I purchase ACN stock monthly which means I can’t claim a capital loss (due to wash sale rules). Even still, is it correct that it’s better to sell a share at a loss vs a share with gains? (I.e., while I wouldn’t get to claim a loss, I also don’t need to claim a gain)

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Wut?

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Makes sense. Yes, I could have been more clear. I need to sell to diversify so seems logical to sell the shares with lowest tax liability.

Even if you can't claim the loss now, a disallowed wash would result in upward adjustment of your remaining shares basis, so it will eventually offset the gains when you sell those.

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I assume you are selling and buying something else to diversify. That is probably a good idea. I assume you would rather sell at a gain since that means you made money. Selling at a loss is better for lower taxes but also lower for after tax returns. Really depends on what you are trying to do.

If you have wash losses, it really makes no difference, but yes if you want to sell some shares you have, selling those with the lowest basis would be better for tax now. It will even out in the long run, but you would be deferring tax.

Nobody hod question why you are doing this monthly - in addition to maxing SPP, I assume

Yeah, I’m wondering why you are buying ACN stock monthly at all? You can do the ESPP program to invest in ACN. Since you know about wash sales, though, I assume you’re a knowledgeable investor, so I’m curious what your reason is.

Through the MD VEIP program share are purchased monthly.

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