This award account attempts to define the status of automated carbohydrate synthesis and its applications while trying to identify areas critical for further development. In this context the work of the Seeberger laboratory over the past 10 years is reviewed. Advances and shortcomings of the first automated oligosaccharide synthesizer platform will be discussed. Using this method, access to a multitude of complex oligosaccharides has been accelerated more than 100-fold. The synthesis of usable quantities of oligosaccharides has given rise to tools that had been common-place in nucleic acid and protein biochemistry. Carbohydrate microarrays are a versatile screening platform, and affinity columns and labeled carbohydrates are beginning to aid glycobiologists. While much has been achieved, many questions remain before a generally applicable set of tools will be available to facilitate carbohydrate research much in the same way oligonucleotide and peptide biology is explored today. Application of this technology to synthetic carbohydrate antigens in synthetic vaccine candidates against parasites and bacteria is attractive and has already yielded important insights.