This Field Notes dossier—made up of four conversations between musicians, scholars, and music fans—is meant to offer several opportunities to think through the relationship between popular music and digitality. For the longest time, it seemed the greatest investment in distinguishing between “analog” and “digital” in the field of music was made by critics and audiophiles granting a certain metaphysical cachet to the quality of analog recording in audio playback. And, of course, in the early days of the internet, when peer-to-peer sharing of MP3s was facilitated by apps such as Napster, there was tremendous discussion around the terms of distribution for copyrighted music in digital format. Today, our digital music ecology is marked by commercial streaming services and conflicts of interoperability; user-generated content creation and sync licensing for social media; and machine learning algorithms that compose music by way of text prompts in a matter of seconds. All the while networked social relations struggle against a deepening sense of isolation, catastrophe, and precarity in the world. This dossier touches on some of these themes alongside more long-standing concerns in music and culture—rhythm as both sonic and social phenomena; how connection through music helps humans navigate mental illness; and “groove” as a form of feeling and feeling of form. In it, you will find musicologist Nathan Hesselink interviewing legendary rock drummer and music producer Stan Lynch on the rise of click tracks, drum machines, and the impact of automation on the liveness of musicianship; myself interviewing Brooklyn-based house music DJ and producer Ian Friday on how digitization shaped dance music and DJ culture in New York City in the 1990s and early 2000s; scholars Lauren O’Hagan and Michael Lydon in conversation about finding community in the online legacy and musical fandom of Irish rock and blues musician Rory Gallagher; and my Field Notes co-editor Jonathan Leal interviewing Project.JDM about his wildly viral sound and motion art, the computational challenge of transcribing fractional tempos and note values, and how platforms’ proprietary algorithms inspire both financial stability and copycat theft. Much love and gratitude to all the contributors.