Aminosilanes were protected with benzyloxylcarbonyl succinimidyl ester (CBZ-SE) in solution, forming carbamates. Investigations of surface assemblies made of CBZ-protected aminosilanes were done using XPS, contact angle measurements, and an amine reactive fluorescent probe. Spontaneous loss of the protection group was observed and determined to be caused by the catalytic effect of silanols from both the surface and the assembling silanes. The use of CBZ-protected monoalkoxy, which require days to assemble, as opposed to di- and trialkoxy silanes which require only hours, mitigated the deprotection.