The increasing use of digital applications in healthcare has led to a greater need for patient education materials. These materials, often in the form of pamphlets, booklets, and handouts, are designed to supplement physician–patient communication and aim to improve patient outcomes. However, the effectiveness of these materials can be hindered by variations in patient health literacy. Readability, a measure of text comprehension, is a key factor influencing how well patients understand these educational materials. While there has been growing interest in readability assessment in medicine, many studies have demonstrated that digital texts do not frequently meet the recommended sixth-to-eighth grade reading level. The purpose of this opinion article is to review readability from the perspective of studies in pediatric medicine, internal medicine, preventative medicine, and surgery. This article aims to communicate that while readability is important, it tends to not fully capture the complexity of health literacy or effective patient communication. Moreover, a promising avenue to improve readability may be in generative artificial intelligence, as there are currently limited tools with similar effectiveness.