There are fundamental questions that teachers should ask themselves and their students as they prepare lessons on calculating area. Area measurement is commonly used in everyday life (perhaps to carpet a room or organize a space) and plays a foundational role in mathematics from multiplication all way up to calculus. Despite the usefulness of area in both life and mathematics, students often struggle to develop a conceptual meaning of area, and their only take away from lessons is often the formula for a rectangle, (length times width). This may be in part because of how textbooks structure area lessons. A recent textbook analysis study found that several popular textbooks exhibited conceptual limitations when first presenting area. Although textbooks are only one small component of the instructional process, such limitations call attention to the need for teachers to fill in some of the gaps in area measurement. The authors of this article propose that one effective way of addressing these concerns is through the modification of existing textbook tasks. Modification of tasks allows teachers to work within the boundaries of curricular materials while still providing opportunities for students to grow and explore in a variety of ways.