If I have some big losses on covered calls is there any downside to rolling those now (or this fall) rather than waiting until closer to expiration in Jan 2025? My logic would be to lock in loss for 2024 tax purposes to offset realized 24 STCG and also that I'd like to keep rolling these indefinitely so no reason to wait.

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You have a short call loss, not a covered call loss. Is your equity a long term holding? I would never have a short call out more than 30 days, the delta risk is high, and the theta gain is low. Roll any short call into a September expiration, take the loss, and hold off on tax loss harvesting until closer to the end of the year.

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I do my tax loss harvesting in November when I know where I stand.

Oh, and good luck.

It depends how much you are in the money…..or not and your perspective on how it will perform in the future. No straight answer

I'm asking from a tax perspective as it almost seems too good to be true to take a large STCL without any real economic loss.

I plan to keep rolling longer term covered calls and continue to hold the stock long term because I think it will continue to grow steadily (and I have significant, to me, unrealized gains in taxable brokerage).

Strike price 67.5 exp early 2025, current price 71. I can push back a month to realize the loss and make roughly $50/each at same strike or can push back five months and increase strike to 70 for about even. Leaning towards the latter but may split between the two.

How did you lose on covered calls?

This is in a taxable amount so allowing it to be exercised would trigger a pretty significant gain. I like the stock long term so rather than a wheel strategy I plan to just keep rolling.

Realized loss not economic loss.

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