Tag Archives: tax planning

2025 Year-End Tax Planning for Traders and Investors Under the OBBBA

October 29, 2025 | By: Robert A. Green, CPA

Join Robert A. Green, CPA, for our annual year-end tax planning webinar tailored for active traders and investors. The 2025 One Big Beautiful Bill Act (OBBBA) made major TCJA provisions permanent, creating new opportunities for traders to lock in lower tax rates and expanded deductions. This session will cover how to optimize your tax outcome before December 31—by managing Trader Tax Status (TTS), Section 475 elections, S-Corp wages, PTET payments, and retirement plans. Learn practical strategies to coordinate income, deductions, and entity-level benefits to maximize your 2025 savings and prepare for 2026. Perfect for individual traders, fund managers, and tax professionals who advise active traders.

If you can’t join us live, register, and you will automatically receive a link to the recording after the session ends. You don’t have to be a client of IBKR.

2025 Year-End Tax Planning for Traders and Investors Under the OBBBA

October 8, 2025 | By: Robert A. Green, CPA | Read it on

Get ready for year-end with proactive tax planning for traders. The One Big Beautiful Bill Act (OBBBA) made many TCJA provisions permanent and extended valuable deductions for traders. Smart timing of income, PTET payments, and S-Corp benefits before December 31 can lower your 2025 tax bill and set you up for success in 2026.


Overview Introductory Note on Financial Product Tax Treatment

Every trader should understand how different financial instruments are taxed. Securities, futures, options, ETFs, ETNs, forex, digital assets, precious metals, and commodities are all subject to different tax treatments. This post includes a complete reference section later in the article detailing those distinctions.


Overview

Year-end is the best time for active traders to take control of their 2025 tax outcome. With significant changes under the One Big Beautiful Bill Act (OBBBA), signed July 4, 2025, traders can capitalize on lower tax rates, wider brackets, and enhanced deductions made permanent from the 2017 Tax Cuts and Jobs Act (TCJA). Whether you’re using Trader Tax Status (TTS), the Section 475 mark-to-market (MTM) election, or traditional capital-gain treatment, proactive steps before December 31 can save thousands in taxes.


1. OBBBA Made TCJA Benefits Permanent

Note: 2025 thresholds verified under OBBBA; cross‑checked with multiple trusted tax publishers to ensure accuracy, as IRS pages may remain outdated.

  • Lower tax brackets preserved: The top individual rate remains 37%, avoiding the scheduled rise to 39.6%. Marriage penalty relief is available across most brackets.

  • Higher standard deduction: $15,750 single / MFS, $31,500 MFJ, and $23,625 HOH for 2025 (filed in 2026).

  • Qualified Business Income (QBI) deduction retained: Section 199A continues for traders with TTS and Section 475 income, subject to thresholds.

  • $40,000 SALT deduction cap: Extended for 2025 (with 1% annual indexing through 2029).

  • 100% bonus depreciation: Permanently reinstated for qualifying assets placed in service after January 19, 2025.

  • Section 174A – Internal-Use Software Expensing: Domestic R&E expenses, including internal-use software, are fully deductible in the year incurred.

These provisions give traders and their pass-through entities a stable planning framework for years ahead.


2. The SALT Cap and PTET Strategy Still Matter

The $40,000 SALT cap doesn’t eliminate the advantage of Pass-Through Entity Tax (PTET) elections. PTET allows partnerships and S-corps to pay state tax at the entity level, making it fully deductible against business income for federal purposes—bypassing the SALT cap.

Action items:

  • Confirm or elect PTET before your state’s deadline.

  • Pay 2025 PTET installments by year-end to secure the deduction.

  • Coordinate your PTET with your QBI deduction and NIIT exposure to maximize overall benefit.


3. Capital Gains and Loss Harvesting Still Work

“Selling losers to offset winners” remains a core year-end move.

For active traders without Sections 475 or 1256 (futures):

  • Harvest losses to offset realized capital gains.

  • Use up to $3,000 of net capital loss to offset ordinary income.

  • Match long-term losses against short-term gains—taxed up to 37% plus 3.8% NIIT.

For Section 475 securities traders, wash-sale and capital-loss limitations are eliminated; ordinary losses can now offset all sources of income.

Investors must still comply with wash-sale rules under Section 1091, which disallow losses when substantially identical securities are repurchased within 30 days before or after the sale.


4. Avoid the Wash-Sale Trap

Under Section 1091, no loss is recognized if you reacquire substantially identical stock or securities within 30 days before or after the date of sale. This can occur across multiple brokerages or even IRAs. (IRA accounts on their own do not have wash sales.)

Warning: It’s a problem when you repurchase a losing trade from a taxable account in an IRA. That causes a permanent loss of the wash sale, whereas in taxable accounts, wash sales are merely deferred. 

The IRS wash sale rules for brokerage firms are narrower and differ from the IRS rules for taxpayers, which are broader. Brokers report wash sales for each account based on identical securities. Conversely, taxpayers should report wash sales on all accounts on a combined basis, as well as on substantially identical securities. For year-end planning, consider using TradeLog to comply with the IRS wash sale rules for taxpayers. 

Trader tips:

  • Close losing positions by mid-December to ensure 2025 loss recognition, and wait for the rest of the 30 days in January 2026 before repurchasing a substantially identical security. (“Break the chain” strategy.)

  • Turn off DRIPs before year-end.

