The plane descends and I start to get nervous. It has nothing to do with fear of crashing. Sometimes I think that would be the preferable outcome. No, instead the fear is due to a game of Russian roulette my body plays on each landing. You see, occasionally I suffer from barotrauma headaches (related to, or also known as aerosinusitis). At least that’s the self-diagnosis.
As we lose altitude, I’ll feel a burning sensation just under the skin of my forehead, near the hairline. It’s always the left side. As though blood in my veins were boiling, the pain increases and spreads until it reaches behind my left eye. It takes only a few seconds for it to spread, and leaves me with 10 to sometimes 20 minutes of agony before we land. My body starts involuntarily shaking. I begin to worry that this time I’m not going to be left unscarred, this time my eardrum is going to rupture or pop.
The first time this occurred I was on a flight from Salt Lake City to Columbus, Ohio. It was within a month of September 11th, 2001. I woke up from a short nap with such intense pain that I honestly feared I might be dying. I thought this must be what a brain aneurysm felt like. The flight attendant took note of my anxious and pained condition, but offered nothing more than the knowledge that we would land soon and hope of a medical professional at the airport. I’m not sure if it was the heightened sensitivities of days following the terrorist strikes or if my own behavior was simply terrifying enough, but I ended up being taken off the plane on a stretcher. The paramedics in Columbus gave me water, some pills and a place to rest for an hour or two until I felt well enough to drive home.
After that first experience, I can recognize the warning signs and be a bit more prepared. A flight attendant will usually find time during the busy landing sequence to attend to me. With only one exception, they all appear to recognize what’s going on and why I’m making an odd request: two boiling-hot towels stuffed into the bottom of two cups. These both end up tightly pressed around my ears. If I didn’t already look insane because of the shaking, sweating and nervous stroking of my face, I definitely pass the crazy threshold when I clamp two cups to my head. I don’t care. If the other passengers had any idea how bad this hurt, they’d try any wacko remedy they came across too.
The cup trick was taught to me by a flight attendant and in my experience it has helped. The headaches are most likely caused by improper de-pressurization of the sinuses. My guess is that the hot moist air trapped in the cups helps open up sinus passages, allowing normalization. I don’t think I hold them tight enough to make any difference in air pressure. Who knows, could just be a trick to have me think about something other than my brain exploding.
This drama thankfully doesn’t happen on each flight. It doesn’t seem to happen on most flights. But in the last 5 or 6 years, I’ve experienced this at least 5 or 6 times. It’s often enough that each flight is a spin of the wheel. For example, to get from Hong Kong to Portland, I took three flights with layovers in Beijing and San Francisco. It was only on landing in San Francisco that I wanted to cry. The flight to Portland was shortly afterwards, and I had steaming cups ready as I was still sore from the earlier attack. I had also drank as much water as a could between the flights, hoping that would help. The Portland landing was fairly smooth and what pain I did have could have just been left over from the earlier flight. So why one of out three? Was it the longer flight? The little nap I took just before landing? Did my sinus conditions really change all that much between three consecutive flights?
Relating pain to others is tricky. If something hurts bad enough to warrant talking about, then there’s a temptation to exaggerate the experience to ward off those skeptic or unempathetic and garner attention worthy of the trauma. A google search for ”airplane headache landing” returns around 350,000 accounts, many of which mirror mine. If you’ve experienced this yourself, I’d really like to hear about it. Likewise, if you’re traveling soon and you have a stuffy nose or a history of sinus conditions, take a decongestant such as pseudoephedrine before your fly. And stay hydrated before and during the flight. Finally, if you ever come across someone in trauma during landing, you can suggest the cup trick. It can’t hurt (well, unless the towels are scalding and burn their ears, but then they’ll at least have something else to think about).

§Commentary
Stephen suffers from this too - and has gotten great relief from taking an anti-histamine tablet shortly before the descent starts. It doesn’t seem to completely prevent this happening, but gets the pain down to an “ouch”-y level, instead of the “oh wow, I need to tear my eyeballs out” alternative.
I’ve had it happen, but only once - eight hour flight with a raging sinus infection. Exactly what you described, and I thought I was having a stroke or something. For some reason, that infection took two months to clear up after that (I avoid antibiotics if at all feasible) and I’m convinced it got much, much worse because of flying. But >100 take-offs and landings later, it’s never reoccurred (neither have I had a serious sinus infection since then).