Simply put, is this legal: Let's say I had an IRA with $100K and a non-IRA brokerage account with $100K . My aim, for tax purposes, is to generate losses in the non- IRA account but have off-setting positions in the IRA. I would be selling OTM futures option premium in the IRA and buying the same contract in the non-IRA. (Let's say the options have a probability of <10 percent of going ITM. ) Yes, I risk an accidental taxable gain offset -- except for the taxes paid -- if the Non-IRA profits and the IRA loses. Small risk, it seems. But if the inverse happens, I get a taxable-deductible loss in the non-IRA and a tax-deferred gain in the IRA, no? One could effectively move funds into an IRA as easily as into any other account and trade tax-deferred, right? And with futures and futures options, no need to worry about it being used for margin in an IRA, because that is permissible. What am I missing here? An obvious law, I should be aware of? If it is not legal, what's the cite or if anyone has a clip of the code.