I've read horror stories about someone selling stock A for a loss in a traditional brokerage and rebuying the stock in an IRA. Their basis in their IRA does not ever adjust and they cannot ever realize the loss. However, imagine the following hypothetical scenario:
Someone buys 100 shares of Stock A in their traditional brokerage for $50 each, sells a month later for $25 each ($2500 loss). Then, one day later, they rebuy one or more shares Stock A for 26 dollars in their traditional brokerage. Then, the day after that, they buy Stock A in their IRA.
When they sell Stock A again in their traditional brokerage after 30 days, are they allowed to take the deferred loss, assuming they've sold in their IRA too? In other words, do you get to choose where you apply the deferred loss?