Traders: Consider Ordinary Loss Election By Tax Deadline

March 22, 2016 | By: Robert A. Green, CPA

Click to read Green's blog post in Forbes.

Click to read Green’s blog post in Forbes.

Traders who qualify for trader tax status (TTS) and have a large trading loss in 2016 should consider filing a 2016 Section 475 MTM (ordinary loss treatment) election statement with their extension or return by the April 18, 2016 due date. Section 475 exempts traders from the capital loss limitation and wash sale loss rules. It’s too late to elect Section 475 for 2015: that election was due last April 15, 2015.

Section 475 allows a choice: an election on securities only, Section 1256 contracts only, or both. Specify such in the election statement. Only traders who qualify for trader tax status may use Section 475 and it applies to active trading in that business activity as a sole proprietor individual or on the entity level. Section 475 doesn’t apply to segregated investment positions, so traders may use long-term capital gains benefits on investments.

The biggest problem for investors and traders occurs when they’re unable to deduct trading losses on tax returns, significantly increasing tax bills or missing opportunities for tax refunds. Investors are stuck with this problem, but business traders with TTS can avoid it by filing timely elections for business ordinary tax-loss treatment: Section 475 mark-to-market (MTM) for securities and/or Section 1256 contracts if elected. (Section 1256 contracts include futures, broad-based indexes, options on futures, options on broad-based indexes and several other instruments.)

By default, securities and Section 1256 investors are stuck with capital-loss treatment, meaning they’re limited to a $3,000 net capital loss against ordinary income. The problem is that their trading losses may be much higher and not useful as a tax deduction in the current tax year. Capital losses first offset capital gains in full without restriction. After the $3,000 loss limitation against other income is applied, the rest is carried over to the following tax years. Many traders wind up with little money to trade and unused capital losses. It can take a lifetime to use up their capital loss carryovers. What an unfortunate waste! Why not get a tax refund from using Section 475 MTM right away?

Business traders qualifying for TTS have the option to elect Section 475 MTM accounting with ordinary gain or loss treatment in a timely fashion. When traders have negative taxable income generated from business losses, Section 475 accounting classifies them as net operating losses (NOLs). Caution: Individual business traders who miss the Section 475 MTM election date (April 18 for 2016) can’t claim business ordinary-loss treatment on trading losses for the current tax year. They will be stuck with capital-loss carryovers.

A new entity set up after April 18, 2016 can deliver Section 475 MTM for the rest of 2016 on trading losses generated in the entity account if the entity files an internal Section 475 MTM election within 75 days of inception. The new entity using Section 475 does not change the character of capital loss treatment on the individual accounts before or after entity inception. The entity is meant to be a fix for going forward; it’s not a means to clean up the past problems of capital loss treatment.

Ordinary trading losses can offset all types of income (wages, portfolio income, and capital gains) for you and your spouse on a joint filing, whereas capital losses only offset capital gains. Plus, business expenses and business ordinary trading losses comprise a NOL, which can be carried back two tax years and/or forward 20 tax years. It doesn’t matter if you are a trader or not in a carryback or carryforward year. Business ordinary trading loss treatment is the biggest contributor to federal and state tax refunds for traders.

There are many nuances and misconceptions about Section 475 MTM, and it’s important to learn the rules. For example, you’re entitled to contemporaneously segregate investment positions that aren’t subject to Section 475 MTM treatment, meaning at year-end you can defer unrealized gains on properly segregated investments. You can have the best of both worlds — ordinary tax losses on business trading and deferral with lower long-term capital gains tax rates on segregated investment positions. We generally recommend electing Section 475 on securities only, so you retain lower 60/40 capital gains rates on Section 1256 contracts. Far too many accountants and traders confuse TTS and Section 475; they are two different things, yet very connected.

Section 475 Election Procedures
Section 475 MTM is optional with TTS. Existing taxpayer individuals and partnerships that qualify for TTS and want Section 475 must file a 2016 Section 475 election statement with their 2015 tax return or extension by April 18, 2016 (April 19, 2016 if you live in Maine or Massachusetts). Existing S-Corps file in the same manner by March 15, 2016.

Election statement. The MTM election statement is one simple paragraph; unfortunately the IRS hasn’t created a tax form for it. It’s a version of the following: “Pursuant to Section 475(f), the Taxpayer hereby elects to adopt the mark-to-market method of accounting for the tax year ended Dec. 31, 2016 and subsequent tax years. The election applies to the following trade or business: Trader in Securities as a sole proprietor (for securities only and not Section 1256 contracts).” If you expect to have a loss in trading Section 1256 contracts, you can modify the parenthetical reference to say “for securities and Section 1256 contracts.” But remember, you’ll give up the lower 60/40 tax rates on Section 1256 contracts. If you trade in an entity, delete “as a sole proprietor” in the statement.

Form 3115 filing. Don’t forget an important second step: Existing taxpayers complete the election process by filing a Form 3115 (change of accounting method) with the election-year tax return. A 2016 MTM election filed by April 18, 2016 is reported and perfected on a 2016 Form 3115 filed with your 2016 tax returns in 2017 – by the due date of the return including extensions. Many accountants and taxpayers confuse this two-step procedure and they file the Form 3115 as step one on the election statement date. The IRS usually sends back the Form 3115, which can jeopardize ordinary-loss treatment.

