Emerging clinical guidelines recommend shared decision making to individualize drug regimens for older adults with Type 2 diabetes mellitus. While the current health education campaign for diabetes in the United States recommends physician-initiated medication-related discussions about adherence and side effects, little emphasis is placed on soliciting patient concerns. This study's aim was to explore the concerns of older adults with diabetes about the complexity of their drug regimens and to determine whether they discussed medication-related concerns with their physician. Twenty-two patients with Type 2 diabetes age 65 years and older who used five or more medications were selected from an urban academic geriatric medicine practice in the United States. In-depth semi-structured interviews were conducted to uncover participants' perceptions of multiple medication use and related discussions with providers. The predominant theme that emerged was the variability in medication-related topics that patients perceived they could discuss with their physician. While most participants described physician-initiated discussions about adherence and side effects, many did not bring up concerns about medication cost or their desire to reduce medication burden. In order to encourage greater patient involvement in medication decision making for diabetes treatment, educational messages promoting patient-physician dialogue need to take more account of patient concerns.