I’m researching a potential move to Puerto Rico under Puerto Rico Act 60 Chapter 2 (resident investor decree) and wanted feedback from people familiar with the tax side of active options and/or crypto trading.

    My understanding is that Chapter 2 is not limited strictly to passive long-term investing. Puerto Rico tax law broadly defines capital gains and specifically treats certain gains/losses from options activity as short-term capital gains or losses.

    My situation:

    • Planning to apply for a Chapter 2 decree before end of 2026
    • Move to PR around 1/1/2027 and become a bona fide resident under IRC §937
    • Spend the large majority of my time in Puerto Rico (~300 days/year)
    • Rent initially, then buy a primary residence in PR
    • PR driver’s license, voter registration, bank accounts, etc.
    • No meaningful center of life outside Puerto Rico after relocating

    Trading structure:

    • Personal brokerage account only (under my SSN)
    • Separate/new brokerage account funded with already-taxed mainland cash after relocation
    • No pre-move investments/gains realized after moving
    • No outside investors or customers
    • No LLC/corporation for trading
    • No §475(f) mark-to-market election

    Trading style:

    • Mostly defined-risk options strategies:
      • iron condors
      • debit spreads
      • collars
    • Usually held 1–2 weeks, occasionally longer

    My understanding is:

    • Under IRS Topic 429, a trader without a §475 election can still retain capital-gain treatment
    • IRC §1234 generally treats options gains/losses as capital gains
    • Under IRC §865, gains from sale of personal property are generally sourced to the taxpayer’s tax home
    • If I become a bona fide PR resident and generate gains after relocation, those gains may become Puerto Rico-source income
    • Under IRC §933, Puerto Rico-source income of bona fide residents is generally excluded from U.S. federal tax

    So the theory is NOT:
    “short-term gains magically become tax free”

    But rather:

    • short-term options gains still retain capital-gain character,
    • they become Puerto Rico-source after establishing residency,
    • and Chapter 2 potentially applies to qualifying post-move gains.

    I also understand U.S.-source dividends/interest may still be federally taxable, and I’m not trying to claim otherwise.

    I’m also not trying to force this into an export-services/business-income theory — the activity would simply be personal proprietary trading using my own capital.

    Main question:
    Has anyone here successfully structured active personal options trading this way under Chapter 2? And has anyone seen the IRS argue that short-term options trading without §475 somehow becomes ordinary income solely because the activity is frequent/business-like?

    Appreciate any insight from people who have dealt with this directly.

    IRC §933 + Act 60 Question: Short-Term Options Trading in PR Without §475(f). Do short-term options gains still retain capital-gain character?
    byu/PurveyancePrinciple intax



    Posted by PurveyancePrinciple

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