Key strategy
If you have an individual $50,000 capital-loss carryover going into 2016, and you lose $50,000 in Q1 2016, it’s probably wise to elect Section 475 MTM as a sole proprietor for business ordinary loss treatment — and related tax relief — rather than digging a bigger hole of unutilized capital losses.

You can form a new entity for a “do over” to get back to capital gains treatment, so you can use up your capital loss carryovers. You have 75 days of additional hindsight once the entity commences business to file an internal Section 475 MTM election resolution for the entity trading. You’re hoping to generate capital gains in the entity to use up your remaining capital-loss carryovers and put off the Section 475 MTM election to the following entity year.

For more information on Section 475 and trader tax status, read Green’s 2016 Trader Tax Guide.


Don’t Sweat The Tax Deadline, Just Get An Extension

| By: Robert A. Green, CPA

It’s that time of year again: when birds chirp, buds grow on trees and you lose sleep over the April 15th tax deadline. It doesn’t have to be that way: You should have peace of mind to enjoy springtime. This year, the individual 2015 tax return deadline is April 18, 2016 (April 19, 2016 if you live in Maine or Massachusetts), and a six-month extension is available until Oct. 17, 2016.

Six-month extension of time to file
Take charge of your relationship with the IRS: Request an automatic six-month extension of time to file your federal and state income tax returns. Form 4868 instructions point out how easy it is to get this automatic extension — no reason is required.

It’s an extension of time to file a complete tax return, not an extension of time to pay taxes owed. In good faith, estimate and report on the extension form what you think you owe for tax year 2015 based on your tax information received.

Avoid penalties
Try to pay at least 90% of your actual tax return liability with the extension filing to avoid a late-payment penalty of 0.5% per month, up to a maximum of 25%. Filing a timely extension avoids the more onerous late-filing penalty of 5% per month, up to a maximum of 25%. Refer to Form 4868 for further details.

Here’s an example. Assume your 2015 tax liability is $50,000. You file an extension by April 18 but don’t pay any of your tax liability. You file your actual tax return on the extended due date of Oct. 15, 2016 with full payment. A late-payment penalty applies because you did not pay 90% of your tax liability on April 18. The late-payment penalty is $1,500 (6 months late x 0.5% per month x $50,000). Some traders view a late-payment penalty like a 6% margin loan. I’ve seen traders skip an extension payment to trade the tax money longer, only to lose it and cause bigger tax penalties. That’s risky.

By simply filing the extension on time in the above example, you avoided a late-filing penalty of $11,250 (6 months late x 5% per month (25% max), less late-payment penalty factor of 2.5% max, equals a net late-filing penalty of 22.5% x $50,000). Interest is also charged on taxes paid after April 18.

Pay extra with your tax extension
Profitable traders should consider making quarterly estimated tax payments due during the year to avoid underestimated tax penalties. I recommend the following strategy for traders and business owners: Overpay your tax extension on April 15 and apply an overpayment credit toward Q1 current-year estimated taxes. Most traders don’t make estimated tax payments until Q3 and or Q4, when they have more visibility on trading results. Why pay estimated taxes for Q1 and Q2 if you incur large trading losses later in the year?

It’s a better idea to add a cushion to your 2015 tax liability and payment with the extension filing. That gives you three good choices: You’ll have a cushion on 2015 if your estimates of tax liability are low, you can apply an overpayment credit toward 2016 taxes or you may request a tax refund for 2015 if no estimated taxes are due.

Benefits from filing extensions
Sophisticated and wealthy taxpayers know the real tax deadline is Oct. 17, 2016 for individuals and Sept. 15, 2016 for pass-through entities, including partnership and S-Corp tax returns.

You don’t have to wait until the last few days of the extension period like most wealthy taxpayers. Try to file your tax return in the summer months, when IRS and state auditor’s are on vacation. I think audit percentages drop after April 18.

I’ve always advised clients to be aggressive but legal with tax-return filings and look conservative with cash (tax money). Impress the IRS with your patience on overpayment credits and demonstrate you’re not hungry and perhaps overly aggressive to generate tax refunds. It’s a wise strategy for traders to apply overpayment credits toward estimated taxes owed on current-year trading income. You want to look like you’re going to be successful in the current tax year.

The additional time helps build tax positions like qualification for trader tax status in 2015 and 2016. It may open opportunities for new ideas on tax savings. A rushed return does not.  For example, a large trading gain or loss during the summer of 2016 could affect some decision-making about your 2015 tax return. It’s like having the stock market results of April 18 a day early on April 17.

The extension also pushes back the deadline for paying money into qualified retirement plans including a Solo 401(k), SEP IRA and defined benefit plan. If you did a Roth IRA conversion in 2015, you’ll have six months of additional time to recharacterize (unwind) the conversion. That may come in handy, if the stock market drops in Q2 and Q3 2016.

Working with accountants
Your accountant can prepare extension forms quickly for a nominal additional cost related to that job. There are no fees from the IRS or state for filing extensions.

Your accountant begins your tax compliance (preparation) engagement and he or she cuts it off when seeing a reliable draft to use for extension filing purposes. Your accountant will wait for final tax information to arrive after April 18 to complete your tax return. Think of the extension as a half-time break. It’s not procrastination; accountants want tax returns finished.

