In this design case, we describe our first attempt to create a virtual mathematics tutoring program for students with learning disabilities. We describe in detail how the design was motivated by the pandemic which forced schools into remote learning, how a university and school collaborated on the design, the rationale for our design decisions, and aspects of the design that did not meet the intended outcomes. Three interrelated design failures included problems with flexible scheduling, challenges seeing students' work, and inconsistent use of a collaborative, communication tool. Pervasive to all these failures were underlying communication issues associated with being remote. We share our experience learning from and altering our design of these features for the future.