An extended earthquake swarm occurred beneath southeastern Long Valley Caldera between May and November 2014, culminating in three magnitude 3.5 earthquakes and 1145 cataloged events on 26 September alone. The swarm produced the most prolific seismicity in the caldera since a major unrest episode in 1997–1998. To gain insight into the physics controlling swarm evolution, we used large‐scale cross correlation between waveforms of cataloged earthquakes and continuous data, producing precise locations for 8494 events, more than 2.5 times the routine catalog. We also estimated magnitudes for 18,634 events (~5.5 times the routine catalog), using a principal component fit to measure waveform amplitudes relative to cataloged events. This expanded and relocated catalog reveals multiple episodes of pronounced hypocenter expansion and migration on a collection of neighboring faults. Given the rapid migration and alignment of hypocenters on narrow faults, we infer that activity was initiated and sustained by an evolving fluid pressure transient with a low‐viscosity fluid, likely composed primarily of water and CO2 exsolved from underlying magma. Although both updip and downdip migration were observed within the swarm, downdip activity ceased shortly after activation, while updip activity persisted for weeks at moderate levels. Strongly migrating, single‐fault episodes within the larger swarm exhibited a higher proportion of larger earthquakes (lower Gutenberg‐Richter b value), which may have been facilitated by fluid pressure confined in two dimensions within the fault zone. In contrast, the later swarm activity occurred on an increasingly diffuse collection of smaller faults, with a much higher b value.