Moving from conventional (CMS) to automatic (AMS) milking systems could impact milk quality. Moreover, the type and preservation methods of the forages used in the total mixed ration (TMR) (such as alfalfa hay -HTMR- or corn silage -STMR-) have been demonstrated to modify milk composition. Thus, this study investigated the effect of implementing AMS and different diet forage types on the quality of Italian Holstein-Friesian bulk milk. Milk samples (n = 168) were collected monthly from 21 commercial farms in northern Italy during a period of 8 mo. Farms were categorized into 4 groups according to their milking system (CMS vs AMS) and diet's forage type (HTMR vs STMR). Milk quality data were analyzed through the mixed procedure for repeated measurement of SAS with the milking system, diet's forage type, and sampling day as fixed effects. Milking through the AMS led to lower milk fat, freezing point and β-lactoglobulin A, longer coagulation time, and higher K content, pH and β-lactoglobulin B than CMS. Cows fed STMR produced milk with greater fat, protein, casein, Mg content, titratable acidity and β-lactoglobulin A, while reduced curd firming time, freezing point and β-lactoglobulin B than those fed with HTMR. In conclusion, milk quality is not only altered by the diet's forage type and characteristics but also by the milking system.