In 2002 I was charged with obstruction of justice. It was a summary offence and I went through the adult diversion program and then my charge was withdrawn. Fast forward to 2009, my then boyfriend and I drove from Canada to Las Vegas for a road trip. At the border I was asked if I was ever charged and I truthfully answered yes. I got pulled into secondary screening, had to fill out forms and also explain to them about my charge and what happened. They told me next time I travel to the US, that I need to bring my court papers to show them. Has anyone else experienced this and did you successfully entered into the US again after you showed your court papers? Am I now flagged? What are the chances of me being denied? I want to take my daughter to Florida Disneyworld but this is causing me to worry.
Next time, you need to bring your court papers to show them
They told you that. I gather you did not misunderstand, since you repeated it here.
"Am I now flagged"? Yes, you might have made a common error of assumption: that immigration is a bunch of stupid border guards who have never heard of computers.
Yes, every US border guard you encounter may instantly call up your history with all US border guards. Expect the guard to see a comment like
2009/8/5 decl past charge sec screen discl 2002 settl obstruct justice.
2009/8/5 told to bring court papers next visit
I expect this to be no big deal. Since, if it was a big deal, they would've refused you 11 years ago, when the crime was fresher, at the highway crossing where it's super easy to turn people away -- Canada has to let you back in, and no expensive airline itineraries have been disrupted. (not true if you fly into JFK and are refused there; it gets messy fast.)
But, the formality should not be neglected. You do not want immigration to think you consider immigration law unimportant. They are trusting you to abide by the terms of your visa or waiver.