Despite both being outbursts of luminous blue variables (LBVs), SN 2009ip and UGC 2773 OT2009-1 have very different progenitors, spectra, circumstellar environments, and possibly physical mechanisms that generated the outbursts. From pre-eruption Hubble Space Telescope images, we determine that SN 2009ip and UGC 2773 OT2009-1 have initial masses of≳ 60 and≳ 25 M☉, respectively. Optical spectroscopy shows that at peak, SN 2009ip had a 10,000 K photosphere and its spectrum was dominated by narrow H Balmer emission, similar to classical LBV giant outbursts, also known as" supernova impostors." The spectra of UGC 2773 OT2009-1, which also have narrow Hα emission, are dominated by a forest of absorption lines, similar to an F-type supergiant. Blueshifted absorption lines corresponding to ejecta at a velocity of 2000–7000 km s− 1 are present in later spectra of SN 2009ip—an unprecedented observation for LBV outbursts, indicating that the event was the result of a supersonic explosion rather than a subsonic outburst. The velocity of the absorption lines increases between two epochs, suggesting that there were two explosions in rapid succession. A rapid fading and rebrightening event concurrent with the onset of the high-velocity absorption lines is consistent with the double-explosion model. A near-infrared excess is present in the spectra and photometry of UGC 2773 OT2009-1 that is consistent with∼ 2100 K dust emission. We compare the properties of these two events and place them in the context of other known massive star outbursts such as η Car, NGC 300 OT2008-1, and SN 2008S. This qualitative analysis suggests that massive star outbursts have many physical differences that can manifest as the different observables seen in these two interesting objects.