Some researchers have noted that /u/ in modern Midwestern American English (MAE) seems to deviate from past documentations of the vowel, but none have conducted acoustic analyses that specifically target /u/ in MAE. I conducted a survey to examine how /u/ surfaces when produced by native Midwestern speakers. I used recordings that I obtained from native Midwestern speakers reading a word list that I designed to test /u/ in a variety of phonetic environments. Using Praat and acoustic analysis techniques, I compared the F2 values produced for various test words to expected F2 values for monophthong /u/. I found widespread surface realizations that were diphthongal rather than monophthongal. Factors such as age, gender, and individual language history are taken into account to see if any of these influence how the vowel surfaces. This project considers two possible theories to account for this phenomenon: historical processes beginning in Middle English, or a relatively new vowel shift. I examine the data collected from my speakers from both of these possible theoretical perspectives, and discuss the potential consequences and questions that positing either theory as the motivator of the diphthongization creates