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Should I maintain my J1 status while my F1 is pending?

Short answer: Yes F-1 status can only be given up to 30 days before the program starts, and therefore you can only apply for Change of Status to F-1 if you were in status 30 days before the program start date. Furthermore, applications for Change of Status can take several months these days. If you miss the start of your program because Change of Status takes so long, your school will move your start date back. USCISs current interpretation is that when this start date postponement happens, you are required to have been in status 30 days before the new (postponed) start date, or your Change of Status will be denied. (I know, it doesnt make much sense, because it means you could be denied Change of Status just because it takes so long, where it otherwise could be approved if it took shorter time to adjudicate.) This means that, effectively, you have to remain in status for most of the Change of Status for it to work. You remain in J-1 status for 30 days (the grace period) after your J-1 program is completed. But since you said your J-1 finished in April, I believe that the grace period was already over in May, and you already havent had status for more than 30 days, and thus your Change of Status to F-1 will eventually be denied. One thing you could have done was applied for a separate bridge Change of Status to B-2 status right before your J-1 status ended (yes, you would have to pay another I-539 fee for that). The bridge B-2 status, when approved, will in turn provide a status during your Change of Status to F-1, thus allowing that to be approved. (This is analogous to the bridge B-2 Extension of Status mentioned in the linked page.) However, if you didnt apply for this bridge Change of Status before your J-1 status ended, it is too late now. Your only option may be to leave the US and get an F-1 visa.