"What if we long a deep in the money put/LEAPS put in IRA and long a deep in the money call/ LEAPS Call of the same underlying in RothIRA and actually we are speculating that the underlying to be the upside so when we close the position one day, IRA put option will lost money while your RothIRA call increase in value. If we can continue to do this with success we'll be able to withdraw from RothIRA tax free when we are 65 (damn IRS). Other than the commission this sound good to me cause I think I already pay too much tax in my life. The 2 bad case scenario will be A.The stock doesn't move at all you lost time value in both contract. B. Your speculation is wrong and stock drop significantly and your IRA earned money and your RothIRA lost (which is ok, we still have the money just try next one)" But there will be 2 good case too, if the stock drop significantly to the call strike (or rise significanly to the put strike) the time value will be possibly more than the TV combine when the trade is established (the position is worth more $ when they are established), if this happen on the upside. other than moving the money from IRA to ROTH we earn some extra $ How will IRS think about this? Any thought?