Okay, Here's the problem...
Whenever I have my iPod locked for a certain amount of time the volume will always drop down to one square less than half.
While this happened in Winterboard I was using Volume Boost 3.1.2 and using the Alarm Clock app.
I'm not sure if they are relevant to the problem though.
I turned off volume boost but I do not need it locked for that long since I'm outside and really desperate to find a solution.