Disclosed herein are systems, methods, and computer-readable storage media for processing a message received from a user to determine whether an estimate of intelligibility is below an intelligibility threshold. The method includes recognizing a portion of a user's message that contains the one or more expected utterances from a critical information list, calculating an estimate of intelligibility for the recognized portion of the user's message that contains the one or more expected utterances, and prompting the user to repeat at least the recognized portion of the user's message if the calculated estimate of intelligibility for the recognized portion of the user's message is below an intelligibility threshold. In one aspect, the method further includes prompting the user to repeat at least a portion of the message if any of a measured speech level and a measured signal-to-noise ratio of the user's message are determined to be below their respective thresholds.