The Pacifier

The pacifier.... Genius soothing tool or bane of my existence?

My little boy loves his pacifiers. In an effort to have a child not addicted to the pacifier, I only let him suck on it when he's due for a nap or going to sleep at night. (Which is really the only time he wants it anyways.) The sucking motion is very soothing for him and usually helps him make his way to la la land. I am putting stress on the word "usually" here.

At this very moment I am engaged in one of my daily battles with the pacifier. It goes like this... I insert the pacifier. The little guys eyes immediately close and sucking begins. He appears to be sucking in his sleep for a good three minutes until A) He falls asleep and the pacifier falls out or B) He knocks the pacifier out accidentally on his own with his hands. Either way a shriek erupts out of the bassinet or crib which is followed by constant crying until I jump up and reinsert the pacifier. Usually after several rounds of this he eventually gets into a deep enough sleep to not care about the pacifier.

So... the question is.. Do I continue with this behavior or let him cry himself to sleep after a little bit. (Not going to happen in the middle of this night, but possible during the day.) Is he too young for the crying himself to sleep thing? If not, how long is too long for crying? I suppose I should go to Google on this one....