I don't think you have to worry about auto updates breaking the webtop.I'd start w/restoring the phone back to stock.Then,try these steps when starting up the LAPDOCK 500:
1) Ensure the lid on the LAPDOCK is closed
2) With the PHOTON on its lockscreen,plug it into the LAPDOCK.
3) Press the power button on the PHOTON to turn the screen off,but,leave the phone on & place in the phone cradle.
4) Open the lid & the LAPDOCK 500 should power on within 30 seconds or less.
When exiting the LAPDOCK 500,close all windows on the webtop,minimize, & do the same w/the phone.
I know these steps aren't written in any user manual(there aren't any meaningful manuals to be found,just a few basic video how-to's on MOTOROLA'S website & YOU-TUBE).
However,through trial & error,I've found these steps work in getting past the screen saver mode of the ever-floating MOTOROLA symbol.