Glycans are vital in biological processes, but their nontemplated, heterogeneous structures complicate structure‐function analyses. Glycosylation, the key reaction in synthetic glycochemistry, remains not entirely predictable due to its complex mechanism and the need for protecting groups that impact reaction outcomes. This concept highlights recent advancements in glycochemistry and emphasizes the integration of digital tools, including automation, computational modelling, and data management, to improve carbohydrate synthesis and support further progress in the field.