The beef cattle marketing structure imposes stress on calves due to weaning, transport, commingling, and adaptation to new diets, resulting in a weakened immune systems at the height of disease risk, frequently causing bovine respiratory disease. Backgrounding programs facilitate opportunities for calves to overcome stressors by building immunity, and adapting the rumen to high concentrate diets for improved feedlot performance. Four experiments were conducted to compare backgrounding strategies and effects of supplementation frequency performance and the effects of the ruminal environment. In Exp. 1, 48 weaned steers were used to investigate the effects of transportation and supplementation frequency, while in Exp. 2, 36 heifers were used to investigate only supplementation frequency. No differences in gains were observed due to transportation stress or supplementation frequency. Weaning stress resulted in elevated (P < 0.05) creatine kinase and neutrophil:lymphocyte ratios during the first week. In Exp. 3, 48 calves were used to compare the effect of tall fescue type on performance and health. Calves on novel endophyte fescue had higher ADG (P = 0.07) than on endophyte-infected fescue. Experiment 4 investigated the changes in ruminal environment due to supplementation frequency. No differences were observed between supplementation frequencies for ruminal pH, ammonia, or VFA concentration, and DM, or CP digestibility. Therefore, the rumen maintained a hospitable environment to promote bacterial protein synthesis and fiber digestion with every 48 h supplementation. Backgrounding calves with high fiber co-product supplements or on novel endophyte fescue can enhance calf performance.