Please don’t overwhelm your accountants the last few weeks and days before April 18 with minor details on your tax return in a rush to file a complete tax return. Accounting firms with high standards of quality have internal deadlines for receiving tax information for completing tax returns. It’s unwise to pressure your accountant, which could lead to mistakes or oversights in a rush to file a complete return the last-minute. That doesn’t serve anyone well.

Broker 1099-Bs often come late
It’s difficult for securities traders to file a complete tax return by April 18 considering that many brokers send original and corrected Form 1099-Bs late. In some cases, this occurs just days before April 18, or even after.

In a blog post earlier this tax season, I pointed out how securities Form 1099-Bs are apples vs. oranges when it comes to applying Section 1091 wash sale loss rules for taxpayers. It’s a challenge to reconcile your own trade accounting with 1099-Bs so why stress over this reconciliation before the tax deadline? (Read my blog post Securities Brokers Don’t Tell The Full Story About Wash Sale Losses.)

It’s unwise to rush to file a complete tax return based on a 1099-B that could be corrected after filing. Corrected 1099-Bs based on complex cost-basis regulations have been par for the course the last few years. Why incur the cost and risk of filing an amended tax return? If you don’t reconcile your Form 8949 with the 1099-B, IRS computers will likely send you a tax notice, spotting differences under their matching program. (Read my blog post Traders: Don’t Talk To An IRS Agent Until You Read This.)

Traders should focus on trade accounting
If you know you’ll have a capital loss limitation of $3,000, it doesn’t matter if your capital loss is $50,000 or $75,000 at extension time. Either way, you’ll be reporting a capital loss limitation of $3,000 against other income. In this case, don’t get bogged down with trade accounting and reconciliation with Form 1099-Bs until after April 18.

Consider wash sale loss rules. If you know wash sale loss adjustments won’t change your $3,000 capital loss limitation, you can proceed with your extension filing. But if you suspect wash sale loss adjustments could lead to reporting capital gains rather than losses, or if you aren’t sure of your capital gains amount, focus your efforts on trade accounting well before April 18.  Trade accounting software downloads original transactions, not 1099-B information, so you won’t be held up waiting for 1099-Bs.

For Section 1256 contracts, you can rely on the one-page 1099-B showing aggregate profit or loss. For forex, you can rely on the broker’s online tax reports. Wash sales don’t apply to Section 1256 contracts and forex.

State extensions
Some states don’t require an automatic extension if you’re overpaid; they accept the federal extension. Generally in all states, if you owe taxes, you need to file a state extension with payment. States tend to be less accommodating than the IRS in waiving penalties, so it’s usually wise to cover your state first if you’re short on cash. Check the extension rules in your state.

U.S. citizens and resident aliens abroad
Excerpt from the IRS website: “If you are a U.S. citizen or resident alien residing overseas, or are in the military on duty outside the U.S., on the regular due date of your return, you are allowed an automatic two-month extension to file your return and pay any amount due without requesting an extension. For a calendar year return, the automatic two-month extension is to June 15. If you qualify for this two-month extension, penalties for paying any tax late are assessed from the two-month extended due date of the payment (June 15 for calendar year taxpayers). However, even if you are allowed an extension, you will have to pay interest on any tax not paid by the regular due date of your return (April 15 for calendar year taxpayers).”

Extensions for entities
Tax extensions for pass-through entities are March 15, 2016 for S-Corps and April 18, 2016 for partnerships with an extension due date of Sept. 15, 2016. (Note that the IRS recently changed the rule for next year: 2016 partnership tax returns will be due March 15, 2017 to synchronize with S-Corps.)

Pass-through entities are tax filers, not taxpayers, so the federal extension is simple to prepare without any tax liability. Be sure to file it on time because the late-filing penalty for missing the election is $195 per month per partner or shareholder up to a maximum of 12 months.

Some states have nominal franchise taxes, minimum taxes or excise taxes so check with your state or tax advisor. The state taxes are generally due with the extension filing. March 15 is also the deadline for an existing entity — LLC, C-Corp or general partnership (in most states) to elect S-Corp tax status. And March 15 is the date for existing S-Corps to elect Section 475 MTM treatment.

Click to read Green's blog post in Forbes.

Click to read Green’s blog post in Forbes. It’s a prior and different version.

Tax Tips For Sole Proprietor Traders Preparing 2015 Tax Returns

February 15, 2016 | By: Robert A. Green, CPA

Click to read Green's blog post in Forbes

Click to read Green’s blog post in Forbes

The IRS hasn’t created specialized tax forms for individual trading businesses. Traders enter gains and losses, portfolio income, business expenses and investment expenses on various forms. It’s often confusing. Which form should you use if you’re a forex trader? Which form is best for securities traders using the Section 475 MTM method? The different reporting strategies for the various types of traders make tax time not so cut-and-dried.

Sole proprietor trading business
Other sole-proprietorship businesses report revenue, cost of goods sold and expenses on Schedule C. But business traders qualifying for trader tax status (TTS) report only expenses on Schedule C. Trading gains and losses are reported on various forms, depending on the situation. In an entity, all trading gains, losses and expenses are consolidated on the entity tax return — a partnership Form 1065 or S-Corp Form 1120-S. That’s one reason why I recommend entities for TTS traders.

Sales of securities must be first reported on Form 8949, which then feeds into Schedule D (cash method) with capital losses limited to $3,000 per year against ordinary income (the rest is a capital loss carryover). Capital losses are unlimited against capital gains.

