Well MSean,
Autos do not need to wind, as you mentioned in your process, just shake it a bit so it gets running enough before you wear it, adjust the time and off you go.
On the other hand, it seems that your movement could be misadjust, dry (as in no oil in it), or probably the winding gears might be stuck or broken. In any of this case, take it to your watchsmith for an inspection.
Ultimatly, ask The Zigmeister for help.
Cheers!