The suggestion to reboot everything is a good one, something else to try is pray some contact cleaner on both the connection on you phone and on the dock. A friend of mine couldn't get her iphone to work in her dock and I figured out that her iphone jacket was keeping it from seating properly on the dock. I personally from a trouble shooting stand point would not upgrade the phone, you are only adding one more element to the process.
Good Luck and let us know the outcome.
Good Luck and let us know the outcome.