A crafty Maryland resident managed to elude strict Transportation Security Administration checkpoints at Kennedy Airport and boarded a plane that was ready to take off — a massive security breach that he also pulled once before in Denver.

The Feb. 24 arrest of Ronald Wong, 30, came just six days after he fooled the TSA in San Francisco and was able to hop aboard a commercial flight to Denver without a ticket, sources said.

His wild antics are now the subject of an ongoing FBI-Joint Terrorism Task Force probe that could lead to new federal charges against him as early as today, sources said.

“This guy has exposed serious flaws in passenger security in at least two cities,” one official said.

“The TSA is aware and fully cooperating with the ongoing law-enforcement investigation,” said Ann Davis, a spokesman for the TSA.

Wong, of Chevy Chase, has a history of psychiatric problems, insisted his father, Peter, a certified public accountant.

The younger Wong was caught aboard Delta flight 127 on Feb. 24 using another passenger’s stolen boarding pass.