  • Replace exposure with similar but not identical ETFs (e.g., sell SPY, buy SPLG). Each ETF has S&P 500 exposure, but they are not substantially identical. 

  • Section 475 traders are exempt from wash sales.


5. Timing Income and Deductions Under OBBBA

  • Defer income to 2026 if possible—through timing of C-corp dividends, bonuses, or realized gains. (Partnership and S-corp distributions are generally non-taxable and don’t defer income.)

  • Accelerate losses and deductions into 2025 if you expect income to drop in 2026, capturing current-year savings while rates remain constant.

  • Bunch charitable or state-tax payments to exceed the higher standard deduction in alternating years, and itemize deductions. (The new above-the-line charitable deduction doesn’t apply until the 2026 tax returns.)


6. Section 475 and Trader Tax Status: Positioning for 2025 and Beyond

Although the Section 475(f) election for 2026 is filed with your 2025 return or extension (April 15, 2026, for individuals, March 15, 2026, for partnerships/S-corps), Q4 2025 is the time to evaluate your Trader Tax Status (TTS) and decide how Section 475 fits into your broader plan.

Consider using Green’s Trader Tax Status Qualification App

Why This Matters at Year-End

  • Under 475, all trading gains and losses become ordinary, eliminating the $3,000 capital-loss limit and wash-sale deferrals.

  • Staying under capital-gain treatment allows for loss harvesting and preferential long-term rates.

  • Once elected, 475 applies only while TTS is active; if TTS lapses, the mark-to-market method is suspended for the non-TTS period.

Assessing TTS Eligibility Before Year-End

TTS qualification determines whether you can deduct trading business expenses and apply Section 475 for 2025 (if you previously elected Section 475 on time).
If you cease active trading before year-end—for example, TTS stops after Q3—then Section 475 is suspended for Q4 2025, and trading after that point reverts to capital-gain treatment.

Maintain a consistent trading cadence through Q4 to preserve TTS for the entire year and keep Section 475 in effect without interruption.

If a trader wants to form a new entity for TTS and tax benefits, they should have created it before the start of Q4. Establishing an entity for only one quarter of the year is generally not enough time to safely demonstrate TTS eligibility or fully utilize related deductions and benefits.

Segregating Investments From Trading

Traders eligible for TTS and using Section 475 can also maintain separate investment positions, subject to capital gains taxation. To preserve this distinction and comply with IRS rules:

  • Use separate brokerage accounts for 475(f) trading vs. investments.

  • Avoid holding the same or substantially identical securities in both accounts.

  • If investments are held inside a 475 account, you must contemporaneously record each investment in your records on the day of purchase (e.g., in a trade log or journal). Without this same-day identification, the IRS may treat the position as a 475 trading position or bar a loss from using the 475 method.

  • Do not reclassify losing investments as trading positions later—a TTS trader cannot convert a losing investment position into a trading position to turn an unrealized capital loss into an ordinary loss. Such retroactive relabeling violates Section 475 and can trigger IRS adjustments and penalties.

  • Maintain documentation that demonstrates investment intent, more extended holding periods, and a reduced frequency of trading.

  • Report trading under Form 4797 and investments on Form 8949 / Schedule D.

This segregation ensures you retain the benefits of both worlds—ordinary-loss treatment for trading (and QBI deduction on Section 475 income), and preferential capital-gains rates for long-term investments.

Accelerating Expenses Under OBBBA

If TTS is strong in 2025 but uncertain for 2026, consider accelerating business expenses into 2025 to secure full deductions while TTS clearly applies. The One Big Beautiful Bill Act (OBBBA) strengthened TCJA’s bonus depreciation rules, allowing 100% expensing for most business equipment, computers, furniture, and software placed in service by December 31, 2025.

Other acceleration opportunities:

  • Prepay subscriptions, education, and trading-related services within the 12-month rule.

  • Upgrade trading workstations and technology before year-end to qualify for full expensing.

  • Pay professional and advisory fees (such as tax consultations or accounting software) by December 31 for the 2025 deduction.


7. The QBI Deduction: Preserve It With an S-Corp

The Section 199A Qualified Business Income (QBI) deduction continues after OBBBA and remains a valuable planning opportunity for traders with TTS who use the Section 475(f) method. The deduction equals up to 20% of qualified ordinary trading income, minus TTS expenses, and can lower the effective top rate from 37% to about 29.6% when applicable.

Phaseout thresholds (2025): The OBBBA made the Section 199A QBI deduction permanent but left 2025 thresholds unchanged. For tax year 2025, the existing SSTB limits remain in effect: $197,300 (single and other) and $394,600 (MFJ), with phaseouts ending at $247,300 and $494,600, respectively. Beginning in 2026, the OBBBA significantly expands these ranges, increasing the phaseout window from $50,000 to $75,000 for single filers and from $100,000 to $150,000 for joint filers. The income thresholds themselves will adjust for inflation in 2026. The law also introduces a new minimum QBI deduction of $400 for taxpayers with at least $1,000 of QBI from an active business, indexed for inflation starting in 2027.

Understanding QBI Mechanics for Traders

  • Within the phaseout range, an SSTB like a TTS trading business may qualify for a partial deduction based on the lesser of:

    • 20% of qualified business income (QBI), or

    • The greater of 50% of W-2 wages, or 25% of W-2 wages plus 2.5% of the unadjusted basis (UBIA) of qualified property.

