Type Ia supernovae (SNe Ia) are widely believed to arise from the thermonuclear disruption of a carbon-oxygen white dwarf (WD) which has reached some instability condition due to interaction with a binary companion. Historically astronomers believed this was most like to result from steady accretion of material from a non-degenerate companion onto the WD until it reached the critical Chandrasekhar mass. A decade ago, a new rare subclass of SNe Ia with exceptionally high luminosities challenged this scenario: a handful of SNe Ia were deemed to be candidates for arising from "super-Chadrasekhar" progenitor systems exceeding (sometimes significantly) the Chandrasekhar mass. In this talk I will give an update on recent developments for this sub-class of SNe Ia, including new data from recent very nearby super-Chandra SNe Ia. I will also discuss the potential yield of super-Chandra SNe Ia in the LSST era and what this could tell us about the diversity of possible SN Ia progenitor systems.