Two experiments were conducted on alfalfa to investigate the effects of the addition of commercial chestnut hydrolyzable tannin at ensiling on 1) silage fermentation quality in lab-scale silos and protein degradation in the rumen, and 2) silage fermentation quality and proteolysis in bale silages. Wilted alfalfa was prepared with 4 tannin levels (0, 2, 4, and 6% on a dry matter (DM) basis; T0, T1, T2, T3, respectively) and ensiled in lab-scale silos. Silages (33% DM) were analyzed for fermentation quality, protein rumen degradability in situ, and organic matter digestibility in vitro through gas production after 120 d of conservation. Wilted alfalfa containing 0 and 4% tannin (T0 and T2) was harvested at 40% DM (wilting level I) and 53% DM (wilting level II) for bale (600 mm diameter) silage. Silages were analyzed for fermentation quality after 78 d of conservation. All the silages were well fermented with no butyric acid. Lab-scale silages showed reductions in ammonia, nonprotein nitrogen (NPN) and DM losses in T2 and T3 treatments, while the fermentation acid profiles were unaffected. In experiment 1, the untreated silage (T0) had the highest protein degradability after being incubated in the rumen. The addition of tannin reduced crude protein ruminal disappearance in a dose-dependent manner. However, the tannin reduced the organic matter digestibility by 5.1% for all of the tannin addition levels. The tannin positively affected the silage quality in the round bale silages, in particular reducing ammonia and NPN in the lowest wilting level. In both experiments, T2 treatment reduced proteolysis without any influence of DM on the binding reaction and reduced the NPN by 15% in comparison to the control.