Business traders who elect and use Section 475 MTM on securities report their business trades (line by line) on Form 4797 Part II. MTM means open business trades are marked-to-market at year-end based on year-end prices. Business traders still report sales of segregated investments in securities (without MTM) on Form 8949. Form 4797 Part II (ordinary gain or loss) has unlimited business ordinary loss treatment and avoids capital loss limitations and wash sale loss treatment. Form 4797 losses are counted in net operating loss (NOL) calculations.

Section 1256 contract traders (i.e., futures) should use Form 6781 (unless they elected Section 475 for commodities/futures; in that case, Form 4797 is used). Section 1256 traders don’t use Form 8949 — they rely on a one-page Form 1099-B showing their net trading gain or loss (“aggregate profit or loss”). Simply enter that amount in summary form on Form 6781 Part I. If you have a large Section 1256 loss, consider a Section 1256 loss carryback election to carryback those losses three tax years, but only applied against Section 1256 gains in those years. If you want this election, check box D labeled “Net section 1256 contracts loss election ” on the top of Form 6781.

Forex traders with Section 988 ordinary gains or losses who don’t qualify for TTS should use line 21 (other gross income or loss) on Form 1040. Traders who qualify for TTS should use Form 4797, Part II ordinary gain or loss. What’s the difference? Form 4797 Part II losses contribute to NOL carrybacks against any type of income, whereas Form 1040’s “other losses” do not. The latter can be wasted if the taxpayer has negative income. In that case, a contemporaneous capital gains election is better on the Section 988 trades. If you filed the contemporaneous Section 988 opt-out (capital gains) election, use Form 8949 for minor currencies and Form 6781 for major currencies. Forex uses summary reporting.

Schedule C issues
Sole-proprietor business traders report business expenses on Schedule C and trading income/loss and portfolio-related income on other tax forms, which may confuse the IRS. It may automatically view a trading business’s Schedule C as unprofitable even if it has large net trading gains on other forms. This is one reason why I recommend an entity. To mitigate this red flag, I advocate a special strategy to transfer a portion of business trading gains to Schedule C to “zero it out” if possible.

Transfer trading gains to Schedule C
In some cases, a good strategy for sole proprietorship business traders is to transfer some business trading gains to Schedule C to zero the income out, but not show a net profit. Showing a profit could cause the IRS to inquire about a self-employment (SE) tax, which otherwise trading gains are exempt from. (Traders who are full members of a futures or options exchange are an exception here; they have self-employment income under Section 1402(i) on their exchange-generated trading gains reported on Form 6781.)

This special income-transfer strategy also unlocks the home-office deduction and Section 179 (100%) depreciation deduction, both of which require income. While Section 179 depreciation can look to wage income outside the business, the bulk of home-office deductions can only look to business income. This transfer strategy isn’t included on tax forms or form instructions. It’s my suggested industry-accepted practice to date designed to deal with insufficient tax forms for sole-proprietorship trading businesses, and it must be carefully explained in footnotes — another important strategy for business traders. It also has the effect of allowing Schedule C losses in states like New Jersey that don’t allow them.

There is an alternative to the income-transfer strategy: Report gains from trading (from Form 4797, Form 8949, and Form 6781) on Line 8 of the home-office Form 8829. This is an alternative way to provide the necessary income required to generate a home office deduction. While this alternative method leaves Schedule C with larger losses – which is a red flag — it has the added benefit of reducing self-employment income (SEI) and/or net investment income (NII), thereby lowering SE tax and/or NIT. Consider this method if you have SEI from another Schedule C or K-1 business, or if you owe NIT under Obamacare thresholds. Perhaps you want higher SEI to unlock higher AGI deductions.

Include footnotes
I strongly recommend that business traders always include well-written tax-return footnotes, explaining trader tax law and benefits, why and how you qualify for TTS (business treatment), whether you elected Section 475 MTM or opted out of Section 988, and other tax treatment, such as the income-transfer strategy. If you’re a part-time trader, use the footnotes to explain how you allocate your time between other activities and trading. Including footnotes with your return takes a step to address any questions the IRS may have about your qualification for TTS and the various aspects of its reporting on your return before it has a chance to ask you.

This blog post is an excerpt from Green’s 2016 Trader Tax Guide (Chapter 6).

Securities Brokers Don’t Tell The Full Story About Wash Sale Losses

January 20, 2016 | By: Robert A. Green, CPA

Click to read Green’s blog post on Forbes: Securities Brokers Don’t Tell The Full Story About Wash Sale Losses

It’s an inconvenient truth for brokers that the IRS asks them to report wash sale losses on 1099-Bs differently from the way traders must report wash sale adjustments on income tax returns. Brokers are correct in preparing 1099-Bs, but incorrect in telling clients they should import 1099-Bs into their income tax filings. [...] Click here




Thanks @twcarey for covering this tax story in Barron’s (1/23/16) “Two New Mobile Investing Apps for Millennials,” Divy introduces investing as a social exercise while Clink emphasizes regular savings. Plus, tax advice. Click here for excerpt. 


Don’t Solely Rely On 1099-Bs For Wash Sale Loss Adjustments

January 5, 2016 | By: Robert A. Green, CPA

Click to read Green's blog post: Wash Sale Loss Adjustments Can Be A Big Tax Return Headache

Click to read Green’s blog post: Wash Sale Loss Adjustments Can Be A Big Tax Return Headache

Broker-issued Form 1099-Bs for securities provide cost-basis reporting information, but they don’t provide taxpayers everything they need for tax reporting if the taxpayer has multiple trading accounts or trades equities and equity options.

