Tax Compliance & Planning (TCP) Cheat Sheet

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Our Tax Compliance and Planning (TCP) CPA Exam cheat sheet is optimized to simplify the complexities of advanced tax compliance and personal financial planning for test day success. This guide focuses on exactly what you need to pass, delivering clear explanations of heavily-tested topics in entity tax compliance, individual tax planning, and property transactions. Key concepts, like the wash sale rule, and critical calculations such as the kiddie tax are broken down, providing the essential knowledge you need to pass the TCP exam with confidence.

Studying for other sections? Check out our cheat sheets for FAR, AUD, REG, BAR, and ISC.

Individual Tax & Financial Planning

Basic Strategies & Income Types

Tax Strategies

  • Defer Taxable Income: Postpone recognition to a later tax year (leverages the time value of money).
  • Accelerate Tax Deductions: Take deductions currently to immediately reduce liability.

Net Investment Income Tax (NIIT)

High-income individuals are subject to a 3.8% Net Investment Income Tax on the lesser of:

  • Net Investment Income (NII): Interest, dividends, royalties, capital gains, net rental income, and non-material participation passive business income; OR
  • The excess of Modified Adjusted Gross Income (MAGI) over statutory thresholds:
    • $250,000 for Married Filing Jointly (or Qualifying Surviving Spouse)
    • $200,000 for Single or Head of Household
    • $125,000 for Married Filing Separately

International Taxation for Individuals: Exclusions & Residency

Foreign Earned Income Exclusion (FEIE): Qualifying U.S. citizens working abroad can elect to exclude foreign-earned income up to the Statutory Annual Indexed Limitation by satisfying either:

  1. Bona Fide Residence Test: Resident of a foreign country for an uninterrupted period covering an entire calendar tax year.
  2. Physical Presence Test: Physically present in a foreign country for at least 330 full days during any 12-consecutive-month period.

Substantial Presence Test (Inbound Nonresident Taxation): Nonresident aliens are taxed on worldwide income as U.S. tax residents if they meet the Substantial Presence Test:

$$ \text{Weighted Days} = (1.0 \times \text{CY Days}) + \left(\frac{1}{3} \times \text{PY1 Days}\right) + \left(\frac{1}{6} \times \text{PY2 Days}\right) \ge 183 \text{ days} $$

Requirement: Taxpayer must also be physically present in the U.S. for at least 31 days during the current year.

Income Categories

Category Examples
Active Salaries, wages, and income/loss from a business with material participation.
Passive Income/loss from business activities without material participation, rental real estate, and limited partnerships.
Portfolio Interest, dividends, royalties, and capital gains from investments.

Comprehensive Individual Loss Limitations

Losses from flow-through entities are applied sequentially against these four limitations. All four limitations (Tax Basis, At-Risk, Passive Activity, and Excess Business Loss) are calculated and applied at the individual taxpayer (partner or shareholder) level, rather than at the entity level.

graph TD Start["Flow-Through Entity Loss"] --> B{"1. Tax Basis Limitation"} B -->|Excess| SuspBasis["Suspended until basis is restored (Permanently lost upon total disposal)"] B -->|Allowed Loss| C{"2. At-Risk Limitation"} C -->|Excess| SuspAtRisk["Suspended until at-risk is restored (Offsets gain on disposal)"] C -->|Allowed Loss| D{"3. Passive Activity Loss (PAL)"} D -->|Excess| SuspPAL["Suspended to offset future passive income (Fully deductible on disposal)"] D -->|Allowed Loss| E{"4. Excess Business Loss (EBL)"} E -->|Excess > Annual Threshold| NOL["Carried forward as NOL"] E -->|Allowed Loss| Deduct["Fully Deductible Loss in Current Year"]

Rental Real Estate Active Participation Exception

  • Taxpayers can deduct up to $25,000 of rental real estate loss if the owner actively participates and owns at least 10%.
  • The $25,000 allowance starts phasing out when the taxpayer's MAGI exceeds $100,000 and is fully eliminated when MAGI exceeds $150,000.

Real Estate Professional Exception

Rental real estate activities are treated as active trades or businesses (exempt from PAL limitations) if:

  • More than 50% of the taxpayer's personal services are performed in real property trades or businesses; AND
  • Taxpayer performs more than 750 hours of service in real property trades or businesses during the tax year; AND
  • Taxpayer materially participates in each rental real estate activity.

Executive & Equity Compensation Planning

Comprehensive tax comparison across all statutory and nonstatutory equity compensation vehicles.

Vehicle Tax at Grant Tax at Exercise / Vest Tax at Sale of Stock Employer Deduction
Incentive Stock Options (ISOs) None None for Regular Tax.
AMT Adjustment: FMV − Strike Price
Long-Term Capital Gain if held ≥ 2 yrs from grant & ≥ 1 yr from exercise. No deduction (unless disqualifying disposition).
Employee Stock Purchase Plans (ESPPs) None None Ordinary Income on discount spread + Remainder is Capital Gain. No deduction (unless disqualifying disposition).
NQSO (No Readily Determinable FMV) None Ordinary Income:
FMV − Strike Price
Capital Gain:
Sale Price − FMV at Exercise
Deductible at exercise equal to ordinary income recognized.
Restricted Stock Units (RSU) None Ordinary Income at Vesting: FMV at Vesting Date Capital Gain:
Sale Price − FMV at Vesting
Deductible at vesting equal to ordinary income recognized.
Restricted Stock Awards (RSA) with Section 83(b) Ordinary Income: FMV at Grant Date (if §83(b) filed). None at Vesting Capital Gain:
Sale Price − FMV at Grant (Holding period starts at grant).
Deductible at grant equal to §83(b) income recognized.

Statutory Plan Qualification Rules

  • Incentive Stock Option Limits: Max $100,000 of ISOs first exercisable in any calendar year. Strike price ≥ FMV at grant. Employee cannot own > 10% of voting power (unless strike ≥ 110% FMV and 5-yr exercise limit).
  • Employee Stock Purchase Plan Limits: Strike price cannot be less than 85% of lesser of FMV at grant or FMV at exercise. Max $25,000 FMV of stock acquired per calendar year.
  • Section 83(b) Election Rules: Must be filed with the IRS within 30 days of property grant. Converts all future appreciation into LTCG. Risk: If stock is subsequently forfeited, no deduction or loss is allowed for taxes paid.

Alternative Minimum Tax (AMT)

A separate tax system ensuring high-income individuals pay a baseline minimum tax. It adds back certain preferences and adjusts regular taxable income.

Item Category Treatment Common Examples
Adjustments Can be positive (+) or negative (-)
  • Passive activity losses (recalculated)
  • Accelerated depreciation difference (post-1986)
  • State and local taxes (SALT) deducted (Added back)
  • Standard deduction (Added back)
Preferences Always positive (+)
  • Private activity bond interest (normally tax-exempt)
  • Percentage depletion over adjusted basis
  • Pre-1987 accelerated depreciation

Gift Taxation & Unified Transfer Tax

The federal gift tax is paid by the donor. It operates under a unified transfer tax system covering both lifetime gifts and estate transfers.

Exclusions & Thresholds

Limit Type Statutory Standard Tax Impact
Lifetime Unified Exclusion Statutory Unified Lifetime Transfer Exemption Exceeding this amount across a lifetime triggers actual gift/estate tax liability.
Annual Exclusion Statutory Annual Gift Tax Exclusion Amount per donee
(2 × exclusion if split with spouse)
Gifts under this amount are ignored. Gifts over this amount require filing Form 709 and reduce the lifetime exclusion balance.

Unlimited Exclusions (No Gift Tax Triggered)

  • Payments made directly to an educational institution for tuition (not room and board).
  • Payments made directly to a medical provider for healthcare.
  • Transfers to a spouse (marital deduction).
  • Transfers to qualified charities.

