Enter USA on VWP after B2 overstay?

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As I understand it you timely filed the I-539, included the filing fee and have no particular reason to think the application wasn't accepted, but left before getting a response. If this is what you are asserting then you have no particular reason to think you did anything wrong and can only be wondering if the US sees this the same way.

If this is the case then the easiest way to find that out might be to apply for an ESTA for the new passport. Answer all the questions accurately, including the one asking about your other passport. If that application succeeds it is a pretty good indication that they are not unhappy with you, if it fails you'll know for sure that you need to pursue a visa.

I think the ESTA application is about the simplest and most authoritative way to get an answer to your question. They will know what happened with the I-539.

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