  • Traders generally have little or no qualified property, so the 50% of W-2 wages test typically applies.

  • A TTS S-Corp can pay the owner W-2 wages, unlocking health insurance and retirement plan deductions, as well as potentially supporting a limited QBI deduction within the phaseout range.

  • Partnerships and sole proprietorships cannot pay the owner W-2 wages; however, they can include non-owner employee wages to satisfy the wage limitation test.

Planning Notes

Because trading is an SSTB, the QBI deduction phases out entirely once taxable income exceeds the upper threshold. For traders with taxable income inside the phaseout range, S-Corp wages can help optimize QBI benefits while preserving access to health insurance and retirement deductions.


8. Retirement and S-Corp-Level Planning

TTS S-Corp entities offer valuable benefits, including Solo 401(k) and SEP IRA contributions, as well as health insurance deductions. Make elective deferrals by December 31 and employer contributions by the filing deadline. Ensure S-corp payroll meets the wage base for both retirement limits and QBI optimization.

2025 Retirement Contribution Limits 

  • Solo 401(k) elective deferral: $23,500 (employee contribution limit)

  • Catch-up contribution (age 50+): $7,500

  • SECURE 2.0 catch-up (ages 60–63): $11,250 (if plan allows)

  • Employer profit-sharing contribution: Up to 25% of W-2 wages, capped at $46,500.

  • Total contribution limit: $70,000 ($77,500 including catch-up)

S-Corp Advantage for Traders

  • Earned income: S-Corp officer compensation qualifies as earned income, allowing for deductions for health insurance and retirement plans.

  • Solo 401(k) deadlines: The plan must be established by December 31, 2025, with elective deferrals made by the end of the year. Employer contributions (profit sharing) are deductible through the S-Corp return due date, including extensions (generally September 15, 2026).

  • SEP IRA option: Simplified alternative; 25% of compensation up to the same annual limits. No elective deferrals or catch-ups. The Solo 401(k) requires less salary, resulting in savings on payroll taxes. 

  • No “reasonable compensation” rule: A TTS S-Corp determines wages based on desired health insurance and retirement benefits, as well as QBI deductions in the phaseout range, rather than on general industry standards or the 25% to 50% of net income norm.

For more details, see GreenTraderTax Retirement Solutions.


9. New OBBBA Temporary Provisions Affecting Individuals

Temporary for tax years 2025 through 2028. For non-itemizers and itemizers.

  • Senior Deduction $6,000/year single, $12,000 MFJ. Age 65 or older. Phases out (MAGI) over $75,000 single or $150,000 MFJ.
  • Overtime Deduction capped at $12,500/ year single, $25,000 MFJ. Phases out (MAGI) over $150,000 single, or $300,000 MFJ.
  • Car-Loan Interest Deduction up to $10,000. Phases out (MAGI) over $100,000 single, or $200,000 MFJ.

Other OBBBA provisions are permanent.

  • Permanent 60% AGI limit for cash charitable gifts.

  • Estate & Gift exemption rises to $15 million in 2026—update estate plans.

  • Pease Limitation repealed—itemized deductions less restricted for high earners.


10. Year-End Example: Active Trader Couple

Scenario: Married TTS traders using an S-Corp, filing jointly

  • $550K Section 475 income (ordinary)

  • $50K long-term capital gains

  • $20K unrealized losses

Moves before December 31:

  1. Elect PTET for S-Corp → $35K state tax deduction from gross income, unlocking full standard deduction on individual tax return.

  2. Harvest (sell) $20K capital losses → offset against capital gains.

  3. Contribute the maximum allowed $70K Solo 401(k) through S-Corp.

  4. Health insurance deduction $25k through S-Corp.

  5. Pay $186K W-2 salary → to maximize Solo 401(k) and also qualify for partial QBI deduction within the phaseout range.

  6. Donate $10K cash → within 60% AGI limit. (Use standard deduction, which is higher)

Calculations:

  • Gross income = $580K (550k trading + 30k LTCG).

  • Deduct 130k = PTET ($35K) from gross income, Solo 401(k) ($70K) AGI deduction, ($25k) health insurance AGI deduction, Adjusted gross income = $450K.

  • Standard deduction ($31.5K) → taxable income ≈ $418.5K.

  • This keeps taxable income within the QBI phaseout range (starts $394.6K, ends $494.6K MFJ for 2025), allowing a partial QBI deduction.

Result: Taxable income reduced by ~$130K, enabling a limited QBI deduction, NIIT savings, and lower effective tax rate — demonstrating coordination of PTET, retirement, health, and capital loss harvesting. Payroll is the lever that counts, so find your sweet spot to unlock the most tax savings.  


11. Final Checklist for December 31

  • Review YTD trading and investment gains/losses

  • Harvest capital losses and avoid wash-sales

  • Maximize state PTET through S-Corps and LLC/partnerships

  • Maximize health insurance and retirement contributions through an S-Corp

  • Execute S-corp payroll before the year-end

  • Confirm TTS status through year-end

  • Accelerate TTS expenses (100% expensing)

  • Schedule 2025 tax consultation


12. Tax Treatment of Financial Products: Detailed Reference

Every trader should understand how different financial instruments are taxed. Below is an expanded summary organized by the categories in the GreenTraderTax Tax Treatment Center and the “Explore Tax Treatment on Financial Products” section:

Capital Loss Carryovers: Capital losses offset capital gains and up to $3,000 of ordinary income ($1,500 if married filing separately). Unused losses carry forward indefinitely. Section 475(f) traders report ordinary losses that do not absorb capital-loss carryovers.