Brokers calculate wash sales based on identical positions (an exact symbol only) per separate brokerage account. But the wash sale loss rules for taxpayers, Section 1091, requires taxpayers to calculate wash sales based on substantially identical positions (between equities and equity options and equity options at different exercise dates) across all their individual accounts including IRAs — even Roth IRAs.

The best accounting solution for generating a correct and compliant Form 8949 is trade accounting software that’s compliant with Section 1091. Don’t just rely on a Form 1099-B (exception: if there is only one brokerage account, the trading is only in equities, not equity options and there are no cost-basis adjustments including wash sale losses).

Many tax preparers and taxpayers continue to disregard Section 1091 rules, even after acknowledging differences with broker 1099-B rules. They do so at their peril if caught by the IRS.

Securities accounting is challenging
Securities brokers are making advances in tax-compliance reporting. It’s due to Congressional legislation and implementation of IRS cost-basis reporting regulations for which phase-in commenced in 2011. Phase-in is almost complete: Equity option transactions and simple debt instruments acquired on January 1, 2014 or later were reported for the first time on 1099-Bs for tax year 2014. The only cost-basis reporting item remaining to be phased-in is reporting complex debt instruments starting on January 1, 2016 or later. Tax-year 2015 1099-Bs should be the same as in 2014.

Taxpayers report proceeds, cost basis, wash sale loss and other adjustments, holding period and capital gain or loss – short term vs. long-term (held over 12 months) on Form 8949. According to the form’s instructions, taxpayers without wash sale and other adjustments to cost-basis may simply enter totals from broker 1099-Bs directly on Schedule D and skip filing a Form 8949. After all, the IRS gets a copy of the 1099-B with all the details.

But this Form 8949 instruction leads many taxpayers and tax preparers astray with taxpayers thinking they don’t have wash sales when in fact they do have many to report in compliance with IRS wash sale rules for taxpayers, which differ from IRS rules for brokers.

Form 8949 problems: apples vs. oranges with 1099-Bs
In accordance with IRS rules for brokers, a 1099-B reports wash sales per that one brokerage account based on identical positions. The wash sale rules are different for taxpayers, who must calculate wash sales based on substantially identical positions across all their accounts including joint, spouse and IRAs. With different rules for brokers vs. taxpayers (apples vs. oranges), it’s expected that in many cases broker-issued 1099-Bs might report different wash sale losses than a taxpayer must report on Form 8949. A broker may report no wash sales when in fact a taxpayer may have many wash sale losses. A taxpayer may permanently lose a wash sale loss between a taxable and IRA account, but a broker will never report that on a 1099-B. In some cases, a broker can report a wash sale loss deferral at year-end, but the taxpayer may have absorbed the wash sale loss in another account, thereby eliminating this tax problem at year-end.

This problem of different rules on wash sales for brokers vs. taxpayers is still widely unknown by many taxpayers and tax preparers. Far too many continue to omit Form 8949 or file an incorrect Form 8949 relying solely on broker 1099-B reporting when they should be using securities trade accounting software to properly calculate and report wash sale loss adjustments.

A predicament for some tax preparers who do understand the problem is that calculating wash sales correctly leads to un-reconciled differences between Form 8949 and 1099-Bs. Some tax preparers don’t want to draw attention to those differences, fearing IRS notices generated from IRS 1099-B automated matching programs. It’s ironic that the mission of Congress in cost basis legislation was to “close the tax gap” providing more opportunities for matching 1099-Bs, but it may lead to a mess of un-reconciled differences. To better close the tax gap, Congress should realign broker and taxpayer wash sale rules to be the same.

There is one scenario where a taxpayer can solely rely on a 1099-B and skip filing Form 8949 by entering 1099-B amounts on Schedule D: when the taxpayer has only one brokerage account and trades equities only with no trading in equity options, which are substantially identical positions. Plus, the taxpayer must not have any wash sale loss or other adjustments. In that narrow case, there are apples vs. apples — only one account and substantially identical is the same as identical.

This problem of apples vs. oranges is biggest for individuals who tend to have multiple accounts. There is a solution for traders who qualify for TTS. Trade in an entity and elect Section 475 MTM, which is exempt from wash sale rules. Keep investment accounts with far less wash sale loss activity on the individual level.

Section 1091 wash sale rules
Per IRS Publication 550: A wash sale occurs when you (a taxpayer) sell or trade stock or securities at a loss and within 30 days before or after the sale you:

  • Buy substantially identical stock or securities,
  • Acquire substantially identical stock or securities in a fully taxable trade,
  • Acquire a contract or option to buy substantially identical stock or securities, or
  • Acquire substantially identical stock for your individual retirement account (IRA) or Roth IRA.

Wash-sale rules differ between brokers and taxpayers
IRS regulations require brokers to calculate and report wash sales per account based on identical positions (it’s reiterated in Form 1099-B instructions). Here is an example of broker rules: an account holder sells 1,000 shares of Apple stock for a loss and buys back 1,000 shares of Apple stock 30 days before or 30 days after. That’s a wash-sale loss deferred (added) to the replacement position cost-basis. But, if the account holder buys back Apple options instead of Apple stock, according to broker rules it’s not a wash sale because an option is not “identical” to the same company’s stock. Broker computer systems are programmed to calculate wash sales based on an identical symbol, and stock and options and options at different exercise dates have different symbols.

