Statistics for teacher evaluations in seated and online classes show a glaring difference in both quantitative and qualitative scores. The generalized analysis of the quantitative and qualitative elements of the same course, instructor, assignment as grouped by learning environment provide an opportunity to inform future practice. In this four-year study at a small, private Midwestern university (n = 316 students over 20 course sections), the seated students were much more engaged and satisfied as demonstrated by their response rates, Likert-scale ratings of course and professor, and associated comments. Reflection and best practices were employed in the online course for continuous improvement, but the numeric values for online evaluations remained consistently and significantly lower in mean value. This study concludes with a series of takeaways for enhancing connections with students and increasing their associated evaluation scores.