The problem is that you get into wash sale rules [0]. Most people are not aware of this, but wash sales can be impacted by securities owned in retirement accoun

The problem is that you get into wash sale rules [0]. Most people are not aware of this, but wash sales can be impacted by securities owned in retirement accounts [1]. Worse, the aspect of options and "substantially similar" securities starts to get arcane fast. Meaning, you really want a tax lawyer involved on a complex transaction like that. Otherwise, you may find that you've apparently made a ton of money, and then a few years later the IRS knocks on your door and asks for all your profits in a nice check paid to US Treasury. (I'm not saying you can or cannot do this, only that the tax law gets complicated fast.) [0] - (page 56) - https://www.irs.gov/pub/irs-pdf/p550.pdf https://www.irs.gov/pub/irs-pdf/p550.pdf [1] - https://www.irs.gov/pub/irs-drop/rr-08-05.pdf https://www.irs.gov/pub/irs-drop/rr-08-05.pdf ======= EDIT - meant to add that "sale or other disposition" includes the expiration of an option. So you don't actually have to sell to incur the wash sale situation.