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Pressure-sensitive adhesives based on silicone materials have emerging potential as adhesives in healthcare products, in particular for gentle skin adhesives. To this end, adhesion to rough skin and biocompatibility are crucial factors for a successful implementation. In this study, the mechanical, adhesive, and biological properties of the two-component poly(dimethylsiloxane) Soft Skin Adhesive MG 7-9800 (SSA, Dow Corning) have been investigated and compared to Sylgard 184. Different mixing ratios of SSA's components allow for tuning of the shear modulus, thereby modifying the adhesive properties of the polymer. To give a comprehensive insight, the authors have analyzed the interplay between pull-off stress, adhesion energy, and stretch of the adhesive films on smooth and rough surfaces. The focus is placed on the effects of substrate roughness and on low pressure oxygen plasma treatment of the adhesive films. SSA shows superior biocompatibility in in vitro cell culture experiments. High pull-off stresses in the range of 3 N cm−2 on a rough surface are achieved, promising broad application spectra for SSA-based healthcare products.