Tax Loss HarvestingYear-end TLH realize losses
Sell loss positions before Dec 31 to offset gains; up to $3000 ordinary income offset
Source: schwab.com
Tax Loss HarvestingDirect indexing TLH
Hold individual stocks to harvest losses on losers within index
Source: schwab.com
Tax Loss HarvestingETF substitute swap
Sell SPY at loss; buy IVV/VOO immediately (not substantially identical)
Source: schwab.com
Tax Loss HarvestingSector ETF rotation TLH
Rotate between similar sector ETFs to avoid wash sale while maintaining exposure
Source: schwab.com
Tax Loss HarvestingCrypto TLH no wash sale rule
Sell BTC at loss; immediately repurchase - wash sale doesn't apply to crypto (yet)
Source: greentradertax.com
Tax Loss HarvestingMutual fund TLH year-end
Pre-distribution day sells avoid year-end cap gains distributions
Source: schwab.com
Tax Loss HarvestingBond TLH duration swap
Swap one bond for another with similar but not identical duration/credit
Source: schwab.com
Tax Loss HarvestingCarryforward losses
Carry forward unused capital losses to offset future gains
Source: irs.gov
Wash Sale30-day wash sale window avoidance
Don't repurchase substantially identical security 30 days before/after loss sale
Source: schwab.com
Wash SaleSpousal IRA wash sale trap
Wash sale applies across spousal accounts and IRAs
Source: schwab.com
Wash SaleSubstantially identical determination
Different ETFs tracking similar indices may not be substantially identical
Source: schwab.com
Wash SaleSection 1256 wash-sale exemption
1256 contracts (futures/index options) NOT subject to wash sale rules
Source: greentradertax.com
Wash SaleCrypto wash-sale exemption
Crypto not securities under current law; wash sale doesn't apply (legislation pending)
Source: greentradertax.com
1256 ContractsSection 1256 60/40 treatment
60% LTCG 40% STCG regardless of holding period - lower blended rate
Source: schwab.com
1256 ContractsMark-to-market year-end
Open positions deemed sold at FMV Dec 31 - tax on unrealized gains
Source: schwab.com
1256 ContractsSPX vs SPY tax preference
SPX (cash-settled index option) is 1256 - 60/40; SPY (ETF option) is regular STCG
Source: greentradertax.com
1256 ContractsNDX vs QQQ tax preference
NDX gets 1256 60/40; QQQ does not
Source: greentradertax.com
1256 ContractsRUT vs IWM tax preference
RUT gets 1256 60/40; IWM does not
Source: greentradertax.com
1256 ContractsVIX options 1256 treatment
VIX options qualify as 1256 broad-based index options
Source: greentradertax.com
1256 ContractsForeign currency forward 1256
Major currency forwards qualify for 60/40 treatment
Source: greentradertax.com
1256 ContractsLoss carryback 3 years
Section 1256 losses can be carried back 3 years to offset prior gains
Source: schwab.com
1256 ContractsBitcoin futures CME 1256
CME BTC/ETH futures qualify for 1256 60/40 - much better than spot
Source: greentradertax.com
1256 ContractsBITO ETF 1256 indirect
BITO ETF holds 1256 contracts internally; investor gets indirect 60/40 benefit
Source: greentradertax.com
Qualified DividendsHold for QDI period
Hold dividend stocks 60+ days for qualified dividend treatment
Source: irs.gov
Qualified DividendsAvoid margin substitute payments
Margin lending creates substitute payments taxed as ordinary
Source: schwab.com
Qualified DividendsREIT distributions ordinary tax
Most REIT distributions taxed at ordinary rates not qualified
Source: irs.gov
Qualified DividendsREIT 199A 20% deduction
REIT non-QDI dividends get 20% pass-through deduction up to TCJA limits
Source: irs.gov
Qualified DividendsForeign QDI treaty list
Specific list of treaty countries; non-treaty foreign dividends ordinary
Source: irs.gov
MLP K-1MLP partnership distributions
K-1 issued; ROC reduces basis; not eligible for QDI
Source: irs.gov
MLP K-1UBTI in IRA from MLP
Holding MLP in IRA can trigger UBTI tax above $1000
Source: irs.gov
Asset LocationBonds in tax-advantaged accounts
Hold high-yield bonds in IRA/401k; equities in taxable
Source: bogleheads.org
Asset LocationTax-efficient ETFs in taxable
Low-turnover ETFs in taxable; high-turnover funds in tax-advantaged
Source: bogleheads.org
Asset LocationActive stocks in tax-advantaged
