Trigger valve most likely problem. You could also just replace the two orings on the trigger stem within the triger valve. They are very small (2mm). There are two or three other orings inside the gun that need to be replaced as well. The yellow vinyl orings used by dewalt do not last as long as the black rubber.
SOURCE: porter cable brad nailer only fires brad on second trigger pull
The dent in the wood is not caused by the air. It's caused by the set that drives the brad. Are you oiling it consistenly? Are the brads the right manufacturer for your porter cable brad nailer? From the information you give it appears that the brads are not advancing correctly or that the air pressure is not sufficient to dislodge the brad from the brad strip on the first strike - it takes an additional strike to break it free. The standard for adding oil is to add ten drops of air tool oil for every hour of operation. That seems like a lot, but the correct amount of oil is a sure way to prevent most air tool problems.
Testimonial: "Thanks for the info. I was not oiling it at that rate. Is there anything I can do to fix the issue now that I didn't prevent it?"
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