Basis of Gifted Property (The Dual-Basis Rule)

Normally, the recipient takes the donor's carryover basis. However, to prevent taxpayers from transferring tax losses to family members, the dual-basis rule kicks in if the property has lost value before it was gifted.

graph TD Start["Gifted Property Basis"] --> Check{"FMV vs. Donor's Basis
at Date of Gift"} Check -->|FMV ≥ Donor's Basis| Carryover["Standard Rule
Recipient uses Donor's Carryover Basis"] Check -->|FMV < Donor's Basis| Dual{"Dual-Basis Rule Applies
What is the Future Sale Price?"} Dual -->|Sale Price > Donor's Basis| Gain["Use Donor's Basis
(Recognize Gain)"] Dual -->|Sale Price < FMV| Loss["Use FMV at Date of Gift
(Recognize Loss)"] Dual -->|"Between FMV and Donor's Basis"| NoGL["No Gain or Loss Recognized"]

Imputed Interest on Below-Market Loans

Under the below-market loan rules, when a lender makes a loan at an interest rate below the Applicable Federal Rate (AFR), the forgone interest is imputed: it is treated as a taxable gift from the lender to the borrower, and as taxable interest income retransferred from the borrower back to the lender.

$$ \text{Imputed Interest} = (\text{Loan Principal} \times \text{Applicable Federal Rate}) - \text{Interest Stated / Payable} $$
Loan Size Limitation / Exception
≤ $10,000 De Minimis Exception: No imputed interest calculated (unless the loan is used to purchase income-producing assets).
≤ $100,000 NII Limit: Imputed interest is capped at the borrower's Net Investment Income (NII) for the year. If the borrower's NII is ≤ $1,000, the imputed interest is exactly $0.

Form 706 Gross Estate & Alternate Valuation Date

  • Gross Estate Inclusions: Worldwide FMV of all assets owned or controlled at death, including:
    • All property owned directly at death.
    • Revocable transfers and retained life estates.
    • 50% of qualifying spousal joint tenancy property.
    • Life insurance proceeds if the decedent possessed incidents of ownership or transferred the policy within 3 years of death.
  • Alternate Valuation Date (AVD): Executor can elect to value all estate assets 6 months after death (or date of distribution/sale, if earlier).
    Dual Reduction Rule: Can ONLY be elected if it decreases both the total Gross Estate value AND the total estate tax liability.

Gift Tax Present Interest Rule & Crummey Trusts (Form 709)

  • Present Interest Requirement: The statutory annual gift exclusion applies only to gifts of a present interest (immediate possession/enjoyment). Gifts of future interests (trust accumulations, remainder interests) are fully subject to gift tax reporting on Form 709.
  • Crummey Trust Powers: Adding a Crummey power gives trust beneficiaries a limited window (e.g., 30–60 days) to withdraw annual trust contributions, converting what would be a future interest into a qualifying present interest eligible for the annual gift exclusion.
  • Generation-Skipping Transfer Tax (GSTT): Imposes a flat 40% tax on transfers made to "skip persons" (beneficiaries ≥ 2 generations below donor, e.g., grandchildren), assessed in addition to regular gift or estate tax.

Personal Financial Planning: Retirement & Education

Backdoor Roth IRA Mechanics & Pro-Rata Aggregation Rule

High-income taxpayers who exceed Roth IRA income phaseouts contribute non-deductible funds to a Traditional IRA and convert to a Roth IRA. Under the pro-rata aggregation rule, the IRS treats all Traditional, SEP, and SIMPLE IRAs as a single aggregate pool on December 31:

Nontaxable Percentage of Conversion

$$\text{Nontaxable \%} = \frac{\text{Total Non-Deductible Basis Across All Non-Roth IRAs}}{\text{Total FMV of Non-Roth IRAs (Dec 31)} + \text{CY Distributions} + \text{CY Conversions}}$$

Taxable Conversion Income

$$\text{Taxable Conversion Income} = \text{Conversion Amount} \times (1 - \text{Nontaxable \%})$$

Employer-Sponsored & Self-Employed Retirement Plans Summary

Plan Type Eligible Entities Statutory Contribution Limits Key Tax Characteristics
SEP IRA Self-employed & small business employers Lesser of Statutory Annual Limit or 25% of compensation (20% of net SE earnings after ½ SE tax deduction). Employer-only contributions; fully deductible; 100% immediate vesting.
SIMPLE IRA Employers with ≤ 100 employees Employee deferral: Up to Statutory Deferral Limit (plus statutory catch-up if age 50+). Mandatory 3% dollar-for-dollar employer match OR 2% non-elective contribution.
Solo 401(k) Owner-only businesses with no common-law staff Employee deferral up to statutory limit + Employer up to 25% profit share (~20% for unincorporated sole proprietors) up to combined statutory maximum. Allows pre-tax and designated Roth elective deferral options.

Required Minimum Distributions (RMDs, SECURE 2.0 Act)

  • Mandatory Starting Age: Age 73 for those born 1951–1959, rising to Age 75 for those born in 1960 or later (or retirement if later and not a > 5% owner of a workplace plan; Roth IRAs and Roth 401(k)s are exempt). First RMD may be delayed to April 1 of the following year; subsequent RMDs are due by December 31.
  • Excise Penalty: 25% excise tax on the shortfall (reducible to 10% if corrected timely within 2 year).

Annuities & Life Insurance Risk Mitigation

  • Annuities: Earnings grow tax-deferred. Mitigates longevity risk. Distributions represent a pro-rata mix of return of capital (nontaxable) and earnings (taxable).
  • Life Insurance: Premiums are nondeductible; death benefit proceeds are generally income-tax-free. Frequently utilized to provide liquidity for estate taxes.

Comprehensive Education Savings Vehicles Comparison

Vehicle Contribution Limits Growth & Qualified Distributions Special Strategic Rules
Section 529 Qualified Tuition Plan No annual federal limit (subject to gift tax rules and aggregate state plan caps). Earnings grow tax-free; distributions tax-free for qualified higher education and up to $10,000/yr for K-12 tuition.
  • 5-Yr Front Loading: Contribute up to 5 × Annual Gift Exclusion gift-tax free.
  • SECURE 2.0 Roth Rollover: Up to $35,000 lifetime rolled to beneficiary's Roth IRA (plan open ≥ 15 yrs).
Coverdell ESA Statutory annual limit per beneficiary (subject to MAGI phaseouts). Earnings grow tax-free; distributions tax-free for K-12 and higher education expenses. Must be fully distributed by beneficiary age 30 (or transferred to eligible family member under 30).
Series EE / I U.S. Savings Bonds Annual Treasury purchase limits. Interest excluded from income if used for higher education tuition/fees. Purchaser must be at least age 24 prior to bond issue date. Subject to MAGI phaseouts.
Student Loan Interest Deduction Above-the-line deduction up to the statutory maximum. Deduction phases out at higher MAGI tiers; not allowed if Married Filing Separately. Applies to interest paid on qualified higher education loans for taxpayer, spouse, or dependent.

Estate Considerations (Beneficiaries)

Beneficiary designations on retirement accounts and life insurance policies supersede instructions in a will. Inherited assets receive a "stepped-up" basis to FMV at the date of death.

Other Individual Tax Topics

Kiddie Tax

Prevents parents from shifting investment income to children. A dependent child's standard deduction is limited to the greater of:

$$ \max(\$1,350, \text{Earned Income} + \$450) $$

Net unearned income in excess of $2,700 is taxed at the parent's marginal rate.

