Before the current I-94 expires.
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Make sure you apply before her current status expires. Generally, you are supposed to apply as soon as you know you will need an extension. Submit all supporting documents required. Good luck!
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Apply before I-94 terms and present compelling documentation of her intended stay in the U.S.
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It might, the reason needs to be compelling. Not sure if her getting chiropractic treatments is compelling, they could say go to your home country to get those unless her chiropractor says she can't travel. You might want to wait until you are closer to the January date since she is in lawful status while the extension request is pending. If her extension is denied post January 2014, however, she will be expected to leave the country immediately.
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