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Simple Summary: Tannins have traditionally been avoided in animal nutrition due to their anti-nutritive effects. However, recent studies reported hydrolysable tannins as beneficial additives that have antimutagenic, anticarcinogenic, antidiarrheal, and antiulcerogenic effects on animals. In a study testing the inclusion of hydrolysable tannins as a potential nutritive factor to reduce boar taint in entire males, significant enlargement of the parotid glands (parotidomegaly) was observed. In this study, we aimed to determine the morphological and immunohistochemical basis for the observed parotidomegaly. We discovered that enlargement of glandular lobules and acinar area, an increased ratio between the nucleus and cytoplasm of serous cells, and increased excretion of proline-rich proteins (PRPs) were characteristic of the experimental group that received the highest dietary tannin intake. The mandibular salivary gland, on the other hand, did not show significant morphological changes among the experimental groups. This suggests increased functional activity of the parotid salivary glands as the first and most important line of defense against high dietary tannin and its potential negative effects. The ingestion of hydrolysable tannins as a potential nutrient to reduce boar odor in entire males results in the significant enlargement of parotid glands (parotidomegaly). The objective of this study was to characterize the effects of different levels of hydrolysable tannins in the diet of fattening boars (n = 24) on salivary gland morphology and proline-rich protein (PRP) expression at the histological level. Four treatment groups of pigs (n = 6 per group) were fed either a control (T0) or experimental diet, where the T0 diet was supplemented with 1% (T1), 2% (T2), or 3% (T3) of the hydrolysable tannin-rich extract Farmatan®. After slaughter, the parotid and mandibular glands of the experimental pigs were harvested and dissected for staining using Goldner's Trichrome method, and immunohistochemical studies with antibodies against PRPs. Morphometric analysis was performed on microtome sections of both salivary glands, to measure the acinar area, the lobular area, the area of the secretory ductal cells, and the sizes of glandular cells and their nuclei. Histological assessment revealed that significant parotidomegaly was only present in the T3 group, based on the presence of larger glandular lobules, acinar areas, and their higher nucleus to cytoplasm ratio. The immunohistochemical method, supported by color intensity measurements, indicated significant increases in basic PRPs (PRB2) in the T3 and acidic PRPs (PRH1/2) in the T1 groups. Tannin supplementation did not affect the histo-morphological properties of the mandibular gland. This study confirms that pigs can adapt to a tannin-rich diet by making structural changes in their parotid salivary gland, indicating its higher functional activity. [ABSTRACT FROM AUTHOR]