Cross-linked hydrogel surfaces exhibit reduced stiffness when polymerized against polymeric hydrophobic surfaces. As such, these layers play a critical role in contact mechanics, particularly exhibiting strong relative adhesion with colloidal probes when the contact area is small. This prevents the use of continuum models of adhesive soft contact. To connect mechanisms of stretch to the force response, depth-controlled nanoindentation experiments were conducted on polyacrylamide (pAAM) hydrogel samples using colloidal probe atomic force microscopy (AFM). The pAAM sample had a high water content of >90% and was molded against polyoxymethylene (POM) to create a more dilute surface layer with thickness ∼0.5 μm. Indentations to multiple depths between 50 nm and 1.25 μm were repeated 10 times each. First, the force drops during the unloading, and separation segments of each indentation were characterized. This described the detachment progression for increasing areas of contact, revealing that the pull-off force for a single chain was in the single-pN range. Second, the stretched polymer network was modeled as an array of parallel, linear springs. Assuming a constant areal chain density of α = 100 chains/μm 2 , the maximum force of adhesion was plotted versus the volume of chains stretched upward, and the average chain stiffness was calculated from a linear fit to be 22.8 × 10 −6 N/m. A Weibull distribution analysis of detachment events revealed a dependence of chain stiffness on maximum indentation depth (d max ), with higher stiffness at shallower depths approaching k chain ≈ 20 × 10 −6 N/m. These findings on adhesion mechanics between a vanishing hydrogel surface and probe can guide the development of multifunctional hydrogels for various biomedical applications.