Frequently Asked Questions
How does tax-loss harvesting work?
You sell a losing position to realize a capital loss, which offsets capital gains and up to $3,000/year of ordinary income. Excess losses carry forward indefinitely. The proceeds are reinvested in a similar (but not "substantially identical") security.
What is the wash-sale rule?
You cannot claim a loss if you buy the same or "substantially identical" security within 30 days before or after the sale. Buying back into a similar but not identical fund (e.g., swapping VTI for ITOT) is a common workaround.
What is the value of harvesting losses?
For a high-bracket investor (37% federal + state), every $10,000 of harvested loss can save $3,500-$5,000 in current taxes. Studies estimate annual after-tax alpha of 0.5-1.5% in volatile markets.
Are there pitfalls?
Yes: you reset cost basis lower, increasing future taxable gains. The strategy provides a deferral, not permanent savings, unless you donate appreciated shares or hold until death (step-up in basis). It also requires meticulous record-keeping.
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