Although studies have evaluated the ecotoxicity and fate of trenbolone acetate (TBA) metabolites, namely 17α-trenbolone (17α-TBOH), 17β-trenbolone (17β-TBOH), and trendione (TBO), their environmental transport processes remain poorly characterized with little information available to guide agricultural runoff management. Therefore, we evaluated TBA metabolite transport in representative agricultural systems with concurrent assessment of other manure-derived constituents. Leachate generated using manure from TBA-implanted cattle was applied to a subsurface infiltration plot (4 m) and surface vegetative filter strips (VFSs; 3, 4, and 5 m). In the subsurface experiment, 17α-TBOH leachate concentrations were 36 ng L−1 but decreased to 12 ng L−1 in initial subsurface discharge. Over 75 minutes, concentrations linearly increased to 23 ng L−1 (C/Co = 0.32–0.64). In surface experiments (n = 4), 17α-TBOH leachate concentrations ranged from 11–150 ng L−1, remained nearly constant with time, but were attenuated by ∼70–90% after VFS treatment with no statistical dependence on the VFS length. While attenuation clearly occurred, the observations of a highly mobile fraction of all constituents in both surface runoff and subsurface discharge suggest that these treatment strategies may not always be capable of achieving threshold discharge concentrations. To attain no observed adverse effect levels (NOAELs) in receiving waters, concurrent assessment of leachate concentrations and available dilution capacities can be used to guide target treatment performance levels for runoff management. Dilution is usually necessary to achieve NOAELs, and receiving waters with less than 70–100 fold dilution capacity are at the highest risk for steroidal endocrine disruption.