When deciding on the voluntary waiting period of an individual cow, it might be useful to have insight into the persistency for the remainder of that lactation at the moment of the insemination decision, especially for farmers who consider persistency in their reproduction management. Currently, breeding values for persistency are calculated for dairy cows but, to our knowledge, prediction models to accurately predict persistency at different moments of insemination are lacking. This study aimed to predict lactation persistency for DIM 305 at different insemination moments (DIM 50, 75, 100, and 125). Available cow and herd level data from 2005 to 2022 were collected for a total of 20,508 cows from 85 herds located in the Netherlands and Belgium. Lactation curve characteristics were estimated for every daily record using the data up to and including that day. Persistency was defined as the number of days it takes for the milk production to decrease by half during the declining stage of lactation, and calculated from the estimated lactation curve characteristic ‘decay’. Four linear regression models for each of the selected insemination moment were built separately to predict decay at DIM 305 (decay-305). Independent variables included the lactation curve characteristics at the selected insemination moment, daily milk yield, age, calving season, parity group and other herd variables. The average decay-305 of primiparous cows was lower than that of multiparous cows (1.55 *10−3 vs. 2.41*10−3, equivalent to a persistency of 447 vs. 288 days, respectively). Results showed that our models had limitations in accurately predicting persistency, although predictions improved slightly at later insemination moments, with R2 values ranging between 0.27 and 0.41. It can thus be concluded that, based only on cow and herd milk production information, accurate prediction of persistency for DIM 305 is not feasible.