Providing video mail to and from residents of controlled-environment facilities may include presenting a resident or non-resident a user interface and receiving a selection to send video mail. Whereupon, the user may be offered a selection to either upload a video or image or to capture a video or image. A selection by the user is accepted and in response to a selection to upload a video or image file, the user may be presented a file selection interface to enter a video or image filename and/or browse for a video or image file. In response to a selection to capture a video or image, the user may be presented a video or image capture interface for capturing the video or image, such as by using a camera of the host device. The selected or recorded video or image may then be uploaded and presented to the recipient for viewing.