Frequent trading in IRA/401k avoids realization events
Source: bogleheads.org
Asset LocationRoth optimization growth
Hold highest-growth assets in Roth for tax-free compounding
Source: bogleheads.org
Asset LocationForeign tax credit foreign in taxable
Foreign equities in taxable to claim foreign tax credit
Source: irs.gov
Roth ConversionRoth conversion in low-income year
Convert IRA to Roth in low-income years (job loss/early retirement)
Source: bogleheads.org
Roth ConversionRoth ladder for early retirement
Convert traditional in chunks; access converted amounts after 5y waiting
Source: bogleheads.org
Roth ConversionMega backdoor Roth (after-tax)
Use after-tax 401k contributions and in-service rollovers to fund Roth >limits
Source: bogleheads.org
Roth ConversionBackdoor Roth (non-deductible IRA)
Contribute non-deductible IRA then immediately convert; pro-rata rule applies
Source: bogleheads.org
ISO/NSOISO exercise timing
Exercise ISOs to qualify for LTCG (1+2 year rule); watch AMT
Source: irs.gov
ISO/NSOISO disqualifying disposition
Sell ISO shares <2y/1y = ordinary income on bargain element
Source: irs.gov
ISO/NSONSO exercise hold strategy
NSO bargain at exercise = ordinary income; future gains LTCG if held 1y
Source: irs.gov
ISO/NSOSection 83(b) early exercise election
Pre-vest exercise + 83(b) shifts to LTCG starting at grant
Source: irs.gov
ISO/NSOAMT minimization on ISO
Stagger ISO exercises across years to manage AMT
Source: irs.gov
RSURSU vest tax planning
RSU value at vest = ordinary income; sell-to-cover tax
Source: irs.gov
RSURSU sell-immediate vs hold
Selling at vest avoids concentration; holding adds LTCG potential + risk
Source: irs.gov
RSURSU + ISO portfolio plan
Coordinate ISO exercise + RSU vest to balance ordinary vs LTCG
Source: irs.gov
CharityDonor Advised Fund (DAF)
Bunch deductions in one year via DAF; distribute to charities over time
Source: irs.gov
CharityAppreciated stock donation
Donate appreciated stock to charity; deduct FMV avoid cap gains
Source: irs.gov
CharityCharitable Remainder Trust (CRT)
CRT for highly appreciated assets; income stream + remainder to charity
Source: irs.gov
CharityQualified Charitable Distribution (QCD)
IRA distribution to charity (age 70.5+) reduces RMD without income recognition
Source: irs.gov
CharityStock-fund crossover
Donate appreciated stock; rebuy same stock with cash for stepped-up basis
Source: irs.gov
QSBSSection 1202 QSBS exclusion
Hold QSBS 5+ years; up to $10M or 10x basis tax-free gain
Source: irs.gov
QSBSQSBS state coordination
Some states (CA NJ etc) don't conform to QSBS; plan accordingly
Source: irs.gov
QSBSQSBS rollover Section 1045
Roll QSBS gains into another QSBS within 60 days; defers tax
Source: irs.gov
Opportunity ZoneQOF investment cap gain defer
Invest cap gains into QOZ Fund; defer until 2026 + step-up
Source: irs.gov
Opportunity ZoneQOZ 10-year hold elimination
Hold QOF 10 years to eliminate gain on the QOF investment itself
Source: irs.gov
1031 ExchangeLike-kind real estate exchange
Defer cap gains by trading investment real estate within 180 days
Source: irs.gov
1031 ExchangeReverse 1031 exchange
Buy replacement property first; sell relinquished within 180 days
Source: irs.gov
Step-Up BasisEstate step-up basis
Hold appreciated assets until death; heirs get stepped-up basis
Source: irs.gov
Step-Up BasisSpousal joint tenancy step-up
Joint tenancy with spouse provides ½ basis step-up at death
Source: irs.gov
Step-Up BasisCommunity property full step-up
Community property states get 100% step-up at death of one spouse
Source: irs.gov
EstateAnnual gift tax exclusion
Gift up to annual exclusion ($19k 2026) per recipient tax-free
Source: irs.gov
EstateLifetime gift tax exemption
Use lifetime exemption to gift appreciated assets at low values
Source: irs.gov
EstateGrantor Retained Annuity Trust (GRAT)
Zeroed-out GRAT transfers appreciation tax-free if grantor survives
Source: irs.gov
EstateFamily Limited Partnership (FLP)
Discount valuations on FLP interests for gift/estate purposes
Source: irs.gov
EstateSpousal Lifetime Access Trust (SLAT)
Use lifetime exemption while spouse retains access to assets