Healthcare Savings Accounts

Feature FSA (Flexible Spending Account) HSA (Health Savings Account)
Eligibility Employer-sponsored. Must have a High Deductible Health Plan (HDHP).
Rollover "Use it or lose it" (max $680 carryover). Funds accumulate year-over-year and are portable.
Max Contribution $3,400 $4,400 (Self) / $8,750 (Family) + $1,000 Age 55+ catch-up.

Estimated Tax Payments & Safe Harbors

Taxpayers must make quarterly prepayments if they expect to owe $1,000 or more. Safe harbor requires the lesser of:

  • 90% of the Current Year (CY) tax liability.
  • 100% of the Prior Year (PY) tax liability (or 110% if PY AGI was > $150,000).

Charitable Contributions & AGI Limits

Non-Itemizer Above-the-Line Cash Deduction

  • $1,000 Cap: Maximum cash deduction for Single and Married Filing Separately taxpayers taking the standard deduction.
  • $2,000 Cap: Maximum cash deduction for Married Filing Jointly taxpayers taking the standard deduction.
  • Qualifying Donations: Must be cash paid directly to qualified public charities (contributions to Donor-Advised Funds and private foundations do not qualify).

Itemizer Deductions & 0.5% AGI Floor

Taxpayers who itemize on Schedule A are subject to a 0.5% AGI deduction floor across total charitable giving. Only contributions in excess of 0.5% of AGI are deductible.

$$ \text{Allowable Itemized Deduction} = \max\Big(0, \text{Total Eligible Contributions} - (0.005 \times \text{AGI})\Big) $$

AGI Ceilings for Itemized Contributions

After applying the 0.5% floor, total annual deductions are capped at the following AGI percentage ceilings:

Type of Property Donated AGI Ceiling Limit Valuation & Provisions
Cash 60% of AGI Permanent 60% cap for direct cash gifts to public charities.
Ordinary Income Property (Short-term assets, inventory) 50% of AGI Deduction limited to the lesser of Adjusted Basis or FMV.
Long-Term Capital Gain (LTCG) Property 30% of AGI Deductible at full Fair Market Value (FMV) without triggering capital gains tax.

Carryover Rules & Benefit Caps

  • 5-Year Carryover: Unused excess contributions above the AGI ceilings can be carried forward for up to 5 consecutive tax years (subject to the 0.5% floor in carryover years).
  • 35% High-Income Cap: Taxpayers in the 37% top marginal tax bracket have itemized charitable deduction tax savings capped at a maximum 35% benefit rate.

Valuation of Noncash Property

graph TD Start["Type of Property Donated"] --> Ord["Ordinary Income Property"] Start --> LTCG["Long-Term Capital Gain Property"] Ord --> DeductOrd["Deduction = Lesser of Adjusted Basis or FMV"] LTCG --> Use{"How will charity use it?"} Use -->|Related to exempt purpose| DeductFMV["Deduction = FMV"] Use -->|Unrelated to exempt purpose| DeductBasis["Deduction = Limited to Adjusted Basis"]

Risk Management & Investment Analysis

Risk Mitigation Strategies

Loss Severity Frequency Method
High High Risk Avoidance: Remove the risk entirely.
Low High Risk Reduction: Decrease the severity/frequency.
Low Low Risk Retention: Absorb the risk internally.
High Low Risk Transfer: Shift risk to another party (e.g., Insurance).

Types of Risk

  • Nonsystematic (Diversifiable): Unique to a certain firm/industry; can be mitigated by diversifying investments.
  • Systematic (Market): Affects the entire market (e.g., inflation, interest rates); cannot be diversified away, but can be hedged via derivatives.

Investment Formulas

Return on Investment (ROI)

$$ \text{ROI} = \frac{\text{Sales Price} - \text{Cost of Investment}}{\text{Cost of Investment}} $$

After-Tax Rate of Return (ATRR)

$$ \text{After-Tax Rate of Return (ATRR)} = \text{ROI} \times (1 - \text{Tax Rate}) $$

The One Big Beautiful Bill Act (OBBBA)

Key Individual Provisions (2026+)

Provision Updated Rule / Threshold
Standard Deduction $16,100 (Single/MFS), $32,200 (MFJ), $24,150 (HoH). Includes a $6,000 bonus deduction for qualifying seniors.
Child Tax Credit $2,200 per child (with up to $1,700 refundable)
SALT Cap Raised from $10,000 to $40,000 (for taxpayers earning < $500k)
New Deductions
  • Tips: Up to $25,000 tax-free.
  • Overtime Pay: $12,500 deduction ($25,000 for MFJ).
  • Auto Loans: $10,000 interest deduction for new, U.S.-assembled vehicles.
Trump Accounts New tax-deferred accounts parents can create for the benefit of their children. The contribution limit is up to $5,000 per tax year.

Key Business Provisions (2026+)

  • Bonus Depreciation: Permanently restored to 100% for qualifying property.
  • Research & Experimentation (R&E): Immediate expensing for domestic R&E costs.
  • Executive Compensation: The $1M limit on deductible compensation is expanded to all members of a covered corporation's controlled group.

Entity Tax Compliance & Planning (C Corps)

C Corporation Formation

Section 351 Tax-Free Formation

No gain or loss is recognized upon formation if the contributing shareholders own at least 80% of the corporation immediately after the transfer. However, gain is recognized if "boot" (cash) is received, or if liabilities assumed by the corp exceed the shareholder's basis.

C Corp Formation (Corporation's Books)
Cash Received$XX
Property (Carryover Basis)$XX
Liability Assumed$XX
Common Stock (Par)$XX
Additional Paid-In Capital$XX
Corp's basis in property = Shareholder's adjusted basis + any gain recognized by the shareholder.

Shareholder's Basis in Stock Received:

$$ \begin{aligned} &\text{Cash Contributed} \\ + \; &\text{NBV of Property Contributed} \\ - \; &\text{Debt on Property Assumed by Corp} \\ + \; &\text{FMV of Services Provided (taxed as ordinary income)} \\ + \; &\underline{\text{Gain Recognized by Shareholder}} \\ = \; &\textbf{Shareholder Basis} \end{aligned} $$

Corporate Distributions & Liquidation

Nonliquidating Corporate Distributions

Distributions follow a strict order of taxation based on Earnings and Profits (E&P):

graph TD Start["Corporate Distribution"] --> EP["Bucket 1: Current & Accumulated E&P"] EP -->|Amount up to E&P| Div["Taxable Dividend Income"] EP -->|Excess| Basis["Bucket 2: Shareholder Stock Basis"] Basis -->|Amount up to Basis| Nontax["Nontaxable Return of Capital (Reduces Basis)"] Basis -->|Excess| CG["Bucket 3: Remaining Excess"] CG -->|All remaining| TaxCG["Taxable Capital Gain"]

Property Distributions: If a C Corp distributes appreciated property, it recognizes a gain as if the property was sold at FMV. It cannot recognize a loss on depreciated property.

Taxable Complete Liquidation vs. Tax-Free 80% Subsidiary Liquidation

Attribute Taxable Liquidation
(Individual / Non-80% Owner)
80% Subsidiary Liquidation
(Parent Corporate Owner)
Corporate Gain / Loss Corporation recognizes full gain and loss as if assets were sold at FMV. No gain or loss recognized by liquidating subsidiary on distributions to 80% parent.
Shareholder Gain / Loss Shareholder recognizes capital gain/loss:
Gain / Loss = (FMV Assets Received − Liabilities Assumed) − Stock Basis
No gain or loss recognized by parent corporation upon receipt of subsidiary assets.
Asset Basis to Shareholder Stepped-Up Basis: Assets received take a new basis equal to their FMV at distribution date. Carryover Basis: Parent takes subsidiary's inside adjusted basis in all distributed assets.
Tax Attribute Inheritance All tax attributes (NOLs, capital loss carryovers, E&P balances) are permanently extinguished. All tax attributes (NOL carryforwards, capital loss carryforwards, E&P) transfer to the parent.

