Background: Food insecurity disproportionately affects the U.S. Latine population—particularly households with children—as measured by the USDA’s Household Food Security Survey Module (FSSM). This survey tool was originally developed among rural white women, but has since been translated into Spanish for use with Spanish-speaking households for national monitoring purposes. Though commonly used in this way, the FSSM has never undergone formal cognitive interviewing and may not fully capture the food insecurity (FI) experiences of U.S. Latine households, particularly those with children. Objective: The objective of this community-based qualitative study was to use cognitive interviewing to explore how U.S. Latine caregivers understood, interpreted, and responded to FSSM survey items and how well quantitative FSSM responses captured participants’ self-reported FI experiences. Methods: Trained student researchers conducted in-depth, semi-structured, exploratory cognitive interviews with rural, urban, and suburban Latine caregivers (n = 62) experiencing varying degrees of FI in three states—California, New York, and Texas. The three-site research team used qualitative analysis to compare FSSM items to cognitive interviewing data on item interpretation, patterns of responses, and emic perspectives. In addition to exploring item-by-item responses, the team identified cross-cutting emergent themes. Results: Participants stated that FSSM items were clear and rarely reported translation problems. However, some participants indicated being confused by items and suggested wording changes. Emergent themes across multiple items suggested that quantitative FSSM responses may underestimate FI. First, some participants responded “Never” to questions about not having enough money for food due to reliance on food assistance programs and food pantries. In addition, FSSM items about adults reducing or skipping meals appeared to be interpreted as either double-barreled or emotionally difficult, as some participants answered “Never” to these items but then described eating significantly less. Last, the FSSM’s limited response options did not appear to reflect participants’ experiences, contributing to differences between the current FSSM responses and the nuanced explanations participants shared when asked. Conclusions: FSSM validity could be improved by including items capturing strategies used for coping with FI and by providing more acceptable response options that reflect the cultural and personal experiences of U.S. Latine caregivers.