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wild_b_cat t1_j2a5lo8 wrote

The only downside is if you're in a low income year. If you are, then this year you want to harvest gains and not losses, particularly if you can do so in the 0% long-term cap gains bracket.

Otherwise, TLH is generally beneficial if you're in your working years, since it's moving some income from this year to a future year when your tax rate will probably be lower.

That being said, if you need to sell investments to fund a Roth IRA, that typically makes sense whether those investments are at a gain or a loss.

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RealAustinNative OP t1_j2amv6h wrote

That’s a good point! I’m solidly mid career and not sure I will have the extra money for the IRA in 2023 if I don’t get it from the brokerage, so I guess my only concern here is the wash sale.

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vynm2 t1_j2canq3 wrote

Don't repurchase the same or substantially identical security in the Roth. If you do, you will trigger the wash sale and not be able to realize the losses.

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