Corporate Reorganizations

Corporate reorganizations allow corporations and their shareholders to restructure or combine entities without immediate tax recognition, provided the transaction meets strict statutory and judicial requirements.

Judicial Requirements for Tax-Free Treatment

  • Continuity of Proprietary Interest (COI): Target shareholders must receive significant equity (generally ≥ 40% of total consideration) in the acquiring corporation.
  • Continuity of Business Enterprise (COBE): Acquiring entity must continue Target's historic business or use a significant portion of Target's historic assets.
  • Valid Business Purpose: Restructuring must have a substantial non-tax economic justification.
  • Step-Transaction Doctrine: Form of formally separate steps will be integrated into a single transaction to determine true tax substance.

Summary Comparison of Reorganization Types (A through F)

Type Description Statutory Mechanics & Consideration Boot & Tax Consequences
Type A Statutory Merger or Consolidation Target merges into Acquiring under state corporate law. Substantial stock required (COI ≥ 40%). Boot triggers recognized gain up to boot received. Loss is not recognized.
Type B Stock-for-Stock Acquisition Acquiring gains control (≥ 80% voting & ≥ 80% all other shares) of Target solely for Acquiring voting stock. Zero Boot Allowed: Any cash consideration invalidates entire Type B tax-free status.
Type C Stock-for-Assets Acquisition Acquiring acquires "substantially all" assets (70% gross / 90% net) of Target solely for voting stock. Target must liquidate. Boot allowed up to 20% of total consideration (liabilities assumed count as boot if other boot given).
Type D Divisive Restructuring (Spin-off, Split-off, Split-up) Transfer of assets to controlled sub followed by distribution of sub stock. Requires 5-year active trade/business history. Nontaxable if statutory control (≥ 80%) and distribution tests are fully satisfied.
Type E Recapitalization Internal restructuring of a single corporation's capital structure (e.g., exchanging old bonds for new stock). No gain/loss unless principal amount of securities received exceeds securities surrendered.
Type F Change in Form / Identity Mere change in identity, form, or state of incorporation of a single corporation (e.g., reincorporation). Completely tax-free; all corporate tax attributes and tax year continue seamlessly.

Tax Consequences & Basis Calculations

Shareholder Stock Basis
$$ \text{Stock Basis} = \text{Basis Surrendered} + \text{Gain Recognized} - \text{Boot Received} $$
Acquiring Corporation Asset Basis
$$ \text{Asset Basis} = \text{Target Inside Basis} + \text{Gain Recognized by Target} $$

Corporate Losses & Utilization

Type of Loss Offset Rules Carryback / Carryforward
Capital Losses Can only offset capital gains (not ordinary income). Carryback 3 years, carryforward 5 years.
Net Operating Losses (NOLs) Can offset ordinary income. Post-2020 NOL deductions are limited to 80% of taxable income in the carryforward year. No carryback allowed. Carryforward is indefinite.

Section 382 Limitation (Change in Ownership)

If there is an ownership change of more than 50% by 5% shareholders over a 3-year testing period, the ability to use existing NOL carryforwards is severely limited annually.

$$ \text{Annual Sec. 382 Limit} = \text{Long-Term Tax-Exempt Rate} \times \text{Value of Old Loss Corporation} $$

Corporate Compliance: Penalty Taxes, Estimated Taxes & Shareholder Loans

Corporate Penalty Taxes (AET & PHC)

Penalty taxes are imposed at a flat 20% rate (in addition to the standard 21% corporate income tax) to penalize improper retention of corporate earnings or passive income sheltering.

Feature Accumulated Earnings Tax (AET) Personal Holding Company Tax (PHC)
Triggering Condition Accumulating E&P beyond the reasonable present and anticipated needs of the business. Closely held C corporation holding predominantly passive investment income assets.
Statutory Tests Subjective IRS audit determination. Assessed if accumulation exceeds statutory lifetime minimum credits:
  • $250,000 for regular operating C corps.
  • $150,000 for personal service corps.
Objective 2-Part Statutory Test:
  1. Stock Ownership Test: > 50% of stock value owned by ≤ 5 individuals during the last half of the tax year.
  2. Passive Income Test: ≥ 60% of Adjusted Ordinary Gross Income (AOGI) is passive PHC income (Net rent, Interest, Royalties, Dividends).
Avoidance & Planning Document specific, definite, and feasible business expansion plans. Pay dividends. Distribute current earnings as dividends (or consent / deficiency dividends).

Corporate Estimated Tax Payments (Form 1120-W)

A C corporation must make quarterly estimated tax payments if its estimated annual tax liability is expected to be $500 or more.

Taxpayer Category Required Annual Payment (Safe Harbor Rules)
Small / Regular Corporations Lesser of:
  • 100% of Current Year Tax Liability, OR
  • 100% of Prior Year Tax Liability (must cover 12 months with positive tax).
Large Corporations
(Taxable Income ≥ $1,000,000 in any of prior 3 yrs)
Must pay 100% of Current Year Tax Liability.
Exception: Prior Year safe harbor can be used for the first quarterly installment only; any shortfall must be fully made up in the second installment.

Corporate / Shareholder Below-Market Loans

Loan Type Tax Treatment to Corporation Tax Treatment to Shareholder
Corporation to Employee-Shareholder Deductible compensation expense + Taxable interest income. Taxable compensation income (W-2 wages) + Deemed interest expense.
Corporation to Non-Employee Shareholder Nondeductible dividend distribution + Taxable interest income. Taxable dividend income + Deemed interest expense.

International Corporate Tax Concepts

Focuses on general concepts of income sourcing and structure, rather than specific foreign treaties.

Sourcing of Income

Income Type Sourcing Rule
Interest & Dividends Sourced to the residence/location of the payor.
Personal Services Sourced where the services are physically performed.
Rents & Royalties Sourced where the property is located or used.
Sale of Real Property Sourced where the property is located.

Foreign Branch vs. Foreign Subsidiary

  • Foreign Branch: An unincorporated extension of the domestic corporation. Income is taxed immediately in the U.S. as earned, and the entity claims a Foreign Tax Credit (FTC) for host country taxes.
  • Foreign Subsidiary: A separate legal entity incorporated abroad. Income is generally deferred from U.S. taxation until repatriated, unless caught by anti-deferral rules (like Subpart F).

Permanent Establishment (PE)

A fixed place of business (e.g., office, factory) in a foreign country through which business is carried on. Creating a PE generally subjects the entity to corporate income tax in that foreign jurisdiction.

Controlled Foreign Corporation (CFC)

A foreign corporation where > 50% of voting power or value is owned by U.S. shareholders (who each own 10%+). Subject to Subpart F rules, which force U.S. shareholders to currently recognize certain passive or highly mobile foreign income, even if not distributed as a dividend.

Foreign Tax Credit (FTC) Limitation Formula & Separate Baskets

To prevent taxpayers from using foreign tax credits to offset U.S. tax on domestic-source income, the FTC is limited to the lesser of actual foreign taxes paid or the statutory limitation:

Foreign Tax Credit Limitation
$$ \text{FTC Limitation} = \left( \frac{\text{Foreign-Source Taxable Income}}{\text{Total Worldwide Taxable Income}} \right) \times \text{Pre-Credit U.S. Tax} $$
  • Mandatory Separate Baskets: The limitation must be calculated separately for:
    1. Passive Category Income: Dividends, interest, royalties, annuities, capital gains.
    2. General Category Income: Active foreign trade or business operating income.
    3. Foreign Branch Income: Operational income derived directly through foreign branch operations.
  • Carryover Rules: Excess FTC can be carried back 1 year and carried forward 10 years.
  • Participation Exemption (100% Foreign DRD): Domestic C corporations owning ≥ 10% of a foreign subsidiary can claim a 100% Dividends Received Deduction for the foreign-source portion of dividends repatriated to the U.S.

