Speech intelligibility performance with an in-the-ear microphone embedded in a custom-molded deep-insertion earplug was compared with results obtained using a free-field microphone. Intelligibility differences between microphones were further analyzed to assess whether reduced intelligibility was specific to certain sound classes. 36 participants completed the Modified Rhyme Test using recordings made with each microphone. While speech intelligibility for both microphones was highly accurate, intelligibility with the free-field microphone was significantly better than with the in-the-ear microphone. There were significant effects of place and manner of sound production. Significant differences in recognition among specific phonemes were also revealed. Implications included modifying the in-the-ear microphone to transmit more high frequency energy. Use of the in-the-ear microphone was limited by significant loss of high-frequency energy of the speech signal which resulted in reduced intelligibility for some sounds; however, the in-the-ear microphone is a promising technology for effective communication in military environments.