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谢谢8老师

Here was his plan:
Sophomore year – study for 12 months (allowed by the college).
Junior year – intern for the first 3 months, study for 6 months, then intern again for the last 3 months.
-That will not work. He only can work at full-time job during the school vacation/break such as summer time. 

Based on your explanation, due to the duration of his study in Junior year, he will not be able to maintain his F-1 status. As a result of which, he will not obtain an OPT for his second internship, correct?
-Right. Talk to the school International Student Office and they know this thing well.