Consolidated Tax Returns

An affiliated group can elect to file a single, consolidated federal income tax return. Once elected, this filing status is generally binding for all future years.

The 80% Affiliated Group Test

To qualify, a parent corporation must directly own ≥80% of the voting power AND ≥80% of the total value of the stock of at least one includible subsidiary.

  • Losses of one subsidiary can offset the profits of another.
  • Brother-sister corporations (two separate corporations owned by the same individual shareholder) do not qualify as an affiliated group.

Consolidated Taxable Income Computation

Instead of a single calculation, consolidated income is determined through a 5-step adjustment process:

Action Details
1. Separate Incomes Calculate the standalone taxable income for each member of the group.
2. Remove Group Items Back out items that must be evaluated at the consolidated level (e.g., Capital Gains/Losses, Sec. 1231 gains/losses, Charitable Contributions, and the Dividends Received Deduction).
3. Eliminate Intercompany Remove intercompany dividends, loans, and sales.
Note: Gains or losses on intercompany asset sales are deferred until the asset is sold to an outside party.
4. Combine Sum the adjusted separate taxable incomes from Step 3 to create a baseline group income.
5. Apply Group Limits Re-apply the consolidated items removed in Step 2, now calculated based on the combined group's limits, to arrive at final Consolidated Taxable Income.

State & Local Taxation (SALT) for Corporations

Nexus & Jurisdiction

Nexus: The minimum degree of connection between a business and a state that subjects the business to the state's tax jurisdiction. Can be physical (property, employees) or economic (exceeding state-defined sales thresholds).

Allocation vs. Apportionment

Concept Application Income Type
Allocation Assigned entirely and directly to a specific state. Nonbusiness Income: Passive income (interest, dividends, rents, capital gains not related to primary operations).
Apportionment Divided among multiple states using a formula. Business Income: Income derived from the regular, primary course of trade or business.

Standard Apportionment Formula

Historically equally weighted, but many states now heavily or solely weight the Sales Factor.

Equal-Weighted Three-Factor Apportionment
$$ \text{State Apportionment \%} = \frac{\left( \frac{\text{State Sales}}{\text{Total Sales}} \right) + \left( \frac{\text{State Payroll}}{\text{Total Payroll}} \right) + \left( \frac{\text{State Property}}{\text{Total Property}} \right)}{3} $$

Public Law 86-272: Federal Statutory Nexus Immunity

Public Law 86-272 prevents a state from imposing a net income tax on an out-of-state corporation if the corporation's only business activity within the state meets all three statutory conditions:

Protected Activities (Immune from Net Income Tax)
  • Soliciting orders for sales of tangible personal property only.
  • Orders sent outside the state for approval or rejection.
  • Orders filled by shipment from a point outside the state.
  • Carrying promotional samples without sales from stock.
Unprotected Activities (Triggers Income Tax Nexus)
  • Making sales of services or real/intangible property.
  • Maintaining an office, warehouse, or retail location in state.
  • Performing post-sale repair, warranty, or installation services.
  • Collecting delinquent accounts or investigating credit.
  • Consigning inventory to third parties in the state.

Note: P.L. 86-272 protects strictly against Net Income Taxes. It does NOT protect against Sales/Use taxes, Gross Receipts taxes (e.g., Washington B&O, Ohio CAT), or franchise net worth taxes.

Flow-Through Entity Compliance & Planning

Partnership Formation

Contribution of Property

Generally tax-free for both the partner and the partnership. Pre-contribution built-in gains/losses on property are allocated to the contributing partner upon a subsequent sale by the partnership.

Partnership Formation (Partnership's Books)
Property (Carryover Basis)$XX
Cash$XX
Liability Assumed$XX
Partner Capital Account$XX
  • Contribution of Services: A partner must recognize ordinary income equal to the FMV of the partnership interest received in exchange for services.
  • Property with Excess Liability: A partner recognizes a taxable capital gain if they contribute property subject to a liability, and the portion of the liability assumed by the other partners exceeds the contributing partner's basis.

Partnership Basis & Elections

Basis Terminology

Type Definition / Debt Impact
Outside Basis The partner's tax basis in their partnership interest.
Inside Basis The partnership's tax basis in its actual assets.
Recourse Debt Partner has personal liability. Increases outside basis only for general partners (or those who guarantee it).
Nonrecourse Debt Secured only by property. Increases outside basis for all partners based on profit-sharing ratios.

Adjustments to Outside Basis

$$ \begin{aligned} &\text{Initial Basis (Cash + Property NBV - Liabilities Assumed by Others)} \\ + \; &\text{Additional Contributions} \\ + \; &\text{Share of Ordinary Income \& Separately Stated Items} \\ + \; &\text{Increase in Share of Partnership Debt} \\ - \; &\text{Distributions (Cash, then Property Adj. Basis)} \\ - \; &\text{Decrease in Share of Partnership Debt} \\ - \; &\underline{\text{Share of Ordinary Loss \& Nondeductible Expenses}} \\ = \; &\textbf{Ending Outside Basis} \text{ (Never below zero)} \end{aligned} $$

Section 754 Optional Basis Adjustments (Transfers vs. Distributions)

Adjustment Type Section 743(b) (Sale or Death) Section 734(b) (Distributions)
Scope of Adjustment Applies to the transferee (purchasing) partner only. Applies to the entire partnership (inside basis of remaining retained assets).
Formula Basis Adjustment = Transferee Outside Basis − Transferee's Share of Inside Basis Basis Adjustment = Distributee Gain Recognized + Basis Step-Down of Distributed Property
Mandatory Threshold Mandatory if partnership has a Substantial Built-in Loss (> $250,000) at transfer date. Mandatory if distribution results in a Substantial Basis Reduction (> $250,000).

Partnership Distributions & Liquidation

Nonliquidating Distributions

Generally nontaxable. Distributions reduce the partner's outside basis (cash first, then property). A gain is only recognized if cash distributed exceeds the partner's entire outside basis. Losses are never recognized.

Liquidating Distributions

Generally nontaxable. The partner's remaining outside basis (after cash) is fully allocated to the property received to zero out the partner's interest. A loss is recognized only if the distribution consists solely of cash, unrealized receivables, and inventory, and their inside basis is less than the partner's outside basis.

Multi-Property Distribution Basis Allocation

Scenario Mandatory Statutory Allocation Steps
Outside Basis < Inside Basis
(Basis Step-Down)
  1. Assign initial basis to distributed assets equal to the partnership's inside adjusted basis.
  2. Reduce basis of depreciated assets down to their fair market value.
  3. Allocate remaining required basis reduction among all assets in that class based on their relative adjusted bases (after prior step).
Outside Basis > Inside Basis
(Liquidating Step-Up)
  1. Assign initial basis to distributed assets equal to the partnership's inside adjusted basis.
  2. Increase basis of appreciated assets up to their fair market value.
  3. Allocate remaining required basis increase among all assets in that class based on their relative FMVs.

Sale of Partnership Interest, Section 751 Assets & Disguised Sales

Sale of Partnership Interest & Section 751 "Hot Assets"

When a partner sells their interest, the transaction is treated as the sale of a capital asset, except to the extent of the selling partner's share of Section 751 Assets (Unrealized Receivables and Inventory Items), which trigger ordinary income.

