The tensile strength of loess, a key mechanical parameter for crack-related failures, has not received much attention in previous research, with the literature demonstrating a lack of systematic studies. Therefore, in this study, the variations in the tensile strength, crack distribution, crack number, and internal stress of an undisturbed loess were studied in detail by combining the unconfined penetration test (UPT) and a discrete element method (DEM)-based simulation. The tensile strengths of undisturbed loess samples with different height-diameter ratios (1, 1.5, and 2) were investigated by using the UPT with loading plates of different diameters (12.86 mm, 15.56 mm, and 19.02 mm). DEM simulation was then conducted based on the experimental results. The results showed that (1) the tensile strength of undisturbed loess decreased with increased height-diameter ratio, while it increased with an increase in the diameters of the loading plates; (2) the DEM simulation allowed us to study the tensile characteristics of the undisturbed loess, and the simulated tensile strengths obtained via DEM simulation agreed with those determined via the UPT; (3) the distribution of internal stress and crack number in the DEM model were significantly influenced by the height-diameter ratio and loading plate diameter; (4) the number of cracks in the DEM model increased with an increase in the diameter of the loading plate, while the number of cracks first increased and then decreased with an increase in the height-diameter ratio. This study helps us to understand the variation in the tensile strengths of undisturbed loess samples from both macroscopic and microscopic perspectives. It is expected to serve as a reference for design, construction, and maintenance in engineering projects hinging upon the Loess Plateau region in China.