Fluency in both the construction and interpretation of molecular structures is a critical learning objective in the second-year organic chemistry curriculum. With the introduction of PerkinElmer's ChemDraw structure drawing tool into undergraduate laboratory courses, students are challenged to develop fundamental molecular drawing skills using authentic, industry-standard software and to incorporate their submissions into a number of digital lab report assignments. Consistent exposure to ChemDraw throughout the organic laboratory curriculum augments student comprehension of organic structures as well as hones their technical skills through increasingly sophisticated assignments. By expanding their use of the program to reinforce foundational ideas of structure and reactivity, students further strengthen their knowledge of concepts such as intermolecular forces, states of matter, chromatographic principles, and reaction mechanisms. Students reported favorable experiences in their use of the program throughout the curriculum.