Total Amount Realized

$$ \text{Total Amount Realized} = \text{Cash} + \text{FMV of Property Received} + \text{Relief of Debt Share} $$

Total Realized Gain / Loss

$$ \text{Total Realized Gain / Loss} = \text{Total Amount Realized} - \text{Adjusted Outside Basis} $$

Section 751 Ordinary Income

$$ \text{Section 751 Ordinary Income} = \text{Selling Partner's Share of Built-in Gain in Section 751 Assets} $$

Remaining Capital Gain / Loss

$$ \text{Remaining Capital Gain / Loss} = \text{Total Realized Gain / Loss} - \text{Section 751 Ordinary Income} $$

Definition of Section 751 Assets (Unrealized Receivables & Inventory)

  • Unrealized Receivables: Rights to payment for goods or services not previously included in income (cash-basis A/R) plus §1245 and §1250 depreciation recapture potential.
  • Inventory Items: Traditional inventory, raw materials, supplies, and all other non-capital/non-§1231 business assets.

Disguised Sales of Property

If a partner transfers property to a partnership and receives a related distribution of money or property within a 2-year window (before or after), the transaction is statutorily presumed to be a taxable disguised sale rather than a tax-free contribution and distribution.

S Corp Operations & Distributions

Separately Stated Items

Items not aggregated at the corporate level, passed through separately on Schedule K-1:

  • Rental Real Estate: Income/loss is passive.
  • Portfolio Income: Interest, dividends, and royalties.
  • Net Section 1231 Gain/Loss: Evaluated at the shareholder level.
  • Charitable Contributions: Subject to individual AGI limits.
  • Section 179 Expense: Subject to individual limits.
  • Tax-Exempt Interest: Increases stock basis (OAA) but is not taxable.

S Corporation Stock Basis Ordering

Stock basis cannot be reduced below zero. Adjustments must be calculated in this exact statutory sequence:

Adjustment Ordering Impact & Limitations
1. Beginning Stock Basis Carried over from prior year ending balance.
2. (+) Capital Contributions & All Income Items Ordinary business income + Separately stated income/gains + Tax-exempt income.
3. (−) Distributions to Shareholders Nontaxable return of basis (reduces stock basis before expenses and losses).
4. (−) Nondeductible, Noncapital Expenses Fines, penalties, 50% non-deductible meals, expenses related to tax-exempt income.
5. (−) Deductible Losses and Deductions Ordinary business loss + Separately stated deductions (§179, charitable, capital losses).
= Ending Stock Basis Stock basis is floored at $0. Excess losses spill over to Direct Debt Basis.

Direct Debt Basis & Basis Restoration Mechanics

  • Direct Loans Only: Debt basis is established only by direct loans made by the shareholder to the S corporation. Guaranteeing third-party bank debt creates zero debt basis.
  • Loss Utilization Sequence: Losses first reduce stock basis to $0, then reduce direct debt basis to $0. Any remaining loss is suspended indefinitely.
  • Basis Restoration Rule: In subsequent profitable years, net positive adjustments first restore direct debt basis back to its original face value before any increase is made to stock basis.
  • Permanent Loss on Sale: Suspended S corp losses due to lack of basis are permanently lost if the shareholder disposes of all stock (unlike passive activity losses which unlock upon a complete taxable disposition).

Accumulated Adjustments Account (AAA)

Tracks undistributed tax-paid earnings. Distributions from AAA are tax-free. AAA can go negative from losses, but a distribution cannot drop AAA below zero.

Distribution Waterfall (With Prior C Corp E&P)

If the S Corp has accumulated E&P from prior C Corp years, statutory distribution ordering follows this 4-tier waterfall:

graph TD Start["S Corp Distribution"] --> AAA["Tier 1:
Accumulated Adjustments Account (AAA)"] AAA -->|Amount up to AAA| Nontax1["Nontaxable (Reduces Stock Basis)"] AAA -->|Excess| EP["Tier 2:
Prior C Corp Accumulated E&P"] EP -->|Amount up to E&P| TaxDiv["Taxable Ordinary Dividend Income"] EP -->|Excess| Basis["Tier 3:
Remaining Stock Basis (OAA / Basis)"] Basis -->|Amount up to Basis| Nontax2["Nontaxable Return of Capital (Reduces Basis to Zero)"] Basis -->|Excess| CG["Tier 4:
Distributions in Excess of Basis"] CG -->|All remaining| TaxCG["Taxable Capital Gain (LTCG)"]

AAA Bypass Election

An S Corp can elect to distribute C Corp AEP before AAA. This tax planning "bypass election" is utilized to strip out C Corp E&P to avoid the passive investment income tax or the termination of S status.

C-to-S Conversion Transition Taxes

When an existing C corporation elects S corporation status, the tax code imposes three potential entity-level transition taxes to prevent corporate tax avoidance.

Transition Tax Triggering Event Tax Calculation & Rate Payment & Relief Rules
1. Built-In Gains (BIG) Tax Sale or distribution of appreciated assets within 5 years of S election date. 21% Corporate Tax on the lesser of:
  • Recognized Built-in Gain (FMV − Adjusted Basis at conversion)
  • Current Year Taxable Income
Tax paid reduces the flow-through gain passed to shareholders on Schedule K-1.
2. LIFO Recapture Tax C corporation utilizing LIFO inventory converts to S corporation status. Excess of inventory value under FIFO over LIFO basis at conversion date is added to gross income of final C corp return. Tax liability is paid in 4 equal annual interest-free installments (1st due with final Form 1120; remaining 3 with Forms 1120-S). S Corp increases inventory basis.
3. Passive Investment Income Tax S corp has accumulated C corp E&P at year-end AND passive investment income > 25% of gross receipts. 21% Corporate Tax on Excess Net Passive Income. Termination Rule: If passive income > 25% of gross receipts for 3 consecutive years, S status is automatically terminated on Day 1 of Year 4.

Choice of Entity Comparison Matrix

Strategic evaluation of business entity choices across all lifecycle stages from formation to liquidation.

Planning Criterion Sole Proprietorship Partnership / LLC S Corporation C Corporation
1. Tax Return Form Form 1040, Schedule C Form 1065 (Informational) Form 1120-S (Informational) Form 1120 (Corporate)
2. Entity-Level Tax None None None (except Built-In Gains & Passive Income taxes) Flat 21% corporate tax
3. Owner-Level Tax Individual rates (10%–37%) Individual rates (10%–37%) Individual rates (10%–37%) Qualified dividends (0/15/20% + 3.8% NIIT)
4. Self-Employment Tax Planning All net business income subject to 15.3% SE tax. General partners / LLC managers subject to 15.3% SE tax on distributive share. Reasonable salary subject to FICA; distributions are exempt from SE tax. W-2 salary subject to FICA; dividends not subject to SE tax.
5. Property Contributions Tax-free Tax-free; precontribution built-in gain allocated to contributor. Tax-free only if contributing group has ≥ 80% control (Section 351). Tax-free only if contributing group has ≥ 80% control (Section 351).
6. Entity Debt in Basis N/A Yes: Recourse & nonrecourse debt increases outside basis. No: Direct shareholder loans only; bank debt gives $0 basis. No basis impact to shareholders.
7. Business Loss Deductions Immediate against other income (subject to EBL). Flows through (Basis → At-Risk → PAL → EBL). Flows through (Stock/Debt basis → At-Risk → PAL → EBL). Trapped at entity level; carried forward as NOL (80% limit).
8. QBI Deduction (Section 199A) Eligible for up to 20% Eligible for up to 20% Eligible for up to 20% Ineligible
9. Appreciated Property Distributions (Current) Nontaxable Nontaxable: Partner takes carryover inside basis. Taxable gain recognized at entity level and flowed to shareholders. Taxable gain recognized at entity level + Taxable dividend to shareholder.
10. Liquidating Distributions (Property) Nontaxable Nontaxable: Partner takes remaining outside basis. Gain/loss recognized at entity level + Shareholder capital gain/loss. Gain/loss recognized at entity level + Shareholder capital gain/loss.
11. Number / Type of Owners 1 individual only ≥ 2 partners; no restrictions on owner types. Max 100 shareholders; US individuals, estates, certain trusts only. No restrictions on number or types of shareholders.
12. Capital Structure Single owner Flexible special allocations allowed (substantial economic effect required). One class of stock only (voting differences permitted). Multiple classes of common and preferred stock permitted.
13. Most Advantageous Strategy Simplest low-risk startup operations. Optimal for real estate, debt leverage, and asset distributions. Optimal for profitable service businesses minimizing SE tax. Optimal for venture-backed startups retaining profits or Section 1202 QSBS.