Securities: Stocks and narrow-based ETFs are subject to realization accounting, capital gains treatment, and wash-sale loss deferrals under Section 1091. Traders qualifying for TTS can elect Section 475(f) treatment for ordinary gain or loss, thereby avoiding wash sales and the $3,000 limitation. Report on Form 8949/Schedule D or Form 4797 if using Section 475.

Section 1256 Contracts (Futures, Broad-Based Index Options): Receive 60% long-term and 40% short-term capital gains treatment, regardless of holding period. Section 1256 contracts are marked-to-market at year-end, and losses may be carried back three years against prior Section 1256 gains (as reported on Form 6781). Traders can also opt for a mixed straddle treatment.

Options: Equity options are taxed as securities. Gains or losses are capital and depend on the holding period. Wash-sale rules apply to substantially identical options. Complex rules for straddles, constructive sales, and Section 1258 conversion transactions can defer losses or recharacterize gains. Options on futures are taxed the same as futures, which are Section 1256 contracts.

Exchange-Traded Funds (ETFs): Most ETFs are registered investment companies (RICs) taxed as securities. Commodity or futures-based ETFs may issue K-1s with Section 1256 gains, but for sales, they are treated like securities. Grantor-trust metals ETFs (e.g., GLD, SLV) are taxed as collectibles (28% maximum rate).

Forex: Spot and forward contracts default to Section 988 ordinary gain or loss treatment. Traders can elect out of Section 988 for specific contracts and into Section 1256(g) for capital-gains treatment, but elections must be made prospectively.

Cryptocurrencies and Digital Assets: See Digital Asset Trading Explained: Tax Rules for Crypto ETFs, Futures, Options, and Tokens. Digital assets are treated as property for federal tax purposes, rather than as currency. Traders must report sales and exchanges as capital transactions. Short-term and long-term capital gains apply based on the holding period. Mining, staking, and airdrops generate ordinary income at the time of receipt. Crypto futures on regulated U.S. exchanges qualify as Section 1256 contracts (60% long-term / 40% short-term). Wash-sale rules currently do not apply to crypto but may under future legislation. ETFs and ETNs holding digital assets follow their fund structure—RIC, grantor trust, or partnership. Proper recordkeeping is essential: use software or blockchain explorers to track cost basis, proceeds, and holding periods accurately.

Other Financial Products: This includes swaps, structured notes, CFDs, and foreign exchange derivatives. Most are subject to ordinary income treatment unless they qualify for capital gains under specific elections. See Other Instruments for detailed character and timing rules.

Volatility exchange-traded notes (ETN) are structured as “prepaid forward contracts” or “debt instruments.” The IRS does not consider an ETN prepaid forward contract a security, whereas ETN debt instruments are. Sales of ETN prepaid forward contracts use the capital gains realization method on sales. Because it’s not a security, ETN prepaid forward contracts (i.e., VXX) are not subject to wash-sale loss adjustments or Section 475 (if elected).

Short Selling: Short sales are not recognized until the position is closed. Gains are always short-term. Losses are also short-term, except in rare cases involving hedging or straddling. Shorting substantially identical securities may create constructive sales or defer losses.


13–26. Expanded Planning Topics

13. Excess Business Loss & NOL: $313k single / $626k MFJ 2025 thresholds; excess business losses (EBL) become NOL carryforwards with an 80% income offset limit in the subsequent years. (The 2026 amount is $256k single / $512k MFJ after changes from OBBBA. The 2026 limits are lower than for the 2025 tax year. That gap reflects a smaller COLA/inflation adjustment in 2026 than in 2025. OBBBA reset the baseline for EBL inflation indexing to the pre‑2017 period.)

14. Defer vs. Accelerate: Match timing to expected 2026 income shifts.

15. Roth IRA conversions: Pair with Section 475 losses to use brackets efficiently.

16. 0% LTCG: 2025 thresholds $48,350 single / $96,700 MFJ / $64,750 HOH.

17. NIIT: 3.8% surtax above $200k single / $250k MFJ / $125k MFS.

18. Business expenses: 100% expensing; $2,500 de minimis; investment expense suspension continues.

19. Estimated taxes: Pay Q4 by January 15, 2026; consider adding to withholding at year-end to avoid underestimated tax penalties. Consider paying state estimated taxes before December 31, 2025, to take advantage of the new $40k SALT cap. However, keep an eye on AMT for which SALT is not deductible.

20. Wash-sale tactics: Use a new 2026 entity to reset positions, which breaks the chain on 2025 wash-sale losses.

21. TTS & Section 475 ops: Timely elections; mid-year suspension planning. If you have a significant capital loss carryover going into 2026, consider the pros and cons of making a 475 election. See chapter 2 of Green’s 2025 (or 2026) Trader Tax Guide for decision-making rationale.

22. S-Corp benefits: W-2 pay, accountable plans, health & Solo 401(k) integration, PTET SALT cap workaround, and QBI phaseout ranges.

23. New entity setup for 2026: Form single-member LLC in Dec 2025. On January 1, 2026, add your spouse as a partner in a partnership or elect S-Corp treatment for 2026. Elect Section 475 within 75 days of inception (January 1, 2026) by internal resolution for the LLC/partnership or S-Corp. “new taxpayer” exception.

