The mechanisms and timescales associated with the triggering of caldera-forming eruptions remain ambiguous and poorly constrained. Do such eruptions start vigorously, then escalate, or can there be episodicity? Are they triggered through internal processes (e.g. recharge, buoyancy), or can external modulations play an important role? Key to answering these questions is the ability to reconstruct the state of the magma body immediately prior to eruption. My dissertation research seeks to answer these questions through detailed investigation of four voluminous caldera-forming eruptions: (1) 650 km3, 0.767 Ma Bishop Tuff, Long Valley, (2) 530 km3, 25.4 ka Oruanui eruption, Taupo, (3) 2,500 km3, 2.08 Ma Huckleberry Ridge Tuff, Yellowstone and (4) 250 km3, 26.91 Ma Cebolla Creek Tuff, Colorado. The main techniques I applied integrated glass geochemistry (major, trace and volatile), diffusion modeling, and detailed field sampling. In chapters two, three, and four these methods are applied to the initial fall deposits of three supereruptions (Bishop, Oruanui and Huckleberry Ridge) that preserve field-evidence for different opening behaviors. These behaviors range from continuous deposition of fall deposits and ignimbrite (Bishop), to repetitive start/stop behavior, with time breaks between eruptive episodes on the order of weeks to months (Oruanui, Huckleberry Ridge). To reconstruct the timescales of opening activity and relate this to conduit processes, I used two methods that exploit diffusion of volatiles through minerals and melt, providing estimates for the rate at which magmas ascended to the surface. This knowledge is then integrated with the pre-eruptive configuration of the magma body, based on melt inclusion chemistry, to interpret what triggered these systems into unrest. Finally, in chapter five I take a different approach by integrating geochemical data for melt inclusions and phenocryst minerals to test whether the mechanism of heat and volatile recharge often called upon to trigger crystal-rich dacitic magmas (the so-called monotonous intermediates), is applicable to the Cebolla Creek Tuff. This dissertation includes both previously published and unpublished co-authored material, and three online supplementary excel files.