The goal of the study was to understand how pre-service and preschool teachers understand and use the mathematical symbols <, >, and = when comparing figures and shapes of different sizes and thicknesses. Using both quantitative and qualitative methods, we examined a study population of 71 pre-service teachers attending a course for teaching mathematics to pre-schoolers and 149 preschool teachers. Our results show that the majority of participants did not answer the questions correctly, with a significant difference between how the two groups validated their answers, indicating that the participants do not correctly understand that mathematical symbols should (<, >, and =) only be used in the mathematical context.