24. Straddles: Avoid constructive sale/receipt traps.

25. Charitable: Donate appreciated stock; 60% AGI limit.

26. Disaster relief: Monitor IRS/state relief, including extended payments and tax returns, plus tax loss benefits. 


Conclusion

OBBBA locks in a favorable tax environment for traders—but timing, TTS qualification, entity strategy, and QBI management still separate the merely compliant from the truly optimized. Before December 31, review your positions, confirm elections, and fine-tune income levels to maximize deductions and minimize your tax liability.

Schedule Your 2025 Trader Tax Planning Consultation
The GreenTraderTax team at Green, Neuschwander & Manning, LLC, can help you navigate these changes and tailor a strategy for your trading business.
Book Now → greentradertax.com/services/consultations

Tips For Traders On Preparing 2024 Tax Returns

January 7, 2025 | By: Robert A. Green, CPA

Join Darren Neuschwander, CPA, managing member of Green, Neuschwander & Manning, LLC, for insights and information to help traders file their 2024 federal tax returns. This session will go over how active traders can qualify for trader tax status (TTS) to deduct business, start-up, and home office expenses on 2024 tax returns. Active securities traders trigger many wash sale loss adjustments, which can defer capital losses to the subsequent year. TTS traders can elect Section 475 mark-to-market accounting on securities, which exempts them from wash sale losses and the $3,000 capital loss limitation. It’s ordinary income or loss. However, the 2024 Section 475 election was due by April 15, 2024. 

 

 

Year-End Tax Planning For Traders

October 28, 2024 | By: Robert A. Green, CPA

Join Robert A. Green, CPA, of GreenTraderTax.com in his webinar on year-end tax planning for traders. Don’t wait until April 2025; arrange tax savings for 2024 before the year-end. Learn about tax-loss selling, avoiding wash sale losses, paying estimated taxes, and other tax-saving strategies. 

Year-End Tax Planning For Traders

September 26, 2024 | By: Robert A. Green, CPA

Presentation slides

Join Robert Green, CPA of GreenTraderTax.com, and Darren Neuschwander, CPA of Green, Neuschwander & Manning, LLC, in their webinar on year-end tax planning for traders. Don’t wait until tax time in April; arrange tax savings before year-end. Learn about deferring income, accelerating deductions, tax-loss selling, avoiding wash sale losses, paying estimated taxes, S-Corp payroll with health and retirement benefits, SALT cap workaround strategies for pass-through entities, and other tax-saving strategies. Green and Neuschwander will cover recent changes in tax law that affect traders.

If you can’t join us live, register, and you will automatically receive a link to the recording after the session ends. You don’t have to be a client of IBKR.

Significant Tax Moves For Traders To Make in Q1 2024

January 2, 2024 | By: Robert A. Green, CPA

Slide presentation

Join Robert A. Green, CPA, from GreenTraderTax.com, for insights and information to help traders.

  • Green will interview Darren Neuschwander, CPA, of Green, Neuschwander & Manning, LLC. Mr. Neuschwander will give tips on how to get organized early to improve tax season results.
  • Fourth quarter estimated taxes are due Jan. 16, 2024. Learn to avoid a 7 to 8% underestimated tax penalty.
  • Do not trigger 2023 wash sale losses by repurchasing losing trades in January 2024.
  • Focus on extensions due April 15, 2024, for individuals and March 15, 2024, for partnerships and S-Corps.
  • Learn how to assess qualification for trader tax status (TTS) in 2023 and 2024.
  • TTS traders should consider a Section 475 MTM election with a federal extension.
  • Focus on trade accounting for various tax treatments for securities, futures, options, ETFs, ETNs, and cryptocurrencies.
  • Learn how to read a broker-issued Form 1099-B.

If you can’t join us live, register, and you will automatically receive a link to the recording after the session ends. You don’t have to be a client of IBKR.

Year-End Tax Planning For Traders

October 24, 2023 | By: Robert A. Green, CPA

Presentation Slides

Join Robert A. Green, CPA of GreenTraderTax.com, in his webinar on year-end tax planning for traders. Don’t wait until tax time in April 2024; arrange tax savings for 2023 before the year-end. Learn about tax-loss selling, avoiding wash sale losses, paying estimated taxes, and other tax-saving strategies.

Tax Planning For S-Corps

September 22, 2023 | By: Robert A. Green, CPA

Read our related blog post and watch the webinar, Tax Planning For Traders.

Traders eligible for trader tax status (TTS) use an S-Corp to unlock health, retirement, and SALT deductions. It’s important to act before year-end using payroll. 

S-CORP OFFICER COMPENSATION

TTS traders use an S-Corp to arrange health insurance and retirement plan deductions. These deductions require earned income or self-employment income. Unlike trading gains, which are unearned income, a TTS S-Corp salary is earned income.

S-Corps pay officer compensation in conjunction with employee benefit deductions through payroll tax compliance done before year-end 2023. Otherwise, traders miss the boat. TTS is necessary since an S-Corp investment company cannot have tax-deductible wages, health insurance, or retirement plan contributions. A trading S-Corp is not required to have “reasonable compensation,” so a TTS trader may determine officer compensation based on how much to reimburse for health insurance and how much they want to contribute to a retirement plan. Remember, sole proprietor and partnership TTS traders cannot pay salaries to 2% or more owners; hence, the S-Corp is needed.

