The reactivity of both coupling partners—the glycosyl donor and acceptor—is decisive for the outcome of a glycosylation reaction, in terms of both yield and stereoselectivity. Where the reactivity of glycosyl donors is well understood and can be controlled through manipulation of the functional/protecting‐group pattern, the reactivity of glycosyl acceptor alcohols is poorly understood. We here present an operationally simple system to gauge glycosyl acceptor reactivity, which employs two conformationally locked donors with stereoselectivity that critically depends on the reactivity of the nucleophile. A wide array of acceptors was screened and their structure–reactivity/stereoselectivity relationships established. By systematically varying the protecting groups, the reactivity of glycosyl acceptors can be adjusted to attain stereoselective cis‐glucosylations. The sweet spot: An operationally simple system to gauge glycosyl acceptor reactivity is presented that employs two conformationally locked donors with stereoselectivity that critically depends on the reactivity of the acceptor. The structure–reactivity/stereoselectivity relationships of a wide array of acceptors were established. The reactivity of glycosyl acceptors can be adjusted by systematically varying the protecting groups to attain stereoselective cis‐glucosylations.