Source: irs.gov
Trader StatusTrader Tax Status (TTS)
IRS recognition allows business expense deductions for active traders
Source: greentradertax.com
Trader StatusSection 475 mark-to-market election
475 election: full ordinary income/loss; no wash sale; no $3k cap loss limit
Source: greentradertax.com
Trader StatusSchedule C trader expenses
Deduct home office equipment data fees etc. on Schedule C
Source: greentradertax.com
Trader StatusTrader entity LLC structure
Pass-through LLC for liability + self-employment retirement plans
Source: greentradertax.com
Trader StatusSolo 401k for trader entity
Use trader entity LLC to fund solo 401k for retirement
Source: greentradertax.com
Cap Gains RateLTCG rate management
Realize LTCG to fill 0% bracket (single <$48k MAGI 2026)
Source: irs.gov
Cap Gains RateTax-gain harvesting
Realize gains in low bracket to step up basis tax-free
Source: irs.gov
Cap Gains RateNet Investment Income Tax (NIIT)
Additional 3.8% NIIT on investment income above MAGI thresholds
Source: irs.gov
Cap Gains RateMulti-year cap gain spreading
Spread large gain across years via installment sale
Source: irs.gov
Cap Gains RateCollectibles 28% special rate
Collectibles (gold coins art) taxed at max 28% LTCG
Source: irs.gov
Cap Gains RateSection 1250 25% recapture
Real estate depreciation recapture taxed at 25% max
Source: irs.gov
Section 199AQBI 20% deduction pass-through
20% deduction on qualified business income from pass-through
Source: irs.gov
Section 199AREIT 199A dividend deduction
REIT dividends get 20% deduction without W-2 limitation
Source: irs.gov
Section 199ASSTB threshold awareness
Specified Service Trade Business loses 199A above income thresholds
Source: irs.gov
ForeignForeign Tax Credit
Claim FTC for foreign withholding on dividends/interest
Source: irs.gov
ForeignFBAR/FATCA filing
Report foreign accounts >$10k (FBAR) or $50k (FATCA)
Source: irs.gov
ForeignPFIC avoidance
Avoid PFIC (foreign mutual funds) - punitive tax treatment
Source: irs.gov
ForeignFEIE expat exclusion
Foreign Earned Income Exclusion for US expat workers ($120k+ 2026)
Source: irs.gov
CryptoCrypto specific identification
Use specific lot ID for crypto sales (not FIFO) to optimize gains
Source: greentradertax.com
CryptoCrypto staking ordinary income
Staking rewards = ordinary income at receipt FMV
Source: greentradertax.com
CryptoCrypto-to-crypto swap taxable
Crypto-to-crypto trades are taxable events; not like-kind
Source: greentradertax.com
CryptoDeFi yield farming taxable
DeFi rewards = ordinary income; LP token swaps = taxable
Source: greentradertax.com
CryptoForm 1099-DA reporting (2025+)
New broker reporting form for digital assets starting 2025
Source: greentradertax.com
Constructive SaleSection 1259 constructive sale
Don't accidentally trigger constructive sale via offsetting positions
Source: irs.gov
Constructive SaleShort against the box rule
Modern rules: shorting same stock you own = constructive sale
Source: irs.gov
Constructive SaleMarried put exception
Buying protective put while holding stock generally not constructive sale
Source: irs.gov
Indian TaxSTCG India 15% (now 20%)
Holding period <12m for Indian equity = STCG; rate increased post-2024
Source: incometaxindia.gov.in
Indian TaxLTCG India 10% (now 12.5%) over 1L
Equity LTCG over Rs 1.25L taxed at 12.5%
Source: incometaxindia.gov.in
Indian TaxF&O speculative income vs business
F&O income = business; can offset against other business income
Source: incometaxindia.gov.in
Indian TaxIndian STT on intraday
STT 0.025% sell side intraday equity; factor into edge
Source: incometaxindia.gov.in
Indian TaxGST on brokerage 18%
18% GST on brokerage and exchange fees increases effective cost
Source: incometaxindia.gov.in
RecordkeepingTrade log for tax compliance
Maintain detailed trade logs for audit defense
Source: irs.gov
RecordkeepingCost basis methods (FIFO LIFO HIFO SpecID)
Use SpecID where possible to optimize realized gains/losses
Source: irs.gov
An encyclopedia of publicly documented strategies for education. YCAI does not recommend, endorse, or trade any of these. Not investment advice.