My gear shifting is very rough when tranny is cold. Should I be concerned?

What is your question?

When I first start my truck and put into drive, the transmission shifts roughly from 1st to 2nd gear (not bad for any other gears, though). There also seems to be a high pitch squeal at higher RPM's in first gear, right before shifting to 2nd. However, the more I drive and the warmer the transmission gets, the shifting seems to be a lot smoother (what I would consider normal) and the squeal goes away. This has been going on for almost a year, but hasn't seemed to get any worse. Would anyone have any ideas to what is happening and any solutions before I take it in for repair?