<p>@dstark – a hedging transaction is any one that effectively changes the risks of an investment – so, for example, the most simple would be when an investor who holds a stock buys a protective put. But other sort of options would also be hedges if they they essentially neutralize or change the effect of a move in the stock.</p>
<p>DocT had said that his taxable account doesn’t allow him to do spreads such as the condor you suggested - but that he might hang onto the puts in his taxable account but set up the spread in his retirement account.</p>
<p>That would be a hedge for the exact reason you suggested it: it ameliorates the risk of the losing puts. DocT loses on his puts when AAPL goes down, but he gets money back on the condor if it is set up right.</p>
<p>But IRS would not be happy. DocT was just thinking of salvaging a single bad investment, but think how easy it would be for a savvy investor to create paper losses in a taxable account and offset them all in a retirement account. Those of us who are over age 59 1/2 but under age 70 are in a very sweet spot with our retirement accounts. We have full access to the funds if and when we need them, but we are no required to ever take the funds. A Roth IRA is a double blessing – if we can manage to grow the funds exponentially, that’s a big, tax-free pay off down the line. </p>
<p>So IRS says that stuff has to be reported. </p>
<p>I have no clue how IRS enforces that rule, and being that it is a rule written by IRS, it’s a lot more complicated than that, with all sorts of ins and outs and ifs and buts. I found out about the rule when I was considering doing something along the lines of what DocT suggested, and realize that I was treading on dangerous ground. I didn’t go farther than that. </p>
<p>But I just wanted to raise the warning flag for DocT. </p>
<p>His rolling the puts in the same account is not a problem at all – it was the other idea that I was responding to. It doesn’t create an IRS problem when the options are rolled because all of the gains and losses in the taxable account will be reported to IRS by the brokerage – and rolling out an option is not a hedging move in any case. The only thing to worry about in the taxable accounts are the wash sale rules, where the transaction takes place after the first of the year. </p>
<p>So when I mentioned that I like to close out the losses by December, I also know to refrain from buying back the same stock at a lower cost during the first 30 days of the new year, to avoid the wash sale problem. </p>