Solving word problems is challenging for many children, but particularly for those with language difficulties. The objective was to examine the nature of the challenges experienced by children with language difficulties as they solved word problems in the context of a developmental-trajectory instructional sequence. We recruited 45 third graders with (n = 17) and without (n = 28) language difficulties from public and private schools and one speech-language therapy clinic. They solved word problems with additive change and compare structures and language that was either consistent or inconsistent with the structure. The instruction was based on successive simplifications to the problems whenever the child was unable to apply a structurally appropriate strategy: removing irrelevant literal information from the problem, simplifying the text syntactically, and removing irrelevant numerical information. The performance of children with language difficulties was lower than that of the typically developing children and the simplifications did not support performance to the same extent. The presence of irrelevant numerical information was challenging, especially for children with language difficulties. Removing irrelevant information from the problem was followed by stronger performance on change problems and those with consistent language, revealing that the instructional supports were not sufficient for compare and inconsistent problems.