Abrupt and gradual dry-off strategies by reducing feeding level (normal vs. reduced energy density), reducing milking frequency (twice vs. once daily), and administration of a dopamine agonist after last milking (i.m. saline vs. cabergoline injection) were investigated (2 × 2 × 2 factorial arrangement) for their effects on feed intake, milk yield, energy balance, milk leakage, and clinical udder characteristics in 119 Holstein cows. In the last week before dry-off, cows were assigned to 1 of 4 combinations of feeding level and milking frequency. Within 3 h after last milking, cows were injected with either saline or a dopamine agonist (cabergoline; Velactis, Ceva Santé Animale; labeled for use only with abrupt dry-off, i.e., no preceding reduction in feeding level or milking frequency before last milking). After dry-off, all cows were fed the same diet for dry cows, and data collection continued for a week. Dry matter intake (DMI) was recorded in automated feed bins and milk yield in an automatic milking system where additional concentrate was fed. Clinical udder characteristics and milk leakage were scored 10 times during the week before and the week after dry-off. Before dry-off, total DMI decreased with reduced feeding level compared with normal feeding level, but did not differ between milking frequencies. The combined effect of reduced DMI and diet energy concentration resulted in a 47% lower net energy intake with reduced feeding level compared with normal feeding level during the week before dry-off. Milk yield was approximately 30% lower during the week before dry-off when either feeding level or milking frequency was reduced compared with no change in feeding level or milking frequency, whereas milk yield was 45% lower when both feeding level and milking frequency were reduced. The net energy balance during the week before dry-off was negative with reduced feeding level and more negative when combined with twice-daily milking. After dry-off, udder engorgement was reduced in the 3 gradual dry-off treatments compared with abrupt dry-off. Cabergoline injection after last milking resulted in least udder engorgement and signs of milk leakage for 48 h, but also resulted in abrupt reduction of DMI lasting approximately 24 h irrespective of treatment before dry-off. In conclusion, gradual cessation of lactation by reducing milking frequency to once daily without reducing the feeding level decreased milk yield before dry-off in high-yielding dairy cows and reduced udder engorgement after dry-off without inducing negative energy balance during the period of dry-off. In contrast, reduced feeding level induced negative energy balance, which may compromise welfare due to metabolic stress and hunger. No clear differences in risk of milk leakage after dry-off were observed between abrupt and gradual dry-off management strategies. Use of cabergoline led to fewer signs of milk leakage and reduced udder engorgement during the first days after dry-off, which may positively affect welfare at dry-off. However, the mechanism behind and the welfare consequences of the concomitant abrupt decrease in DMI lasting approximately 24 h needs further investigation to complete our understanding of dopamine agonist use for dry-off.