Property Transaction Planning

Character of Assets

Capital Assets

Assets held for investment or personal use (e.g., stocks, bonds, personal car, home).

Noncapital (Ordinary) Assets

  • Inventory
  • Accounts Receivable
  • Depreciable property and real estate used in a trade or business held for one year or less.

Section 1231 Assets

Depreciable personal property and real estate used in a trade or business held for more than one year.

Net 1231 Treatment: Net gains are treated as long-term capital gains, while net losses are treated as ordinary losses. A 5-year look-back rule applies: if there is a net Section 1231 gain, it is treated as ordinary income to the extent of any unrecaptured Section 1231 losses from the previous five years.

Section 1231 Netting Hierarchy & 5-Year Lookback Rule

graph TD Start["Net All Current Year Section 1231 Gains & Losses"] --> Check{"Net Gain or Net Loss?"} Check -->|Net Loss| OrdLoss["Treat as Ordinary Loss
(Fully offsets ordinary income without limit)"] Check -->|Net Gain| Lookback{"Apply 5-Year Lookback Rule (§1231(c))
Any nonrecaptured §1231 losses in prior 5 years?"} Lookback -->|Yes| Recapture["Recharacterize Gain as ORDINARY INCOME
up to prior unrecaptured losses"] Lookback -->|No / Remaining Gain| LTCG["Treat as Long-Term Capital Gain (LTCG)"] Recapture --> Ordering["Ordering Rule: Unrecaptured §1250 Gain (25%)
is recaptured as Ordinary FIRST, then regular LTCG"]

Depreciation Recapture

When Section 1231 assets are sold at a gain, the gain must be "recaptured" as ordinary income up to the amount of accumulated depreciation.

Section Applies To Treatment
1245 Depreciable personal property (Machinery, Equipment) Gain is recaptured as ordinary income to the extent of all accumulated depreciation. Any remainder is 1231 gain.
1250 Depreciable real property (Individuals) "Unrecaptured 1250 gain" (portion of gain attributable to straight-line depreciation) is taxed at a maximum rate of 25%.
291 Depreciable real property (C Corps) 20% of the lesser of recognized gain or accumulated straight-line depreciation is recaptured as ordinary income.

Cost Recovery & Depreciation

Taxpayers must recover the cost of business or income-producing property through MACRS.

MACRS Conventions

Convention Application Details
Half-Year Default for personal property. Treats all property placed in service as if it was placed in service in the middle of the year.
Mid-Quarter Triggered when >40% of total personal property is placed in service in the 4th quarter. Assets are grouped by quarter and depreciated from the middle of their respective quarter.
Mid-Month Real property (buildings). Depreciation begins in the middle of the month the property is placed in service.

Accelerated Expensing (OBBBA Updated)

  • 100% Bonus Depreciation: The OBBBA permanently restored bonus depreciation to 100%. Qualifying property (generally MACRS property with a recovery period of 20 years or less) can be fully expensed in the year it is placed in service.
  • Section 179: Allows an immediate deduction of tangible personal property up to a specified limit, but it cannot create or increase a net loss.

Property Realization & Like-Kind Exchanges (§1031)

General Realization & Recognition Formulas

Amount Realized

$$ \text{Amount Realized} = \text{Cash} + \text{FMV of Property/Services} + \text{Debt Assumed by Buyer} $$

Realized Gain / Loss

$$ \text{Realized Gain/Loss} = \text{Amount Realized} - \text{Adjusted Basis} $$

Section 1031 Like-Kind Exchanges (Real Property)

Applies strictly to real property used in trade or business or held for investment. No loss is ever recognized on a like-kind exchange.

Recognized Gain

$$ \text{Recognized Gain} = \min(\text{Realized Gain}, \; \text{Boot Received}) $$

Boot includes cash, non-like-kind property, and net liability relief.

Basis of New Property

$$ \text{Basis of New Property} = \text{FMV of Property Received} - \text{Deferred Gain} + \text{Deferred Loss} $$

Property Nonrecognition & Gain Exclusions

Principal Residence Gain Exclusion (§121)

  • Exclusion Cap: Exclude up to $250,000 (Single / MFS) or $500,000 (MFJ) of capital gain on the sale of a principal residence.
  • Ownership & Use Test: Must own and use the property as a principal residence for at least 2 out of the 5 years preceding the sale. (Both spouses must meet the use test for the $500,000 MFJ limit).
  • Depreciation Recapture: Any depreciation claimed after May 6, 1997 (e.g., home office) is ineligible for exclusion and is taxed as Unrecaptured §1250 Gain at 25%.
  • Nonqualified Use Proration: Periods of nonqualified use (e.g., rental prior to primary residence use) prorate the exclusion.

Involuntary Conversions (§1033)

Gain Recognized

$$ \text{Gain Recognized} = \min(\text{Realized Gain}, \; \text{Unreinvested Proceeds}) $$

Replacement Property Basis

$$ \text{Basis in Replacement Property} = \text{Cost of Replacement Property} - \text{Deferred Nonrecognized Gain} $$
  • Replacement Windows: 2 years from year-end for casualty/theft; 3 years from year-end for condemned trade/business/investment real property.
  • Gain Recognition: Gain is recognized only to the extent insurance/condemnation proceeds are not reinvested in qualified replacement property.

Divorce Property Settlements (§1041)

  • Transfers between spouses incident to divorce are 100% tax-free (no gain or loss recognized).
  • Recipient spouse takes the transferor's carryover adjusted basis and holding period.

Corporate Treasury Stock (§1032)

  • Corporations recognize zero gain or loss on sales, repurchases, exchanges, or reissuances of their own capital stock.

Specific Asset Dispositions

Small Business Stock: Section 1244 Loss vs. Section 1202 QSBS

Attribute Section 1244 (Downside Loss Planning) Section 1202 QSBS (Upside Gain Planning)
Primary Tax Benefit Converts capital loss on disposition or worthlessness into an Ordinary Loss. Excludes gross gain on disposition of qualified stock:
  • 100% Exclusion for stock acquired on or before July 4, 2025 (after Sept. 27, 2010).
  • Tiered Exclusion for stock acquired after July 4, 2025:
    • 50% (held > 3 years)
    • 75% (held > 4 years)
    • 100% (held > 5 years)
Eligible Taxpayers Original individual shareholders or original partners of partnerships holding the stock directly from issuance. Noncorporate investors (individuals, eligible trusts, estates, and pass-through partners).
Corporate Size Limitation Aggregate money and property received for stock, paid-in capital, and contributions to capital must not exceed $1,000,000 at the time stock is issued. Aggregate gross assets must not exceed:
  • $50,000,000 for stock issued on or before July 4, 2025.
  • $75,000,000 for stock issued after July 4, 2025 (indexed for inflation post-2026).
(Tested at all times before and immediately after issuance).
Holding Period Requirement No minimum holding period required.
  • Stock acquired ≤ July 4, 2025: More than 5 years.
  • Stock acquired after July 4, 2025: More than 3 years for partial exclusion; more than 5 years for full exclusion.
Annual / Lifetime Limits Maximum ordinary loss per year:
  • $50,000 for Single / Married Filing Separately
  • $100,000 for Married Filing Jointly
(Any excess loss is characterized as capital loss).
Cumulative gain exclusion per issuer is capped at the greater of:
  • 10 × Taxpayer's Adjusted Basis of stock sold in the tax year, OR
  • Dollar Cap:
    • $10,000,000 ($5,000,000 for MFS) for stock acquired ≤ July 4, 2025
    • $15,000,000 ($7,500,000 for MFS; indexed for inflation post-2026) for stock acquired after July 4, 2025

