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That's normal in my experience. Tires heat up on the road, pressure increases and it deflates to normal pressure upon startup. Give it a minute to situate itself.
The slight flare on the tube is only to keep the nut from slipping off, not a sealing surface. Some tubes actually don't have any flare at all on the end and seal just fine. The seal is accomplished when you tighten up the nut onto the wheel valve nipple (male threads) and the rubber seal inside...
So if it leaks at the compression nut, is it stripped and loose or does it tighten down? They strip VERY easily especially with an 1 1/8" wrench. If it isn't stripped, either the rubber seal inside is missing or worn out. I made new ones from 5/8" id heater hose.
You need to post a picture of what you're talking about. Are you referring to the tube that comes out of the axle hub that the wheel valve slides over?
Check and make sure that all of the wheel valves are seated properly on the tubes/fittings . Check for leaks. I had the exact thing happen and had to wire the wheel valve into position until I replaced the compression seal.
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