IRS regulations for Section 1091 require taxpayers to calculate wash sales based on “substantially identical” positions. That’s very different from the rule for brokers that require “identical” positions. This can be a big problem or challenge for active traders who trade stocks and options, or just options but with constant changes in exercise dates. Starting in 2014, 1099-Bs included equity options for the first time.

Many brokers report “disallowed wash sales for the year” on 1099-Bs rather than “actual wash sales” at year-end. This causes confusion and anxiety for many taxpayers, who draw the wrong conclusion and may think they have a huge problem at year-end, when they may not. The “disallowed wash sales for the year” number may count the same wash sale over and over throughout the year. What counts more is what wash sales are deferred at year-end, and what ones were permanently lost to IRA accounts.

Don’t get into trouble with the IRS
Many traders and local tax preparers who are not that savvy to the wash sale rules may leap to import 1099-Bs into TurboTax or choose to enter totals directly on Schedule D, omitting Form 8949, but they will probably not comply with Section 1091. In effect, they are using broker rules and unknowingly or willfully disregarding Section 1091. While tax preparers may be covered for malpractice, they will have Circular 230 penalties and ignorance is not an acceptable excuse.

Consider a Section 475 election
Business traders qualifying for TTS are entitled to elect Section 475 mark-to-market (MTM) accounting elected on a timely basis, which exempts them from wash sale loss adjustments and the capital loss limitation. Section 475 business trades are not reported on Form 8949; they use Form 4797 Part II (ordinary gain or loss). Although Section 475 extricates traders from the compliance headaches of Form 8949, it does not change their requirement for line-by-line reporting on Form 4797. We recommend trade accounting software to generate Form 4797. If you elect Section 475, you’ll need that software to calculate your Section 481(a) adjustment, too. (Learn more about the Section 481(a) adjustment in Green’s 2016 Trader Tax Guide Chapter 2.)

Accounting software and services for traders
When it comes to a trading activity, it’s wise to do separate accounting for trading gains and losses vs. expenses. A consumer off-the-shelf accounting program is fine for keeping track of expenses, non-trading income, home office deductions and itemized deductions. But when it comes to trade accounting for securities, these programs are inadequate — you need a specialized securities trade accounting program and/or accounting firm, or in limited cases brokerage firm reporting may be sufficient. On our Website accounting services page, learn more about trade accounting software. Choose our professional accounting service using this software.

Futures accounting isn’t required, as you can rely on the tightly controlled one-page 1099-B with summary reporting, using MTM reporting. Although spot forex accounting could be a nightmare if you try to do it yourself, you can rely on the broker’s annual tax reports and should use summary reporting. Spot forex is not a “covered security,” so there are no Form 1099-Bs.

Green’s 2016 Trader Tax Guide

December 24, 2015 | By: Robert A. Green, CPA


20%-Off Promotion Through Jan. 31.

Executive summary and what’s new in this guide 

Use Green’s 2016 Trader Tax Guide to receive every trader tax break you’re entitled to this tax season. Whether you self-prepare your tax returns using consumer tax preparation software or app, engage a CPA firm or local tax storefront, this guide can help everyone through the process. Many of our tax compliance clients use it to take advantage of our offerings, as an educated consumer is the best customer.

Unfortunately, it may be too late for some tax breaks on your 2015 tax return if you wait until you’re actually filing your taxes. If this is the case, then use this guide to execute these tax strategies — including forming an entity with employee-benefit plan deductions — and elections on time for tax-year 2016.

Business traders are far better off than investors in the tax code

By default, the IRS lumps all traders into “investor tax status,” and investors get penalized in the tax code with restricted investment interest and investment expenses, capital-loss limitations ($3,000 per year), wash-sale loss deferrals, no Section 475 mark-to-market (MTM) election and no employee-benefit plans (retirement and health insurance deductions). Business traders who qualify for trader tax status (TTS), though, are entitled to these tax breaks.

Don’t confuse TTS with the related tax-treatment election of Section 475 MTM accounting, which converts new capital gains and losses into business ordinary gains and losses. Only qualified business traders may use Section 475 MTM; investors may not.

A business trader can assess and claim TTS after year-end and even going back three open tax years. But business traders may only use Section 475 MTM if they filed an election on time, either by April 15 of the current year (i.e., April 15, 2015 for 2015), or within 75 days of inception of a new taxpayer (i.e., a new entity). For more on TTS, see Chapter 1.

Investment expenses are limited to 2% of adjusted gross income (AGI) and they are not deductible for the Alternative Minimum Tax (AMT). Plus, investment expenses exclude home office, education and startup expenses, all important business deductions for qualifying business traders.

Can you deduct 2015 trading losses?

Many traders bought this guide hoping to find a way to deduct their 2015 trading losses. Maybe they qualify for TTS, but that only gives them the right to deduct their trading business expenses.

