The nature of silica surfaces is relevant to many chemical systems, including heterogeneous catalysis and chromatographies utilizing functionalized-silica stationary phases. Surface linkages must be robust to achieve wide and reliable applicability. However, silyl ether silica support linkages are known to-be susceptible to detachment when exposed to: basic conditions. We use single-molecule spectroscopy to examine the rate of surface linkage failure upon exposure to base at a variety of deposition conditions. Kinetic analysis elucidates the role of thermal annealing and addition of blocking layers in increasing stability. Critically, it was found that successful surface modification strategies alter:the rate at which base molecules approach the silica surface as opposed to reducing surface linkage reactivity: Our results also demonstrate that the innate structural diversity of the silica: surface is likely the cause of observed heterogeneity in surface-linkage disruption kinetics.