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Personal Investments • Tax-loss harvesting into 529 as contribution strategy?

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I was curious to hear people’s thoughts on a 529 contribution strategy to decrease the overall tax bill:

I plan to regularly purchase (VTI and BND) in a taxable account instead of my 529 but will “tax loss harvest” by selling securities at a loss in my taxable account and purchase those substantially different but correlated securities in the 529 instead.

Over a period long period (say 15 years), it seems unlikely that my taxable account will have gains on all tax lots of the securities at all times, yielding opportunities for tax loss harvesting. Because of buying those securities in the 529, the taxes are eliminated instead of deferred as in normal tax loss harvesting.

It seems this strategy might not work if there are not enough losses to take to meet my 529 saving goals.

Does this strategy make sense?

Statistics: Posted by bn88 — Tue Dec 10, 2024 8:51 am — Replies 5 — Views 116



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