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Looks like there was a bend in the presta valve. Note you don't need to unscrew the valve all the way out when you inflate your tire, needs only 1 full turn or so, this makes it less prone to bending and breakage when installing/removing the pumphead. You also don't need to reef on the valve when tightening it because presta valves are held closed by air pressure and are not mechanical like schraeder valves are. So just screw the presta valve barely finger tight and all will be good.
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