Communicative visualizations can support multiple chart-grounded takeaways, including divergent or conflicting ones; we refer to this variation as interpretive ambiguity. Such ambiguity can undermine a visualization's communicative goal when the supported takeaways diverge from its intended message. Evaluating visualizations with target audiences can surface this variation, but such evaluations can be costly and difficult to scale. In this work, we explore persona-conditioned Vision Language Models (VLMs) as a complementary evaluation tool for interpretive ambiguity. For a given visualization, our pipeline uses topic-relevant personas to elicit candidate contextual takeaways supported by interpretations of perceived visual patterns, such as trends and clusters. We derive a Target--Pattern--Scope framework for comparing these interpretations, use LLM judges to assign Compatible, Disjoint, or Opposing ambiguity labels to statement pairs, and summarize their distribution in an ambiguity profile. To improve chart grounding, we benchmark candidate VLMs on chart comprehension and select the highest-performing model for each chart type. We evaluate statement-pair labeling against human-authored annotations and apply the approach to real-world, public-facing visualizations curated from established datasets. Through case studies, we examine how perceived visual patterns relate to contextual takeaways and how a visualization redesign changes the sampled interpretations. Our findings show how persona-conditioned VLMs can complement human feedback by generating candidate contextual takeaways and surfacing potential ambiguity for further inspection.

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