Transdermal healthcare systems have gained significant attention for their painless and convenient drug administration, as well as their ability to detect biomarkers promptly. However, the skin barrier limits the candidates of biomolecules that can be transported, and reliance on simple diffusion poses a bottleneck for personalized diagnosis and treatment. Consequently, recent advancements in transdermal transport technologies have evolved toward active methods based on external energy sources. Multiple combinations of these technologies have also shown promise for increasing therapeutic effectiveness and diagnostic accuracy as delivery efficiency is maximized. Furthermore, wearable healthcare platforms are being developed in diverse aspects for patient convenience, safety, and on‐demand treatment. Herein, a comprehensive overview of active transdermal delivery technologies is provided, highlighting the combination‐based diagnostics, therapeutics, and theragnostics, along with the latest trends in platform advancements. This offers insights into the potential applications of next‐generation wearable transdermal medical devices for personalized autonomous healthcare.