Methods for estimating playback time and handling a cumulative playback time permission are provided. In one embodiment, a file is streamed from a first device to a second device for playback. The amount of data of the file that was streamed to the second device is determined, and a playback time of the file is estimated using a time rate associated with the file and the determined amount of data of the file that was streamed to the second device. If the file is associated with a permission specifying an allowed cumulative playback time of the file, the estimated playback time can be accrued against the allowed cumulative playback time. Other embodiments are disclosed, and each of the embodiments described herein can be used alone or in combination with one another.