Generative optimization uses large language models (LLMs) to iteratively improve artifacts (such as code, workflows or prompts) using execution feedback. It is a promising approach to building self-improving agents, yet in practice remains brittle: despite active research, only 9% of surveyed agents used any automated optimization. We argue that this brittleness arises because, to set up a learning loop, an engineer must make "hidden" design choices: What can the optimizer edit and what is the ``right'' learning evidence to provide at each update? We investigate three factors that affect most applications: the starting artifact, the credit horizon for execution traces, and batching trials and errors into learning evidence. Through case studies in MLAgentBench, Atari, and BigBench Extra Hard, we find that these design decisions can determine whether generative optimization succeeds, yet they are rarely made explicit in prior work. Different starting artifacts determine which solutions are reachable in MLAgentBench, truncated traces can still improve Atari agents, and larger minibatches do not monotonically improve generalization on BBEH. We then study these factors jointly in harness optimization on TBLite, evaluated on Terminal-Bench 2.0. We also propose a batch-size and credit-horizon rule that, calibrated on TBLite, transfers to DeepSWE after adjusting to its token costs and comes within 1% of the best configuration tested at each context budget.

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