Older adults' medication planning and scheduling can benefit from collaborative support from healthcare providers, and through the use of cognitive support AIDS. In this paper, we investigate the communication strategies that older adults utilize for collaborative medication scheduling. 32 community-dwelling older adults participated in pairs, and performed the role of a patient or provider in a simulated patient-provider medicationscheduling task. Each pair worked together using an unstructured (Paper condition) or a structured (MedTable condition) medication-scheduling tool and completed two medication-scheduling problems (1 simple, 1 complex). Verbal interactions were captured and analyzed sequentially to identify the structure and content of conversation related to problem solving. Based on the study, we found that (a) MedTable likely fostered interactive communication through more turn taking during conversations, and shorter length of conversations within these turns, (b) MedTable-based conversations were symmetrically structured with 'repeat-back' conversations, potentially arising out of the fact that MedTable supported confirmatory strategies by making shared information more salient during interactions. The implications of the results for the design of medication scheduling tools for older adults are discussed.