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Visitors Visa Extension

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10 yrs Visa
I have this question. My boyfriend has been going back and forth to my country back 4 yrs. He came to united states with a 10 yrs visa. He has been working and brought property ( apartment) in the united states. He was a business man in my country.
He has received a letter from immigration stating that he has to leave the US on December but he had to attend a business form. Therefore, His lawyer and him send a letter to the immigration requesting an extention for his stay and send all the necessary documentation.
On June, he received a letter from the immigration stating that this time he has to leave on june 16th. Which he did leave.
Now he stayed in my country for couple of weeks and now he is in amsterdam and will be entering the united states from there. will they give him a problem when he is entering the united states because he extended his visa on december? Has anyone experience anything similar to situation like this
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