Competency-based medical education and programmatic assessment intend to increase the opportunities for meaningful feedback, yet these conversations remain elusive. By comparing resident and faculty perceptions of feedback opportunities within one internal medicine residency training program, we sought to understand whether and how principles underlying meaningful feedback could be supported or constrained across a variety of feedback opportunities. Using case-study qualitative methodology, interviews and focus groups were conducted to explore 19 internal medicine residents' and 7 faculty members' perceptions of feedback across a variety of feedback opportunities: coaching, mini-CEXs, in-training evaluation reports and routine clinical supervision. Our data analysis moved iteratively between developing conceptual understandings and fine-grained analyses, while attending to both deductive and inductive analysis. Our results suggest that all feedback opportunities, including those created through formalized assessments, can foster meaningful feedback if faculty establish a trusting relationship with the resident, base their feedback on direct observation and support resident learning. However, formalized assessments were often perceived as inhibiting the conditions for meaningful feedback. A coaching program provided a context in which meaningful feedback could arise, in part because faculty were supported in shifting their focus from patient to resident. Meaningful feedback in clinical education may be fostered across a variety of feedback opportunities, however, it is often constrained by assessment. We must consider whether increasing the frequency of formative assessments may inhibit efforts to improve our feedback cultures while, in contrast, freeing up faculty to focus on supporting resident learning could improve these cultures.