To describe the frequency, content, dynamics, and patterns of cost conversations in academic medical oncology across tumor types. We reviewed 529 audio recordings between May 3, 2012, to September 23, 2014, from a prospective three-site communication study in which patients at any stage of management for any solid tumor malignancy were seen in routine oncology appointments. Recordings were deidentified, transcribed, and flagged for any mention of cost. We coded encounters and used qualitative thematic analysis. Financial issues were discussed in 151 (28%) of 529 recordings. Conversations lasted shorter than 2 minutes on average. Patients/caregivers raised a majority of discussions (106 of 151), and 40% of cost concerns raised by patients/caregivers were not verbally acknowledged by clinicians. Social service referrals were made only six times. Themes from content analysis were related to insurance eligibility/process, work insecurity, cost of drugs, cost used as tool to influence medical decision making, health care-specific costs, and basic needs. Financial concerns influenced oncology work processes via test or medication coverage denials, creating paperwork for clinicians, potentially influencing patient involvement in trials, and leading to medication self-rationing or similar behaviors. Typically, financial concerns were associated with negative emotions. Financial issues were raised in approximately one in four academic oncology visits. These brief conversations were usually initiated by patients/caregivers, went frequently unaddressed by clinicians, and seemed to influence medical decision making and work processes and contribute to distress. Themes identified shed light on the kinds of gaps that must be addressed to help patients with cancer cope with the rising cost of care.