Securities trading and Section 1256 contract trading receive capital gain/loss treatment by default, and there’s a $3,000 capital loss limitation against ordinary income. Yes, Section 475 MTM would have made those losses business ordinary losses, but you had to file the Section 475 MTM election by April 15, 2015 as an “existing taxpayer.” (New taxpayers may elect Section 475 internally within 75 days of inception.) If you did not do this, you’re stuck with capital loss treatment and your next problem is how to use up a capital loss carryover in the next year(s). If you elect Section 475 by April 15, 2016, your 2016 business trading gains will be ordinary rather than capital. Remember, you need capital gains to use up capital loss carryovers. That creates a predicament that we address in Chapter 2 on Section 475 MTM. Once a trader has a capital loss carryover hole, he needs a capital gains ladder to climb out of that hole and a Section 475 election to prevent digging a bigger hole. An entity is better for electing and revoking Section 475 as needed. In 2015, the IRS changed the law to allow revocation of Section 475 elections.

If you have losses from trading Section 1256 contracts (like futures), you may be in luck if you have Section 1256 gains in the prior three tax years. On the top of Form 6781, you can file a Section 1256 loss carryback election. Business traders may elect Section 475 MTM on Section 1256 contracts, but most elect it on securities only so they can retain the lower 60/40 tax rates on Section 1256 gains. Sixty percent is a long-term capital gain even on day trades.

If you have losses trading spot or forward forex contracts in the Interbank market, you may be in luck. By default, Section 988 for forex transactions receives ordinary gain or loss treatment, which means the capital loss limitation doesn’t apply. But without TTS, the loss isn’t a business loss and if you have negative taxable income, the negative part is often wasted — it’s not a business net operating loss (NOL) or capital loss carryover. Forex traders can file a contemporaneous “capital gains and losses” election in their own books and records to opt out of Section 988, which is wise if you have capital loss carryovers. Contemporaneous means in advance, not after the fact using hindsight. In some cases, this election qualifies for Section 1256(g) lower 60/40 tax rates. See Chapter 3 for more details.

IRS cost-basis saga continues

Accounting for trading gains and losses is the responsibility of securities traders; they must report each securities trade and related wash-sale loss adjustments on IRS Form 8949 in compliance with Section 1091, which then feeds into Schedule D (capital gains and losses). Form 8949 came about after the IRS beefed up compliance for securities brokers starting in 2011, causing headaches, confusion and additional tax compliance cost. Congress found tax reporting for securities to be inadequate and thought many taxpayers were under reporting capital gains. The cost-basis rules are almost fully phased-in. Options and less complex fixed income securities acquired on Jan. 1, 2014 or later were reported for the first time on Form 1099-Bs for 2014. Inclusion of complex debt instruments on 1099-Bs is delayed until Jan. 1, 2016. There are no changes with 1099-Bs between 2015 and 2014 tax years.

Broker-issued securities Form 1099-Bs provide cost-basis reporting information, but they don’t provide taxpayers everything they need for tax reporting if the taxpayer has multiple trading accounts or trades equities and equity options. Brokers calculate wash sales based on identical positions (an exact symbol only) per separate brokerage account. But Section 1091 requires taxpayers to calculate wash sales based on substantially identical positions (between equities and equity options and equity options at different exercise dates) across all their accounts including IRAs — even Roth IRAs. The best accounting solution for generating a correct and compliant Form 8949 is software that’s compliant with Section 1091. Don’t just rely on a Form 1099-B (exception: if there is only one brokerage account, the trading is only in equities, not equity options and there are no cost-basis adjustments including wash sale losses). See Chapter 4 for more about these changes and common taxpayer and tax preparer mistakes. Many tax preparers and taxpayers continue to disregard Section 1091 rules, even after acknowledging differences with broker 1099-B rules. They do so at their peril if caught by the IRS.

Option traders

Option traders generally don’t day trade; rather they execute both simple and complex trades over weekly and monthly time horizons. While many option traders may execute trades only a few days per week, they have a position on almost every day of the week. But three recent trader tax court cases for option traders (Assaderaghi, Nelson and Endicott) indicate the IRS requires more frequency than just trading two days per week. See Chapter 11 for details on these three cases. While trading monthly options may be a challenge for claiming TTS, in the past year we’ve noticed more clients trading weekly options, which is better for TTS. Some options traders set aside capital for active trading in equities, which helps them qualify for TTS.

Futures and forex traders

Futures traders, other Section 1256 contract traders and forex traders have it much easier. Futures brokers report Section 1256 contracts in summary fashion, with mark-to-market accounting for realized and unrealized gains and losses, on a simple one-page 1099-B. Taxpayers can rely on a futures 1099-B to report net “aggregate profit and loss” on Form 6781, Part I. See Chapter 4.

Spot forex is not a “covered security” and it’s not by default a Section 1256 contract. Therefore, spot forex brokers should not issue a 1099-B. Spot forex brokers do offer online tax reports and taxpayers should report the summary amount, with or without attachment of those reports on their tax returns. Section 1091 does not apply to Section 1256 contracts and forex, saving futures and forex traders headaches on wash sales.

Differences for various instruments

There are complexities in sorting through different tax-treatment rules and tax rates. It’s often hard to tell what falls into each category, but in Chapter 3 we cover the many trading instruments and their tax treatment.

