Abstract To achieve effective transdermal delivery, it is crucial to overcome the stratum corneum (ST) barrier and maintain high delivery efficiency even on curved, moist, and dynamically moving skin. In response, transdermal delivery technologies have evolved to integrate external stimuli with skin adhesive patch systems. However, conventional approaches frequently depend on painful needle‐based injections or cumbersome electronic devices. Furthermore, most adhesive skin patches exhibit limited transdermal delivery efficiency and suboptimal adhesion, particularly under dynamic skin conditions, thereby constraining their practical applicability. In this study, a hyaluronic acid (HA)‐loaded double‐layered suction cup (HA@d‐SC) is presented with an internal dome structure, inspired by the suckers of octopuses, to enhance transdermal delivery under dynamic skin conditions. The internal dome increases the skin contact area, ensuring robust adhesion and temporarily deforming the ST to facilitate efficient HA delivery. HA@d‐SC is fabricated using a rapid and precise inkjet printing based liquid loading platform, maintaining consistent delivery and adhesion even under challenging conditions such as vertical application and mechanical vibration. Furthermore, clinical trials demonstrate its potential to improve skin conditions without causing irritation. These findings suggest that HA@d‐SC can serve as a versatile platform for therapeutic applications, extending beyond cosmetics when combined with other bioactive agents.