I made it all the way through check in and tsa to the gate to board the plan with my luggage and they told me it was too large and needed to be checked since it would not fit in the overhang as my carry on. They tied a pink tag to it and had me leave it at the jet way before I boarded the plane but no one told me anything about it after that, just gave me my tag and when I went to my layover at JFK and baggage claim because that's where I thought it would be since I don't ever check bags and no one told me those bags go to the jet way for pick up baggage claim told me it would go directly to my final destination spot in Orlando. I asked two employees and they both confirmed this and I tried to show the first on at baggage service center the pink tag and explained everything and she did not say that it was not like a regular checked bag and would need to be picked up at the jet way before my connecting flight. I was almost late to that flight with waiting at bag claim and asking assistance and running all the way back to the gate as well. I waiting 5 hours at the airport in Orlando after for my bag. It was just not a good start to my work trip this week.