Our study refers to the highly stretchable elastomer PDMS (polydimethylsiloxane), a material used with a wide range of applications. Its basic mechanical properties can be tuned, e.g., by varying the curing conditions; moreover, its surface properties can be tuned by modification techniques. We modified our PDMS by irradiating the samples with an excimer lamp at 172 nm. Such a treatment hardens the elastomer at the surface, and it becomes silicalike; the sample changes to a “quasi” two-layer system with a graded interface. When such samples are stretched, surface cracks occur beyond a critical strain. The increase of crack length with increasing strain is evaluated by means of video screenshots. The impact of the curing conditions is addressed by analyzing samples prepared at different cross-linking temperatures, resulting in differing bulk properties but similar surface properties. Crack length and crack velocity are evaluated with each sample based on single randomly chosen cracks. The results are discussed on the basis of theoretical concepts for channeling cracks in multilayer systems with polymeric substrates. Typically, with applications, random cracks should develop at high strain only and, if present, should propagate slowly along the surface but not into the depth of the sample. Our investigation shows that the mechanical material properties of the substrate are vital with respect to such stable cracking, rather than the surface properties. In particular, the curing conditions chosen for the substrate are essential to reduce cracking, a fact less regarded with applications so far.