As state-of-the-art machine translation models saturate standard benchmarks, the field needs more challenging evaluations to distinguish between models of varying quality. We propose augmenting existing benchmarks to increase translation difficulty by combining adversarial optimization with a differentiable translation difficulty estimator. Our Adversarial Translation Optimization (ATO) uses gradients from a combined difficulty and fluency objective to iteratively replace tokens. Because each step branches over candidate substitutions at every position, optimization becomes a tree search problem, which we address with Beam Search. ATO offers a gradient-based alternative to LLM-based dataset creation without LLM prompting, expensive human curation, or task-specific model training. Our ATO-modified benchmark lowers average translation quality (xCOMET) from 0.93 to 0.82, compared to 0.88 for paraphrasing and 0.86 for a zero-shot baseline. Through human evaluation we confirm that the modified texts remain reasonably natural while being substantially harder to translate. We release two datasets of 200 English texts each, generated by our methods, as well as the code.