Originally Posted by texashoser

While you can certainly ask the gate-checked item to be transferred to a connecting flight, the ramp agents are used to grabbing everything with a gate-check tag and bringing it up to the jetway. My advice would be to do a simple gate check for the first leg, get the stroller at the jetway, and then lug it to the connecting flight (where you will do another gate check).

This is what we do when traveling with our two young children.