We study investors’ responses to increasing tax reporting awareness and scrutiny in the crypto markets. Using novel data on retail investors’ trading, we ocument significant taxation effects on investors’ behavior and preferences for crypto-exchanges. Investors engage in tax-loss harvesting through wash trading and trading new products such as non-fungible tokens, consistent with the motive to minimize taxable events, improve tax reporting quality, and balance portfolio losses. U.S.-based traders engage in more tax-loss harvesting at the end of the year than their international peers. We further examine billions of trades on the trading books of large crypto exchanges and discover widespread tax-loss harvesting trades on U.S.-based crypto exchanges, amounting to billions of dollars in tax revenue losses for the government. Finally, we discuss ongoing anti-tax-loss harvesting proposals in anticipation of traders’ likely reactions.