What is the funniest thing you've seen as a Jumpmaster?

I was jumpmastering a Casa212 at St Mere-Eglise for a USASOC fun jump. There was a female engineer captain that looked scared before we even got on the plane. I asked if she was okay and she admitted she was a little nervous. I reassured her and put her in the middle of the stick (she initially was the #1 jumper.)
Once we got in the air and I have the command "GO!" Every thing was going smoothly until I saw her coming with eyes closed, almost running. She sort of jumped, hit her head on the ceiling on the plane, bounced on her 4th point of contact, and fell out of the plane.
The next jumper, a friend of mine from 3rd SFG, was laughing to the point of tears.
When I got back to the ground I found her and made sure she was okay. Then I explained what she did wrong, how it could be bad for her on a lot of different levels, and told her to stick to jumping with her engineer unit.
This was back in 1999 or 2000. The next time I saw her she was a master blaster. I never wrapped my star.

I’m in the left door jump mastering over I want to say Salerno drop zone at Bragg, it’s been several years. As I’m squared up on the door and look out for my one minute reference point, I see a giant teardrop shape pond. I quickly get back inside the aircraft, I told the number one and the number two jumpers (Battalion commander and Sergeant Major) We’re over the wrong drop zone. No sooner do I get the words out of my mouth, the aircraft veers sharply to the right. I’m riding a wheelie in the left door, I looked over my shoulder and the captain jump mastering in the right door his face down towards the ground. I’m praying “ please God don’t let him fall out!” It was wild!!!

SSG Jeff Binkiewicz
I wasn't a Jump Master or even Parachutist qualified, but I have done some civilian sky diving, a tandem jump. My instructor fell asleep in the plane prior to the jump and I did find that a bit funny.

I watched a jumper turn a Casa jump into a UH-60.

I was an Air Force Combat Controller, who as going to be doing a HALO 20K night jump with my team. Knowing we had a new member jumping with us for the first time, gags were aplenty. just as we were about to go green, turbulence landed all of us on our butts as we watched the green light come on. Like fallen ice skaters making it back up and RUNNING for the RAMP~~we MUST'VE looked like a chinese fire drill exiting, because that's how it felt. I found myself laughing, trying to right myself and locate everyone else. Syncing up, everyone safe, there were smiles all around.

When jumping Hueys instead of pushing up and out we would momentarily stand on the skids then step off. I had an EN Captain try this once, he slipped and fell straight down with the skid becoming wedged between he his back and pack tray; he was a “Hung Jumper.” Having never been trained for this situation as a SSG 11-Bravo the solution became obvious. It was my third kick to pack that flipped him forward and rotated him free from the skid!

We were jumping a packed C141 and we stood up, hooked up when the red light came on, it slowed to 125 mph and the doors opened. The green light came on and we all started shuffling to the door to exit and instantly be ejected at 125 mph. Suddenly the whole line came to a quick halt and the green light turned red again. Never saw that after dozens of jumps.

They started hauling in the static lines of the few that cleared and jumped while we were over the drop zone. As one static line came in from outside the aircraft, I saw two hands attached to it. They clutched the inside of the door and a body attached was dragged back in. That guys static line was misrouted so his chute didn’t open and he must have spun outside the back of the plane as a few jumped past him. The pilot could tell their was drag and canceled the jump. That guy was in shock and kept saying he was spun crazy. After that, we all laughed but also double checked our static lines as should always be done on every jump for the guy in front of you.

I want the JM but watching my buddy slip down the ramp on a free fall jump and flip for a few thousand feet was funny once his chute opened. Best jump was when the osprey was going a little too fast and I felt my body slow down after exit!

I was sitting on the tail of the AC130 during a black out door jump in Ranger bn. Blackout means true blackout, no lights. We were jumping into a civilian airfield and i was counting bodies back on after exfil and completion of airfield seizure training. Anyway, I had nods on but I was lashed to the floor. AF hands the door to the JM, door checks occur and then standby; we run on a 6 min standup drill. First guy goes out the right door and the step breaks off the bird, I can't tell anyone cause I'm lashed down. I watch in horror as each guy goes to step where the step should be only to meet the crease of the door and violently spin out. The AF TAC P said the step landed 10 feet from him and embedded itself 3 feet in the ground

My Combat Control Team was running a joint jump with the Army, in Kentucky, in July! I was 22 and just an E-3 but already a Master Jumper with over 70 jumps. As JM I was responsible for a FULL C-130. As usual, the troops were all suited up on the ground, waiting to load. That, the heat on the tarmac and then in the plane, I knew that they WANTED TO GET OUT! CCT doesn't suit up until 15-20 minutes out and the flight to the drop zone was almost an hour, but I still felt bad for my planeload of guys, but even more for the loadmasters who had to clean up after! Door opens with a gust of fresh air and you could almost feel the relief throughout, but the smell, yikes. I don't think I've EVER had a faster group watching these guys leave the door, I got nods of thanks as they went out, they looked beat BEFORE the mission on the ground even got started. The training mission went great and I was even thanked by some of those guys for putting them right on target.