Prescribing cascades, where a medication is used to treat the side effect of another medication, contribute to polypharmacy and related morbidity. Little is known about clinicians' and patients' experiences with prescribing cascades. In this study, we explored why and how prescribing cascades occur across a variety of care settings and how they are managed. This descriptive qualitative study employed semi-structured interviews with older adults who may have experienced a prescribing cascade(s), their caregivers, and healthcare providers. Interviewees were recruited through physician referral from a Geriatric Day Hospital, two long-term care homes in Ottawa, Ontario, and through self-referral across Ontario, Canada. An inductive approach was used to code data and determine themes. Thirty-one interviews were conducted for ten unique patient cases. Some interviewees were involved in more than one case, resulting in 22 unique interviewees. Three themes were identified. First, recognition of prescribing cascades is linked to awareness of medication side effects. Second, investigation and management of prescribing cascades is simultaneous and iterative (rather than linear and sequential). Third, prevention of prescribing cascades requires intentional strategies to help people anticipate and recognize medication side effects. Difficulty with recruitment from both long-term care homes and through self-referral was the central limitation. This exemplifies challenges associated with studying a poorly recognized and underexplored phenomenon. In order to better recognize, investigate and manage prescribing cascades, clinicians and patients need to know more about medication side effects; they need to ask 'can this be caused by a drug?' when signs and symptoms arise or worsen; and they need access to information about medication experiences to have benefit-risk discussions and make decisions about deprescribing. Approaches for raising public awareness of prescribing cascades should be trialed to raise the profile of this issue and facilitate continued exploration of the phenomenon.