Abstract: Deepfake detectors remain vulnerable to transfer-based black-box attacks, in which adversarial examples are generated on a source surrogate model and transferred to a target model, unknown to the attacker. Yet how source--target compatibility shapes attack success remains poorly understood. Prior studies evaluate limited detector pools and rarely disentangle architectural from training factors. We conduct a controlled evaluation of adversarial transferability across 60 detectors spanning six backbones, two pretraining regimes, and five training-data configurations, using two attack procedures: AutoAttack (AA) and the Carlini--Wagner attack with Expectation over Transformation (CW--EOT). Matched comparisons reveal significantly higher transfer when source and target share an exact backbone, architecture family, pretraining regime, or training data. This compatibility structure is attack-dependent: exact backbone compatibility has the largest effect under AA, whereas shared pretraining and training data have the largest effects under CW--EOT. When transfer is averaged across non-target sources, mean attack success rate (ASR) is $7.21\%$ under AA and $19.52\%$ under CW--EOT. By contrast, a multi-source oracle combining both attacks attains a \(64.48\%\) mean ASR after excluding exact backbone and training-data matches, showing that source averaging can substantially understate target vulnerability. We release 240,000 adversarially perturbed images, complete pairwise transfer results, detector configurations, and evaluation code. These findings establish source--target compatibility and source-model selection as central dimensions of credible transfer-based black-box robustness evaluation.