Serendipity is an engaging, deeply personal and even magical experience to some. While serendipity has been noted to arise during people's interactions with digital photos, we have yet to understand how this occurs or how it could be supported during-and-through the use of technology. Inspired by findings about serendipity arising from people's shuffle listening, we designed a digital photo display system to explore how we could support people's encounters with serendipity with digital photos. Through this, we gained a deeper understanding of this technology-mediated serendipity and found ways that can support and even nudge people towards encountering serendipity.