The transition between brown dwarfs and low-mass stars is defined by the onset of hydrogen fusion in the core of an object. Current studies typically separate these objects at 80 Jupiter masses. However, this transition mass is dependent on each object’s environment and composition, with models suggesting a transition mass from 73 to 96 Jupiter masses. Here we present five companions discovered by TESS that are near this mass range transiting main sequence stars. We put them in context by exploring the properties of known transiting brown dwarfs and low-mass stars. We also discuss possible distinct characteristics for these separate populations including orbital properties as well as host star effective temperature and metallicity.