Anestrus is a major reproduction problem in pasture-based dairy operations that results in poorer reproductive outcomes than herdmates detected in estrus before the start of the seasonal breeding program. The objective of the current study was to assess a combined progesterone and estradiol benzoate treatment program including resynchrony with no treatment. Anestrous pasture-fed dairy cattle (n = 756) in 9 herds were blocked by herd and age and assigned within sequentially presented pairs of cows to be treated with an intravaginal progesterone-releasing insert for 8 d plus 2 mg of estradiol benzoate injected i.m. at insert insertion and 1 mg of estradiol benzoate injected 1 d after insert removal (d -1). Those cows detected in estrus from 0 to 3 d had a used progester-one-releasing insert reinserted for 6 d commencing on d 16 with 0.5 mg of estradiol benzoate injected i.m. 1 d after insert removal (treatment). The other cow within the pair was left as an untreated control (control). Treatment increased the risk of insemination and pregnancy by 28 d into the breeding program and resulted in conception 15 d earlier compared with controls. In contrast, treatment did not increase the risk of pregnancy after 56 d into the breeding program or at the end of the breeding season. It is concluded that treatment of anestrous dairy cattle with progesterone and estradiol benzoate combined with reinsertion of the progesterone insert resulted in earlier conception, but no difference in the final pregnancy rate compared with no treatment.