A method for providing file-based media on hold (MOH) services in a Voice over Internet Protocol (VoIP) system includes selecting an MOH file and streaming digital content of the MOH file to a communication device while a call is on hold. If the call is removed from hold and placed back on hold a second time, the digital content of the MOH file is streamed to the communication device while the call is on hold the second time. The digital content is streamed from substantially a beginning of the MOH file to a first stopping point while the call is on hold the first time, and from substantially the first stopping point to a second stopping point while the call is on hold the second time.