Sugar reduction in low‐moisture cookies is a challenge for the baking industry, because detrimental gluten development and starch gelatinization/pasting increase as sugar concentration decreases. In this study, sucrose and two healthful carbohydrate oligomers (i.e., isomaltulose and Mylose 351 syrup/Glucodry 314 powder) were used to explore the effects of the sucrose alternatives on results from solvent retention capacity (SRC), differential scanning calorimetry (DSC), rapid viscoanalysis (RVA), and AACC International wire‐cut cookie baking. Wheat flour SRC results indicated lower swelling of solvent‐accessible arabinoxylans in isomaltulose solution, but higher swelling in Glucodry 314 and Mylose 351 solutions, compared with that in sucrose solution. DSC and RVA results showed retardation of wheat flour starch gelatinization and pasting onset, respectively, both in the order water < Glucodry 314 ≤ Mylose 351 < sucrose ≤ isomaltulose. Isomaltulose, when predissolved, exhibited cookie‐baking responses similar to those for sucrose, suggesting that this sugar could be used successfully as a sucrose alternative to produce wire‐cut cookies with lower glycemic impact. Cookie baking with blends of sucrose and Glucodry 314 alleviated a cookie‐geometry issue observed for 100% sucrose replacement by Glucodry 314, suggesting that Glucodry 314 or Mylose 351 could partially replace sucrose for sugar‐reduction purposes.