This disclosure describes techniques for providing a wireless communication device with context-based voicemail messaging. In reply to a call, a wireless communication device may select a message based on a context. As an example, a wireless communication system may detect a call directed to a wireless communication device from a caller, generate one of a plurality of reply messages for the caller based on a context of the wireless communication device derived from input information received by at least one input of the wireless communication device, and transmit the generated reply message to the caller. In some cases, the message may be selected based on both context and caller identity. In addition, the message may be selected based at least in part on analysis of a pattern of usage or user activity with respect to the wireless communication device.