Being in the aviation industry and having been through Dangerous Goods training recently, I would add make sure to remove/disconnect/isolate batteries/power sources from dive torches and video lights especially as they are considered as fire hazards since they can get quite hot.
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UW photo gear in carry on - any no-no?
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I accidentally left a 2lb weight in my Ewa marine bag. That earned me a hand check at security and I had to open up the bag for a full screening. 😆. But no issues at all on my return trip. I carried on a legal overhead bin size roll aboard specifically for my UW gear and it worked out great.
I also kept a small tote bag in the roll aboard. My plan was if they made me gate check it for my short flight on the smaller commuter plane I would put the most delicate items (specifically my housing and batteries) in the tote to be able to carry that on.
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I always get stopped for camera gear. Here's my biggest tips:
1) Have covers over your batteries! I've started carrying some gaffers tape for them.
2) If they do ask you to check your carry on, explain there is camera gear and batteries in there. Usually they will find you a small enough space if you are following #3.
3) Always use a backpack for the primary amount of gear. I've never been asked to weight my backpack. Messenger bags are a good second alternative. Anything rolling or hard sided gets weighed first.
4) Carry a collapsable duffle bag. This will let you spread the weight if you have to.
5) Check whatever gear you can safely. This is usually the metal stuff.
6) Be Nice! Rules only have to be enforced when necessary and most staff really don't want to have to enforce them.
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Great tip about taking out the o-ring ... gotta remember that for next time!!
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I usually carry my UW housing, Ports, strobes, and batteries in a wheeled carry on. It' s usually 25 lbs. and 15lbs is the allowable max. Most time's no one checks the weight. But I have been stoped and checked twice, both times I opened the bag and showed them the housing and large dome port and stated that it was camera gear and fragile. They let me go, no charge.
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I always carry my UW gear with me. Never had a backpack weighed, although on a few occasions my carry on was weighed (only for international). I was able to step away and take out something then re-weigh.
Ultimately, you can try to the response "airlines don't insure photography equipment in checked bags...". Be nice, patient, and you should be fine.
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Airport Security took my Nauticam allen wrench set in Crete. We was also detained because their "bomb detection device" did not like the glycerin in my divers ear drops. They went kinda nuts when the machine kept triggering on my mask box for explosives. I now carry only vinegar and alcohol.

My wife and I were screened 3 times, including again at the gate. I use the Pelican air as a carry on.
Last, If you gave a Backscatter type vacuum port you can plug the gauge in the port and not worry about pressure.
K