Hello, wondering if anyone can help with this question. The way the tax law is written is a little confusing so I haven't been able to figure out the answer on my own. Here is the situation: If I hold 50 shares of stock (short term <12 months) and go short 100 shares of the same stock in the same account, that puts me "short against the box." I am trying to find the tax implications of what happens if I stay short for a few weeks and then close out the short while keeping my long position. Does my holding period for the long shares become the date I close the short position? There seems to be a loophole condition where by if I close the short within 30 days of the end of the year and then do not make any other hedging strategies on the 50 shares of long stock for 60 days, there will be no tax consequences on the 50 long shares. Any help is appreciated.