Posing questions is a direct way for teachers to push students to verbalize justifications and make connections among ideas--a crucial component of giving students with learning disabilities access to high levels of mathematical reasoning--but this skill is difficult to learn. We recruited four pre-service special education teachers to provide 1-1 algebra tutoring to students with learning disabilities while receiving instruction related to posing mathematics questions and supporting students' reasoning. The pre-service teachers increased their frequency of questions overall and of questions that probed students' thinking or explored mathematical relationships. Students gave correct and complete responses to these more complex questions approximately half of the time; however, pre-service teachers most often reduced the complexity of their questions when students gave incomplete responses. The findings of this study illustrate the potential for pre-service special education teachers to develop questioning routines that engage students with learning disabilities in mathematical reasoning while scaffolding their progress toward new understanding.