Abstract We present comprehensive orbital analyses and dynamical masses for the substellar companions Gl 229 B, Gl 758 B, HD 13724 B, HD 19467 B, HD 33632 Ab, and HD 72946 B. Our dynamical fits incorporate radial velocities, relative astrometry, and, most importantly, calibrated Hipparcos-Gaia EDR3 accelerations. For HD 33632 A and HD 72946 we perform three-body fits that account for their outer stellar companions. We present new relative astrometry of Gl 229 B with Keck/NIRC2, extending its observed baseline to 25 yr. We obtain a <1% mass measurement of 71.4 ± 0.6 M _Jup for the first T dwarf Gl 229 B and a 1.2% mass measurement of its host star (0.579 ± 0.007 M _⊙) that agrees with the high-mass end of the M-dwarf mass–luminosity relation. We perform a homogeneous analysis of the host stars’ ages and use them, along with the companions’ measured masses and luminosities, to test substellar evolutionary models. Gl 229 B is the most discrepant, as models predict that an object this massive cannot cool to such a low luminosity within a Hubble time, implying that it may be an unresolved binary. The other companions are generally consistent with models, except for HD 13724 B, which has a host star activity age 3.8σ older than its substellar cooling age. Examining our results in context with other mass–age–luminosity benchmarks, we find no trend with spectral type but instead note that younger or lower-mass brown dwarfs are overluminous compared to models, while older or higher-mass brown dwarfs are underluminous. The presented mass measurements for some companions are so precise that the stellar host ages, not the masses, limit the analysis.