Subclinical ketosis affects approximately 40% of dairy cows in North America. Current recommended treatments for ketosis focus on providing cows with more energy. However, the most effective treatments, such as oral propylene glycol, only resolve ketosis approximately 50% of the time. The objective of this research was to evaluate the effect of decreasing milking frequency from 2 milkings/day, to 1 milking/day for 2 wk in conjunction with a standard treatment of 5 d of oral propylene glycol in cows diagnosed with ketosis. Ketosis was defined as a blood β-hydroxybutyrate concentration of ≥1.2mmol/L. From November 2016 to September 2017, 104 ketotic cows from the University of Guelph Livestock Research Innovation Centre were studied. 55 cows were randomly allocated to the once/day milking group, and 49 were enrolled in the twice/day milking group. All cows inhabited the same pen during their time on trial, and all cows were milked in a DeLaval VMS robot equipped with Herd Navigator. Blood, milk, and urine samples were collected in a 21-d period to analyze ketones over time in the cows. Disease occurrence was recorded up to 60 DIM and reproductive performance, examining days to first breeding, and pregnancy on the first breeding were explored. CanWest DHI herd recording data were collected weekly, for a period of 15 wk, examining milk production, milk component data, and SCC. Results indicate that once per day milking reduced the risk of subsequent ketosis, this was determined through the use of a logistic regression model in SAS. For cows in lactation 1, the odds of ketosis for once/day milking treatment was reduced by 99% compared with those in the twice/day milking treatment group on d 18 of trial (P = 0.0005, CI: 3.38 × 10⁻⁶–0.0258). For cows in lactation 2+, the odds of ketosis for once/day milking treatment group is 0.18 times the odds of ketosis in the twice/day milking treatment group on d 18 of trial (P = 0.0002, CI: 0.0729–0.426).