This is rather an "issue" with RR. Used to be RR would Tell Winamp to PLAY, Immediately PAUSE, set the "resume" position and then tell to PLAY again -- this provided PERFECT resume effects. But It was determined that such process did NOT work in many computers, and therefore a "prevention" procedure was put in place. Now RR waits for Winamp to start propperly responding to it's commands and requests before trying to set the position of the song -- that's what you're experiencing. You can easily try a different winamp version OR try the winamp resume plugin (I don't know anything about it, but I know some people use it). As a last note, the problem you're describing ONLY happens on the same machines where the "perfect" resume seems to NOT work propperly.