Methods and systems for providing dynamic messages to callers on hold are disclosed. In one such method, a telephone call is received into a queue and a first wait time is calculated which corresponds to a first estimated length of time expected to elapse before an agent is available to answer the telephone call. A plurality of message elements are assembled to create a message having a length approximately equal to the first wait time, and playback of the message is initiated. A second wait time is calculated during the playback of the message. The message is modified during playback to have a length approximately equal to the second wait time if the updated estimated length of time is different than the first estimated length of time. In various embodiments, the second wait time may be continuously calculated and the message may be continuously modified during playback.