S-Corp wages impact the SALT cap workaround, hinges on net income after wages. If you fall into the QBI phase-out range, wages are required to increase the QBI deduction. This decision-making has many moving levers, so consult your CPA for year-end tax planning in early December.

S-CORP HEALTH INSURANCE

S-Corps may only deduct health insurance for the months it was operational and qualified for TTS. Employer-provided health insurance, including Cobra, is not deductible.

The S-Corp reimburses the employee/owner through the accountable reimbursement plan before the end of the year. Add the health insurance reimbursement to taxable wages, but do not withhold social security or Medicare taxes from that portion of W-2 compensation. The officer/owner takes an AGI deduction for health insurance on their tax return.

A taxpayer can deduct a contribution to a health savings account (HSA) without TTS or earned income.

S-CORP RETIREMENT PLAN CONTRIBUTION

TTS S-Corps can unlock a retirement plan deduction by paying sufficient officer compensation in December 2023 when results for the year are evident. Net income after deducting wages and retirement contributions should be positive.

If you want to, you must establish a Solo 401(k) retirement plan for a TTS S-Corp with a financial intermediary before the year’s end. Plan to pay the 100%-deductible “elective deferral” amount up to a 2023 maximum of $22,500 (or $30,000 if age 50 or older with the $7,500 catch-up provision) with the December 2023 payroll. That elective deferral is due by the end of January 2024. You can fund the 25% profit-sharing plan (PSP) portion of the S-Corp Solo 401(k) up to a maximum of $43,500 by the 2023 S-Corp tax return due date, including an extension, which means September 15, 2024. The maximum PSP contribution requires wages of $174,000 ($43,500 divided by a 25% defined contribution rate). The maximum contribution for those under age 50 is $66,000 for 2023. For those 50 or older, it’s $73,500 for 2023. Tax planning calculations will show the projected outcome of the various options of income tax savings vs. payroll tax costs.

Consider a Solo 401(k) Roth for the elective-deferral portion only, where the contribution is not deductible, but the contribution and growth within the Roth are permanently tax-free. Traditional plans have a tax deduction upfront, and all distributions are subject to ordinary income taxes in retirement.

Traditional retirement plans have required minimum distributions (RMD) by age 73 in 2023, whereas Roth plans don’t have RMD. (See SECURE Act 2.0 RMD rules at https://www.irs.gov/retirement-plans/retirement-plan-and-ira-required-minimum-distributions-faqs.)

SALT CAP

TCJA capped state and local income, sales, and property taxes (SALT) at $10,000 per year ($5,000 for married filing separately) and did not index it for inflation. About 29 states enacted SALT cap workaround laws. Search “(Your state) SALT cap workaround” to learn the details for your state. Most states follow a blueprint approved by the IRS.

Generally, elect to make a “pass-through entity” (PTE) payment on a partnership or S-Corp tax return filed by your business. It doesn’t work with a sole proprietorship filing a Schedule C. PTE is a business expense deduction shown on the state K-1 like a withholding credit. Most states credit the individual’s state income tax liability with the PTE amount. Essentially, you convert a non-deductible SALT itemized deduction (over the cap) into a business expense deduction from gross income. Act well before year-end; otherwise, you might delay the benefit to next year.

HAVE YOUR NEW ENTITY READY ON JAN. 1, 2024

If you missed employee benefits (health insurance and retirement contributions) in 2023, consider an LLC with an S-Corp election for the tax year 2024. Or you may want a spousal-member LLC taxed as a partnership for 2024 to maximize the SALT cap workaround and segregate trading from investing.

If you want the new entity to be ready to trade on the first trading day of January 2024, consider the following plan. Form a single-member LLC in December 2023, obtain the employee identification number (EIN) online, and open the LLC brokerage account before year-end to be ready to trade as of Jan. 1, 2024. The single-member LLC is a “disregarded entity” for the tax year 2023, which avoids an entity tax return filing for the initial short year 2023. You can add your spouse as an LLC member on Jan. 1, 2024, creating a partnership tax return for 2024. 

If you want health insurance and retirement plan deductions for 2024, then your single-member or spousal-member LLC should submit a 2024 S-Corp election within 75 days of Jan. 1, 2024.

The partnership or S-Corp is a “new taxpayer” to make an internal resolution to elect Section 475 MTM on securities only for 2024 within 75 days of Jan. 1, 2024. Otherwise, existing partnerships or S-Corps must file an external 475 election statement with the IRS by March 15, 2024.

 

Year-End Tax Planning For Traders

| By: Robert A. Green, CPA

Join Robert A. Green, CPA of GreenTraderTax.com, in his webinar on year-end tax planning for traders. Don’t wait until tax time in April; arrange tax savings before year-end. Learn about deferring income, accelerating deductions, tax-loss selling, avoiding wash sale losses, paying estimated taxes, Roth IRA conversions, S-Corp payroll with health and retirement benefits, SALT cap workaround strategies for pass-through entities, and other tax-savings strategies. Mr. Green will cover recent tax law changes that affect traders.

If you can’t join us live, register and you will automatically receive a link to the recording after the session ends. You don’t have to be a client of IBKR.

