Visual persuasion uses images to shape cognition, emotion, and behavior, with its effects depending on both visual attributes and semantic context. Despite recent progress, it remains unclear whether Vision-Language Models (VLMs) understand visual persuasiveness. This motivates us to ask: can VLMs assess whether an image persuasively supports an intended message, which visual factors shape this judgment, and do they align with human judgments? Through empirical analyses on image-message pairs where human raters consistently agree on the persuasiveness judgment, we show that VLMs exhibit a recall-oriented bias: they over-predict images as persuasive while achieving high recall. We introduce Visual Persuasive Factors (VPFs), a taxonomy informed by cognitive psychology for quantifying visual cues that shape persuasive judgments. Our factor-level analysis reveals that VPFs distinguish human persuasiveness judgments, whereas VLMs only partially reproduce these patterns, often generating false positives by treating persuasion-relevant cues as sufficient evidence. Building on this insight, we evaluate VPF-guided interventions and find that properly framed VPF knowledge can improve performance, but merely specifying visual cues or adding step-by-step reasoning is insufficient. By analyzing model rationales at the level of functional reasoning steps, we further identify a central bottleneck in connecting object identification to semantic message alignment.

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