As the recording music industry entered the digital era, significant turmoil emerged due to piracy and illegal downloading, and royalty payments to artists via streaming platforms. To date, the previous research examining the industry shift focused on consumer-based decisions such as whether to download music illegally, and, more recently, experiences with streaming services. Using sensemaking as our lens, we examine changes and challenges through in-depth interviews with music industry practitioners. The participants have been directly impacted by the digital shift in general and by specific issues such as piracy and poor compensation from streaming platforms. We develop a typology of industry members based on their development of sensemaking capabilities as they navigate the ever-changing industry and the resulting influence on market practices.