We report the first Penning-trap mass measurements of the proton rich 101,103Sn at the Low Energy Beam and Ion Trap (LEBIT) located at the Facility for Rare Isotope Beams (FRIB). Precise mass measurements are both fundamental to understanding nuclear stability and testing theoretical predictions. Substantial interest surrounds the tin isotopic chain near the doubly-magic 100Sn isotope. Since the mass of 100Sn is currently disputed in the recent 2020 Atomic Mass Evaluation (AME2020) database, precise mass values for neighboring isotopes provide necessary anchor points for testing extrapolations toward the proton drip line. However, performing mass measurements in this region is a formidable task given that isotopes around 100Sn have very short half-lives and the reactions used to produce them have low production cross sections. As a result, the masses of both 101,103Sn were also not well-known at the time of AME2020, with 103Sn even being classified as a “seriously irregular mass” and given an extrapolated value. LEBIT's mass measurements of 101,103Sn are thus a testament to the reach of state-of-the-art radioactive ion beam facilities such as FRIB. These experimental results both well anchor the masses of connected parent isotopes and further illuminate the ongoing discrepancy in the mass of 100Sn. They additionally allowed for a comprehensive assessment of the predictive power of a recently developed Bayesian model combination (BMC) framework employing statistical machine learning to perform mass extrapolations. Excellent agreement between BMC predictions and experimental mass values in the region, including those from LEBIT, provided confidence in the extrapolations of tin masses down to the potential proton drip line nucleus 96Sn, a region of the nuclear chart that is not yet accessible in the laboratory. As experimental campaigns push closer to exotic nuclei such as 100Sn, the interplay of precise mass values with theoretical frameworks will continue to provide crucial insights into nuclear structure.