The goal of machine milking is to harvest high quality milk from cows as gently, quickly, and completely as possible. Gentleness implies that the impact on teat canal, teat tissue, and teat skin must be minimized. Milking speed can be measured in several ways including milking unit-on time of individual milking observations or parlor performance. Parlor performance indicators include the number of cows milked per hour or the amount of milk harvested per stall per hour. To optimize both measures of milking speed, the time that the teat cup is attached to the cow’s teat should be kept as short as possible. The term completely describes the attempt to minimize the amount of milk that remains in the mammary gland after milking.Advancements in milking machine technologies and research enhancing our understanding of the physiological requirements of the cow over the last decades have led to optimization of the milk harvesting process. However, it is unclear which milking strategies have the potential to optimize teat tissue condition while enhancing milking performance in high-producing dairy cows with a thrice-daily milking schedule. In addition, we are lacking diagnostic techniques to reliably assess machine milking-induced changes in teat blood circulation. Such knowledge could further the understanding of how the blood circulation is affected by current machine milking practices and how they are related to the susceptibility to intramammary infection and milking performance. The objectives therefore were to (1) investigate the effect of 2 different premilking stimulation regimens on milking performance and teat tissue condition, (2) study the effect of 2 different automatic cluster remover settings on milking performance, teat tissue condition, and udder health, and (3) develop, evaluate, and employ a diagnostic technique using power Doppler ultrasonography to assess changes in teat blood flow that are associated with premilking stimulation and machine milking. Cows that were forestripped during premilking udder preparation had shorter milking unit-on time and spent less time below 1 kg/min milk flow rate to harvest the same amount of milk per milking session. The odds of machine milking-induced short-term changes to the teat tissue were lower for cows that received forestripping compared with cows that were not forestripped. Increasing the automatic cluster remover settings from 0.8 to 1.2 kg/min decreased individual milking duration and alleviated milking-machine-induced short-term changes to the teat tissue condition without adversely affecting the amount of milk harvested, milk component yields, or udder health. No meaningful differences were detected in machine-milking-induced long-term changes between treatment groups. Power Doppler ultrasonography was shown to be a suitable tool to quantify teat blood circulation in dairy cows. Teat blood flow, as assessed with power Doppler ultrasonography was associated with premilking teat stimulation and machine milking. Overall, optimization of milking routine and machine settings by means of premilking udder stimulation and modification of machine settings enhanced milking efficiency and improved teat tissue condition of dairy cows without adversely affecting their milk production or udder health indicators. Application of power Doppler ultrasonography can further our understanding of the circulatory system of dairy cows’ teats including inherent circulatory regulation mechanisms and extrinsic factors such as machine milking.