Advancements in reproductive technologies have improved pregnancy rates in postpartum cows; however, undesirable consequences leading to reduced fertility still occur. Thus, the objectives were to determine if presence of a corpus luteum (CL) at the start of estrous synchronization (AIM1) or if the length of proestrus (interval from progesterone removal to a GnRH-induced LH surge; AIM2) alters fixed timed artificial insemination (FTAI) pregnancy rates. Cycling postpartum cows (n = 285) at two locations were synchronized using the CO-Synch+CIDR® FTAI protocol. Ultrasonographic measurements of luteal area were recorded at CIDR insertion. To determine the impact of proestrus length, cows were randomly assigned to either undergo CIDR removal at the time of PGF2a injection (long proestrus, n = 145), or CIDR removal 24 hours post PGF2a injection (short proestrus, n = 140). Blood samples were collected at CIDR insertion and at insemination for progesterone (P4) analysis. Pregnancy status to FTAI was assessed using ultrasonographic diagnosis at 30 d post insemination. Data were analyzed using a MIXED procedure of SAS and examined for effects of length of proestrus, P4 concentration, luteal area, sire, location, and age. Statistical significance was determined at P 0.05) pregnancy rates. Pregnancy rates were greater in cows with >1 ng/mL P4 compared to cows with 0.05). Cows > 4 y old had higher AI pregnancy rates compared to 2–3 y cows (70.2±7.4 vs. 51±5.8%, respectively; P > 0.05). Based on these data, incorporating a presynchronization program to ensure the presence of a functional CL at the start of a FTAI protocol may improve pregnancy success in postpartum beef cows.