Checkboxes are critical in real-world document processing where the presence or absence of ticks directly informs data extraction and decision-making processes. Yet, despite the strong performance of Large Vision and Language Models across a wide range of tasks, they struggle with interpreting checkable content. This challenge becomes particularly pressing in industries where a single overlooked checkbox may lead to costly regulatory or contractual oversights. To address this gap, we introduce the CheckboxQA dataset, a targeted resource designed to evaluate and improve model performance on checkbox-related tasks. It reveals the limitations of current models and serves as a valuable tool for advancing document comprehension systems, with significant implications for applications in sectors such as legal tech and finance. The dataset is publicly available at: https://github.com/Snowflake-Labs/CheckboxQA