ABSTRACT With the Keck I Low-Resolution Imaging Spectrometer we have observed nine white dwarf candidates in the very rich open cluster NGC 2099 (M37). The spectroscopy shows seven to be DA white dwarfs, one to be a DB white dwarf, and one to be a DZ white dwarf. Three of these DA white dwarfs are consistent with singly evolved cluster membership: an ultramassive (1.28 − 0.08 + 0.05 ?> M ⊙ ?> ) and two intermediate-mass (0.70 and 0.75 M ⊙ ?> ) white dwarfs. Analysis of their cooling ages allows us to calculate their progenitor masses and establish new constraints on the initial–final mass relation. The intermediate-mass white dwarfs are in strong agreement with previous work over this mass regime. The ultramassive white dwarf has V = 24.5, ∼2 mag fainter than the other two remnants. The spectrum of this star has lower quality, so the derived stellar properties (e.g., T eff ?> , log g) have uncertainties that are several times higher than the brighter counterparts. We measure these uncertainties and establish the star’s final mass as the highest-mass white dwarf discovered thus far in a cluster, but we are unable to calculate its progenitor mass because at this high mass and cooler T eff ?> its inferred cooling age is highly sensitive to its mass. At the highest temperatures, however, this sensitivity of cooling age to an ultramassive white dwarf’s mass is only moderate. This demonstrates that future investigations of the upper-mass end of the initial–final mass relation must identify massive, newly formed white dwarfs (i.e., in young clusters with ages 50–150 Myr).