Mathematical problem posing was advocated as one major area needing systematic investigation. It was also recommended that school mathematics learning should involve experientially real problem situations and using handheld devices to bridge across formal and informal contexts for mathematical learning. This research study explored how 11 middle school students generated mathematical problems in a real-life setting with the help of a mobile device. The multiple case study gathered observations, participants' generated artifacts, and individual interviews and reported a number of themes related to the general process, barriers or challenges participants encountered, and the role of the hand held device.