The trend to replace petroleum-based products with sustainable alternatives has shifted research efforts toward plant-based materials such as cellulose nanocrystals (CNCs). CNCs show promise in numerous applications (e.g., composites and rheological modifiers); however, maximizing their performance often requires surface modifications with complex chemistries and purification steps. Presented here is a novel surface modification method with the potential to tune CNC properties through the in situ deposition of cellulose phosphate oligosaccharides during CNC production. This was achieved by leveraging the selective solubility of oligosaccharides, which are soluble at a low pH (during the CNC hydrolysis) yet become insoluble and precipitate onto CNC surfaces upon increasing pH during quenching. Oligosaccharide-coated CNCs demonstrated subtle changes induding higher surface charge densities and lower water adsorption capacities and viscosities than their unmodified counterparts. CNC surface coverage was tuned by controlling the oligosaccharide degree of polymerization. Overall, this fundamental study introduces an easily scalable modification route that opens the door for expanded CNC functionality and applications.