One time I was using my Top Sider oil extractor to do an oil change on my 2016 Jeep. Same thing happened, started sucking air when I thought there was a little more oil in the pan. I twisted the nylon tube a little and it got stuck......which freaked me out a lot! I could not pull it back it was hung on something in the pan. Fortunately I removed the drain plug and was able to see it in the pan, I had my wife push it a little more, it kinked I grabbed it with a o-ring pick pulled it out of the drain plug hole, cut it off at the dip stick tube and pulled the whole tube out. IDK if I had let the nylon tubing go so long it got "fuzzy" from being in and out of places so many times on the end or what but that's the first and only time that ever happened. I routinely check my tubing and change it any time I see a bur or nick in in.