Twenty-five years ago, Harvard University was in the early stages of a project to build a first-generation digital library infrastructure. The project was carefully named the Library Digital Initiative (LDI), signifying that ‘digital’ would be an integral and integrated aspect of ‘library’ and not a separate entity. The initiative aimed to develop knowledge and expertise relating to digital objects, as well as technical infrastructure to create, curate, access and preserve them, and to integrate the new digital collections with Harvard’s extensive tangible collections. Today, we still benefit from the foresight of this first-generation development and the subsequent ones it spawned, but we are also at a pivotal point of reflecting on lessons learned and opportunities to be seized as we rebuild and reimagine our digital infrastructure and services in a vastly expanded data ecosystem. Predicting what libraries will look like two decades ahead is always conjecture. What we do know, however, is that while the themes and challenges from the past two decades endure, the way we are tackling them is different. This paper examines what has changed since early library digital initiatives, and the imperatives we see for the future.