Installment Sale Formulas

Gross Profit

$$ \text{Gross Profit} = \text{Selling Price} - \text{Adjusted Basis} - \text{Selling Expenses} - \text{Ordinary Depreciation Recapture} $$

Total Contract Price

$$ \text{Contract Price} = \text{Selling Price} - \min(\text{Qualifying Debt Assumed}, \, \text{Installment Basis}) $$

Gross Profit Percentage (GPP)

$$ \text{Gross Profit Percentage (GPP)} = \frac{\text{Gross Profit}}{\text{Contract Price}} $$

Current Year Taxable Gain

$$ \text{CY Taxable Gain} = \Big(\text{Principal Received} + \max(0, \, \text{Debt Assumed} - \text{Installment Basis})\Big) \times \text{GPP} $$

Recapture & Character Ordering Rules

Ordinary Recapture (§ 1245 & § 1250 excess): Must be recognized fully as ordinary income in the year of sale under IRC § 453(i), regardless of cash received, and is added back to basis for installment calculations.

Unrecaptured § 1250 Gain (Real Estate Straight-Line): Remains eligible for installment deferral under Treas. Reg. § 1.453-12, but must be recognized first out of principal payments received (taxed up to 25%) before any remaining gain is characterized as general long-term capital gain.

Related Party Transactions

Includes family (siblings, spouses, ancestors, lineal descendants), >50% owned entities, and controlled groups.

Disallowed Losses

Losses on sales between related parties are permanently disallowed for the seller. However, the buyer can use the disallowed loss to offset a gain on a future sale to an unrelated party.

Subsequent Sale to Unrelated Party

When the buyer eventually sells the property to an unrelated party, the recognized gain or loss depends on the new sales price relative to the original relative's cost basis:

graph TD Start["Subsequent Sale Price"] --> Q1{"Compare to Original Cost & Purchase Price"} Q1 -->|"> Original Relative's Cost Basis"| Gain["Recognize GAIN
(Basis = Original Relative's Cost)"] Q1 -->|"< Related-Party Purchase Price"| Loss["Recognize LOSS
(Basis = Purchase Price)"] Q1 -->|"Between Cost & Purchase Price"| NoGL["No Gain or Loss Recognized"]

Constructive Ownership Rules

  1. Stock owned by a corp/partnership/trust is treated as owned proportionately by its shareholders/ partners/beneficiaries.
  2. An individual is considered to own the stock of their family members.

Related-Party Depreciable Property & Constructive Ownership Attribution

  • Section 1239 Depreciable Property Rule: If property that is depreciable in the hands of the buyer is sold between related persons (e.g., an individual and their > 50% owned entity), 100% of recognized gain is recharacterized as ORDINARY INCOME.
  • Family Attribution Limitation: Stock constructively owned through an entity (Rule 1) can be re-attributed. However, stock constructively owned through a family member (Rule 2) CANNOT be re-attributed to another family member.

Trusts, Estates & Tax-Exempt Entities

Trusts & Estates: Income Taxation

Estates and trusts are separate income-tax-paying entities. Income is taxed at either the entity level (if retained) or the beneficiary level (if distributed), but not both.

Trust Classifications

Trust Type Exemption Key Characteristics
Simple Trust $300 Must distribute all income currently. Cannot make charitable contributions. Cannot distribute principal (corpus).
Complex Trust $100 Any trust not classified as simple. May accumulate income, make charitable contributions, and distribute principal.
Grantor Trust N/A Grantor retains control. Disregarded as a separate tax entity; all income/deductions flow directly to the grantor's Form 1040.
Revocable Trust N/A A specific type of grantor trust where the creator reserves the right to alter or terminate. Becomes an irrevocable trust upon death.

Distributable Net Income (DNI)

DNI establishes the maximum amount of income taxed to beneficiaries and deducted by the trust. It also determines the character of the income (e.g., tax-exempt).

$$ \begin{aligned} &\text{Estate/Trust Taxable Income (before distribution deduction)} \\ + \; &\text{Personal Exemption} \\ - \; &\text{Capital Gains (allocated to corpus)} \\ + \; &\text{Capital Losses (if allocated to corpus)} \\ + \; &\underline{\text{Tax-Exempt Interest (net of related expenses)}} \\ = \; &\textbf{Distributable Net Income (DNI)} \end{aligned} $$

Trust Accounting Income (TAI) vs. Distributable Net Income (DNI)

Concept Trust Accounting Income (TAI) Distributable Net Income (DNI)
Governing Standard Trust document and state Uniform Fiduciary Income and Principal Act. Internal Revenue Code tax calculation.
Allocation of Receipts
  • Income Allocation: Dividends, interest, net rental receipts.
  • Principal / Corpus: Capital gains, stock splits, insurance proceeds.
CEILING on taxable income reportable by beneficiaries and maximum deduction for Form 1041.
Fiduciary Fees Typically allocated 50% to Income and 50% to Principal. Deductible administration expenses reduce taxable income in calculating DNI.

Fiduciary Income Distribution Deduction & The 65-Day Rule

$$ \text{Income Distribution Deduction} = \min\Big(\text{Actual TAI Distributed}, \; \text{DNI} - \text{Net Tax-Exempt Interest}\Big) $$
  • Personal Exemptions: Simple Trust = $300; Complex Trust = $100; Estate = $600.
  • 65-Day Rule: Fiduciary can elect to treat distributions made within the first 65 days of the subsequent tax year as having been paid on the final day of the prior tax year.

Tax-Exempt Organizations

Obtaining & Maintaining Tax-Exempt Status (Section 501(c)(3))

Organizations operated exclusively for religious, charitable, scientific, testing for public safety, literary, or educational purposes. To maintain status:

  • No part of net earnings may benefit private interests/shareholders.
  • Substantial part of activities cannot be attempting to influence legislation (lobbying limits).
  • May not directly or indirectly participate or intervene in any political campaign on behalf of (or in opposition to) any candidate for public office.

Unrelated Business Income (UBI)

Income from a trade or business that is regularly carried on and not substantially related to the organization's tax-exempt purpose. Subject to Unrelated Business Income Tax (UBIT) at corporate rates.

  • Statutory Exclusions from UBI (Not Subject to UBIT):
    • Passive Investment Income: Dividends, interest, annuities, and royalties.
    • Real Property Rents: Unleveraged rental income from real property (rents based on net profits are taxable).
    • Property Dispositions: Capital gains and losses from sales of non-inventory investment property.
    • Research Activities: Income derived from research conducted for government entities, colleges, or hospitals.
    • Volunteer-Run Activities: Businesses where substantially all work is performed without compensation (e.g., volunteer bake sales).
    • Member Convenience Activities: Operations conducted primarily for the convenience of members, students, or employees (e.g., university cafeterias, hospital gift shops).
    • Donated Merchandise Sales: Sale of donated items (e.g., thrift shops).
    • Qualified Entertainment: Qualified bingo games, public entertainment, conventions, and trade show activities.