How Covid-19 Tax Relief & Aid Legislation Impacts Traders (Updates)

May 31, 2020 | By: Robert A. Green, CPA | Read it on

Tax tips for the July 15 deadline, extensions, 475 elections, NOL carrybacks, CARES relief, and more.

Update June 29: “IRS today announced the tax filing and payment deadline of July 15 will not be postponed. Individual taxpayers unable to meet the July 15 due date can request an automatic extension of time to file until Oct. 15 – it is not an extension to pay any taxes due. For people facing hardships, including those affected by COVID-19, who cannot pay in full, the IRS has several options available to help.” (See Taxpayers should file by July 15 tax deadline; automatic extension to Oct. 15 available.)

Watch our Webinar or recording Last-Minute Tax Tips & Extensions For Traders.

Original post

Congress postponed the tax filing and payment deadline from April 15 to July 15, 2020, for 2019 individual tax returns, extensions, and 2020 elections (i.e., Section 475). That’s good news for sole proprietor traders.

The July 15 deadline also applies to calendar-year 2019 C-Corps, U.S. residents abroad, estates, trusts, gift tax returns, information returns, IRA, and HSA contributions originally due April 1, or later.

Partnerships and S-Corps
Calendar-year 2019 partnership and S-Corp tax returns and 2020 Section 475 elections for partnerships and S-Corps were due March 16, 2020. These pass-through tax returns and entity 475 elections are not eligible for the July 15 postponement deadline because the March 16 deadline was before April 1. IRS virus relief guidance mentions pass-through entities, but that’s for a fiscal-year partnership or S-Corp tax return due on or after April 1, 2020.

Traders have calendar-year partnerships and S-Corps, so their entities are not eligible for the July 15 postponement relief. Some asked our firm if their existing partnership or S-Corp could take advantage of the postponed deadline for making a 2020 Section 475 MTM election. The answer is no.

Extensions for individual taxpayers
If you need more time to file your 2019 individual income tax return, file an automatic extension (Form 4868) for three additional months until October 15, 2020.

If you cannot pay the taxes you owe for 2019, then it’s essential to file the one-page extension to avoid IRS late-filing penalties of 5% per month for up to five months. The IRS charges this penalty based on the tax balance due. On Form 4868, enter your estimate of total tax liability for 2019, total 2019 payments, including overpayment credits, balance due, and the amount you’re paying. “If your return is more than 60 days late, the minimum penalty is $330 (adjusted for inflation) or the balance of the tax due on your return, whichever is smaller.” Even if you cannot pay any amount due, filing the extension on time avoids the late-filing penalty.

The IRS also charges late-payment penalties if the taxpayer does not pay at least 90% of their 2019 tax liability by the postponed deadline of July 15, 2020. The late-payment penalty is 0.5% per month, for up to five months, for a maximum of 2.5%. It’s ten times less than the late-filing penalty. For example, if the taxpayer owes $50,000 by July 15 but doesn’t pay it until October 15, 2020, the total penalty is $750 (three months of 0.5% equals 1.5% times $50,000).

The IRS allows the taxpayer to request abatement of late-payment and late-filing penalties based on a “reasonable cause.” Contracting coronavirus in your family or being negatively impacted by the virus might constitute a reasonable cause. “Attach a statement to your return, fully explaining the reason. Don’t attach the statement to Form 4868.”

The IRS calculates penalties and interest based on the tax payment paid after July 15.

The current interest rate on late payments is 4.5%, and the IRS does not forgive interest charges.

2020 estimated taxes
Treasury also postponed Q1 and Q2 quarterly estimated tax payments for 2020 until July 15, 2020. The original due dates were April 15 for Q1 and June 15 for Q2. Third and fourth quarters keep their original due dates of September 15, 2020, and January 15, 2021, respectively.

Mark your payment memo “2020 Form 1040-ES,” so the IRS does not confuse it with 2019 tax payments. Consider overpaying the 2019 extension, planning for an overpayment credit to apply to 2020 estimated taxes.

States also postponed the deadline
All states with a personal income tax have extended their April 15 due dates. See AICPA state filing conformity chart that they update.

Check if your state is decoupling from CARES, such as for NOL carrybacks. That’s happened in prior stimulus legislation.

Consider a section 475 election by July 15
If you have 2020 YTD trading losses and are eligible for trader tax status (TTS) as a sole proprietor, consider a 475 election on securities and or commodities due by July 15, 2020, the postponed tax deadline. Many traders have massive trading losses in 2020, and they desperately need a 475 election for ordinary loss treatment to unlock NOL carryback refunds.

Section 475 ordinary losses offset all types of income, which navigates around the $3,000 capital loss limitation. Section 475 securities trades are also exempt from wash-sale loss adjustments, which can create phantom income and capital gains taxes. I call Section 475, “tax loss insurance.” I generally recommend 475 for securities only to retain lower 60/40 capital gains rates on commodities (Section 1256 contracts). Section 475 does not apply to segregated investment positions so that you can enjoy deferral and long-term capital gains treatment, too.

There’s also a 20% QBI deduction on 475 income, net of TTS expenses. QBI excludes capital gains and portfolio income. Trading is a “specified service activity,” so you must be under the taxable income threshold of $326,600/$163,300 (married/other taxpayers) for 2020 to be eligible for the QBI tax deduction on TTS/475 income.

Be careful to follow the election rules properly. Attach a 2020 Section 475 election statement to your 2019 individual income tax return or extension filed by July 15, 2020.

