We present photometric and spectroscopic observations of the unusual Type Ia supernova ASASSN-18tb, including a series of SALT spectra obtained over the course of nearly six months and the first observations of a supernova by the Transiting Exoplanet Survey Satellite (TESS). We confirm a previous observation by Kollmeier et al. (2019) showing that ASASSN-18tb is the first relatively normal Type Ia supernova to exhibit clear broad (∼ 1000 km s −1 ) Hα emission in its nebular phase spectra. We find that this event is best explained as a sub-Chandrasekhar mass explosion producing M N i ≈ 0.3 M . Despite the strong Hα signature at late times, we find that the early rise of the supernova shows no evidence for deviations from a single-component power-law and is best fit with a moderately shallow power-law of index 1.69 ± 0.04. We find that the Hα luminosity remains approximately constant after its initial detection at phase +37 d, and that the Hα velocity evolution does not trace that of the Fe III λ4660 emission. These suggest that the Hα emission arises from a circumstellar medium (CSM) rather than swept up material from a non-degenerate companion. However, ASASSN-18tb is strikingly different from other known CSM-interacting Type Ia supernovae in a number of significant ways. Those objects typically show an Hα luminosity two orders of magnitude higher than what is seen in ASASSN-18tb, pushing them away from the empirical light curve relations that define "normal" Type Ia supernovae. Conversely, ASASSN-18tb exhibits a fairly typical light curve and luminosity for an underluminous or transitional SN Ia, with M R ≈ −18.1 mag. Moreover, ASASSN-18tb is the only SN Ia showing Hα from CSM interaction to be discovered in an early-type galaxy.