to digital wellbeing. We developed WellScreen, a lightweight probe that scaffolds daily reflection by asking people to estimate and report smartphone use. In a two-week deployment with college students (\(\mathtt {N}\)=25) focused on generating formative insights, we examined how discrepancies between estimated and actual usage shaped digital awareness and wellbeing. Participants often underestimated productivity and social media while overestimating entertainment app use. They showed a 10% improvement in positive affect, rating WellScreen as moderately useful. Interviews revealed that structured reflection supported recognition of patterns, adjustment of expectations, and more intentional engagement with technology. Our findings highlight the promise of lightweight reflective interventions for supporting self-awareness and intentional digital engagement, offering implications for designing digital wellbeing tools.