In modern psychotherapy practice, digital tools for check-ins and self reflection increasingly supplement the therapy experience as a form of modern telehealth. These include diary card apps designed for Dialectical Behavioral Therapy (DBT), such as DBT Diary Card & Skills Coach, Simple DBT Skills Diary Card, and DBT Coach: Guided Therapy, and Cognitive Behavioral Therapy (CBT) online worksheets, such as Reflective, uMore, and ThinkCBT. Both tools aim to foster continuity of therapeutic work between sessions, promote client self‑monitoring, and inform therapist decision making. While the overall goals are similar between these two tools, their theoretical underpinnings and user experience differ considerably. For clinicians, choosing a digital tool to recommend requires balancing issues of usability, fidelity, client engagement, and clinical insight.