Been looking into this pressure issue since it's a known technical flaw in the newer builds. Honestly, Sony WH-1000XM5 Wireless Noise Cancelling Headphones are a bit of a letdown for long-haul flights. The 'Auto NC Optimizer' is frustrating because you can't manually trigger the atmospheric pressure sensor anymore. It just does what it wants, which usually means the pressure suck gets worse when the cabin altitude changes. If you're worried about reliability, here's how they stack up:

• Sony WH-1000XM4 Wireless Noise Cancelling Headphones: Safer bet. You still get the manual optimizer button to fix that ear-suck feeling. Folding hinge is better for packing too, tho the tech is getting old.
• Bose QuietComfort Ultra Wireless Noise Cancelling Headphones: If Sony is hurting your ears, these are the alternative. The tech handles cabin pressure more smoothly without that vise-grip feeling. Unfortunately, the XM5 is just not as good as expected for actual travelers.

Listen, if the pressure thing is what's killing you, dont overthink it. Just grab the Sony WH-1000XM4 Wireless Noise Cancelling Headphones while you still can. I have been using them for ages and they are way better for travel than the new ones imo.

• Manual Atmospheric Pressure Optimizer: This is the big one. You can actually trigger it in the app once you are at cruising altitude. The XM5 tries to do it automatically and it usually fails to adjust properly.
• Folding design: They actually fold up small which is way better for a packed carry-on compared to the new case.
• Price: You can find them for like $280-300 now, so you save a ton of cash for your actual trip. The ear pads are super soft too, never had an issue with them pinching my head even after 8 hours. Honestly, sticking with the older tech here is the move if you want to avoid that cabin pressure suck feeling.

If the pressure suck is the main issue, sometimes going for the flagship isnt the best move. The high-end models have such aggressive ANC that it actually causes that discomfort for some people. Maybe try these tips:

• Look at the Sony WH-CH720N Wireless Noise Cancelling Headphones because they are way lighter which helps with the vise-grip feeling during long hauls.
• Use the Ambient Sound Control slider in the app to dial back the ANC intensity if the full Noise Canceling mode feels too heavy on your eardrums.
• Check if your ear pads are worn out. Replacing them with thicker ones can sometimes fix the seal issue without needing a whole new headset. The CH720N might not feel as fancy as the XM series, but for a 14-hour flight, the lower weight and less intense pressure might actually be better for your head. Plus they are way under your budget so it is a pretty low-risk experiment.

I think the newer model might help with that pressure. Honestly, I'm super satisfied with how mine feel on long hauls.

• lighter frame
• better seals Not sure about the auto-anc tho...

Gonna try this over the weekend. Will report back if it works!