E-filing an extension is convenient, but taxpayers cannot attach an election statement to an e-filed extension. Print the extension, attach the election, and mail or fax them together to the IRS.

If you are ready to file your tax return by July 15, there might be a problem: Most tax preparation software programs for consumers don’t include 475 elections. Either mail the 2019 tax return with 2020 Section 475 election statement attached, or e-file the tax return and send the election to the IRS separately by July 15. (See an example election statement and information about Form 3115 in Green’s 2020 Trader Tax Guide, chapter 2.)

CARES allows five-year NOL carrybacks
Starting with the 2018 tax year, TCJA repealed two-year NOL carrybacks and only allowed NOL carryforwards limited to 80% of the subsequent year’s taxable income. TCJA introduced the “excess business loss” (EBL) limitation, where aggregate business losses over an EBL threshold ($500,000 for married and $250,000 for other taxpayers for 2018) were considered an NOL carryforward. TCJA deferred losses into the future.

CARES suspended TCJA’s EBL limitation for 2018, 2019, and 2020. It also allows five-year NOL carrybacks for 2018, 2019, and 2020 and/or 100% application of NOL carryforwards.

Business owners should consider amending 2018 and 2019 tax returns to remove EBL limitations and consider five-year NOL carryback refund claims. It’s too late to elect 475 ordinary loss treatment for 2018 and 2019; a 2019 Section 475 election was due April 15, 2019. 2020 NOL carrybacks must wait until 2021 unless Congress speeds up that process with more virus legislation.

Businesses have until June 30, 2020, to file a 2018 Form 1045 (quickie refund) for a 2018 NOL carryback. They should get moving on these NOL carrybacks ASAP. Otherwise, they need Form 1040-X, which allows the IRS more time to process the refund.

TTS traders with Section 475 ordinary losses and those without 475 but who have significant NOLs from expenses (i.e., borrow fees on short-selling) should consider NOL carrybacks. If Congress changes the rules again (see below), your refund claim should be respected by the IRS as you filed based on current law in effect at the time.

The House passed new virus legislation
The House recently passed new virus legislation, backtracking on CARES business loss relief. However, the Senate rejected taking up this new House legislation. The House law restricts taxpayers to carry back NOLs from 2019 and 2020 only to tax years beginning on or after January 1, 2018.

The House legislation retains EBL limitations for 2018, 2019, and 2020 and it lifts the SALT limitation for 2020 and 2021. Proponents of the House bill argued that CARES business loss relief mostly benefits the wealthy. Proponents of CARES claim small businesses, plenty of which are not wealthy, need NOL carryback refunds to replenish their capital to remain in business — a goal for virus relief. Opponents of the House bill say lifting SALT helps mostly upper-income taxpayers. Pundits expect Congress to enact more virus legislation, so stay tuned.

CARES tax relief and economic aid
CARES offered tax relief and economic aid to employees, independent contractors, sole proprietors, and other types of small businesses. However, traders don’t fit into usual categories, so there are issues in applying for some CARES tax relief and aid.

Traders generate “unearned income,” and the CARES Act focuses on “earned income” (jobs). Traders eligible for trader tax status (TTS) operating in an S-Corp might be able to receive state and federal unemployment benefits if they close their trading business due to the negative impact of the pandemic.

TTS traders don’t qualify for a loan under the SBA Paycheck Protection Program (PPP), or any other SBA loan because trading is considered a “speculative business,” which the SBA bars from its lending programs.

TTS traders might be eligible for NOL carrybacks, relaxed retirement plan distributions, and recovery rebates.

Taxpayers negatively impacted by Covid-19 can take a withdrawal from an IRA or qualified retirement plan of up to a maximum of $100,000 in 2020 and be exempt from the 10% excise tax on “early withdrawals.” The taxpayer has the option of returning (rolling over) the funds within three years or paying income taxes on the 2020 distribution over three years. CARES also suspended required minimum distributions for 2020.

Here’s an example
My client, Josh, was recently laid off due to Covid-19. He is collecting state unemployment insurance plus federal pandemic relief of $600 per week. Josh is eligible for the $100,000 early withdrawal from his employer 401(k), and he can pay taxes or roll it over during the following three years, depending on how things work out. Josh plans to use a 401(k) early withdrawal of $50,000 to finance a new TTS sole proprietorship.

Josh’s TTS Schedule C does not conflict with his unemployment insurance benefits because he is buying and selling capital assets and not collecting a salary. Josh plans to submit a Section 475 election on securities only for 2020, due by July 15, 2020. He wants tax loss insurance and to be eligible for a 20% QBI deduction.

Next year, after Josh’s unemployment insurance ends, he might form a TTS S-Corp to have a salary in December to unlock health-insurance and retirement-plan deductions. S-Corp salary would conflict with unemployment insurance. (It’s always best to check with your state.) The financial markets are highly volatile in 2020, so there’s an opportunity for traders, especially with zero commissions. Josh operates his trading business from home, where he is safer from the pandemic. Brokers have reported strong growth in new trading accounts.

See blog posts:
April 15 Tax Deadline Moved To July 15 (Live Updates)
Massive Market Losses? Elect 475 For Enormous Tax Savings
How Traders Should Mine the CARES Act For Tax Relief & Aid
Tax Extensions: 12 Tips To Save You Money
IRS Coronavirus Tax Relief

Darren Neuschwander CPA contributed to this blog post.