Cured pork loins are sausages with a production tradition in several regions worldwide. They are made from one of the noblest cuts of pork, and for this reason cured loins are one of the most expensive pork meat products. Establishing the correct shelf life allows products to be accepted by the consumer, and to avoid the costs associated with shorter shelf lives. The aim of this study is: (1) to establish proper shelf life by evaluating the willingness of participants to consume and the sensory modifications that occur during prolonged storage via Check All That Apply (CATA) questions; and (2) to study the behavior of Listeria monocytogenes through a microbial challenge test. Sliced cured pork loins can be stored at 6 ± 1 °C for 105 days while maintaining a consumer acceptance of more than 75%. The freshness loss was associated mainly with a decrease in aromatic notes (particularly the smoke and cured aroma), and with the appearance of spoiled characteristics, specifically a sour/vinegar aroma and acidic taste that were detected by a reduced proportion of participants. The freshness evaluation was positively influenced by the typical characteristics of cured products, such as color and a garlic and wine aroma. Sour/vinegar aroma and acidic taste were the attributes most associated with higher freshness penalization. During the period of the test, Listeria monocytogenes inoculated onto the cured loin slices did not grow.