Securities have realized gain and loss treatment and they are subject to wash-sale rules and the $3,000 per year capital loss limitation on individual tax returns. Section 1256 contracts — including futures — are marked to market at year-end, so there are no wash-sale adjustments and they have lower 60/40 tax rates. Options have a wide range of tax treatment. An option is a derivative of an underlying financial instrument and the tax treatment is generally the same. Equity options are taxed the same as equities, which are securities. Index options are derivatives of indexes, and broad-based indexes are Section 1256 contracts. Simple and complex equity option trades have special tax rules on holding period, adjustments and more. Forex receives ordinary gain or loss treatment on realized trades (including rollovers) unless you file a contemporaneous capital gains election and in some cases navigate into lower 60/40 tax rates. Physical precious metals are collectibles and if these capital assets are held over one year, sales are subject to the taxpayer’s ordinary rate capped at 28% (the collectibles rate). Bitcoin is an intangible asset taxed like securities. Nadex binary options tax treatment is unclear and we make a case to tax them like swaps with ordinary income or loss. Foreign futures are taxed like securities unless the IRS issues a revenue ruling allowing Section 1256 tax benefits (but that is rare). See Chapter 3 for various tax treatments.

Updates on Section 475 MTM elections

Since Congress changed the 1997 tax law to allow business traders to elect Section 475 MTM, GreenTraderTax has helped thousands of business traders save a fortune in taxes by simply making this free election on time and filing a Form 3115 for automatic change of accounting method (free of IRS fees). We refer to Section 475 as free “tax loss” insurance. If you suffer a trading loss of $100,000, you can receive a full business loss deduction against any kind of income in the current year, or with a NOL two-year carryback and/or 20-year carry forward. Section 475 also exempts traders from wash sale reporting for securities trades reported and marked-to-market on Form 4797. Wash sales still apply to investments in securities. If you have a large capital loss carryover, you need to follow our special strategies for considering and electing Section 475 MTM, since Section 475 ordinary income can’t be offset with capital loss carryovers.

The Poppe tax court ruling in October 2015 exposed weaknesses in the Section 475 MTM election process for existing taxpayers. We include a full analysis of the Poppe case in Chapter 11 and tell traders how to better support their Section 475 election in Chapter 2.

The Poppe tax court also lowered the volume of trades needed to qualify for TTS to 720 trades. Our 2015 guide suggested a volume of 1,000 total trades. It’s still not clear how the IRS wants to count lot size breakdowns and legs of complex option trades. See Chapter 1.

IRS warns Section 475 traders

Increasingly, the IRS is focusing in on a delicate issue for traders: whether or not they properly segregate investment positions from trading positions in form and substance. The Assaderaghi, Nelson and Endicott tax court cases highlight this problem, where the traders owned significant investment portfolios and traded around those positions with options. Sole proprietor traders often have investment positions in trading accounts or in separate accounts designated as investment accounts. Not properly segregating investment positions can poison the well for claiming TTS, and gives the IRS a case to claim the trader is really an investor. It can also confuse application of Section 475 MTM treatment separate from capital gains treatment for investments. Some traders attempt to take Section 475 ordinary loss treatment on investment positions, which is not allowed. Or they avoid mark-to-market at year-end on trading positions. There are many nuances and this code section is widely misunderstood by other tax professionals. For more information, see our blog posts IRS Plays Havoc with Traders Misidentifying Investments and IRS Warns Section 475 Traders. See Chapter 2 for the full details on Section 475 MTM.

Business traders should use entity

Many traders start off with individual accounts, joint accounts and IRAs. Why should they consider an entity trading account? Business traders solidify TTS, unlock employee-benefit deductions, gain flexibility with a Section 475 election or revocation and prevent wash-sale losses with individual and IRA accounts. The IRS can apply Section 267 related party transaction rules if a trader purposely tries to avoid a wash sale loss between an entity and individual account. An entity return consolidates your trading activity on a pass-through tax return (partnership Form 1065 or S-Corp 1120-S), making life easier for you, your accountant and the IRS. Individually held investments are separate from business trading in the entity, which is a different taxpayer. The entity is simple and inexpensive to set up and operate. For more details on entities, see Chapter 7.

Retirement plans

Retirement plans for traders can be used several ways. You can trade in the retirement plan, build it up with annual tax-deductible contributions, borrow money from a qualified plan (not an IRA) to start a trading business and convert it to a Roth IRA for permanent tax-free build-up. There are plenty of pitfalls to avoid like early withdrawals subject to ordinary income tax rates and 10% excise tax penalties, and penalties on prohibited transactions. Avoid IRA-owned LLCs and self-dealing as that blows up the IRA. Tax-free compounded returns in retirement plans are valuable and trading losses are deductible in the sense that future retirement plan distributions are lower.

Annual tax-deductible contributions to retirement plans generally save traders more in income taxes than they cost in self-employment (SE) or payroll taxes. Trading gains are not earned income, so traders use entities to create earned income by paying compensation to themselves through an S-Corp. trading company or S-Corp or C-Corp management company. Compensation payments can also reduce the Obamacare 3.8% Medicare tax on unearned income (Net Investment Tax). A married couple working in the business can save well over $10,000 by establishing defined-contribution Solo 401(k) plans for each of them. Defined-benefit plans can save much more; we cover defined benefit plans in depth in Chapter 8. (One exception: Members of a futures exchange are subject to SE taxes on their trades made on those exchanges.) We also cover tax problems caused when a retirement plan invests in publicly traded partnerships like MLPs. That can generate Unrelated Business Income Tax (UBIT) requiring a Form 990 tax filing with a large tax bill that comes as a nasty surprise to many IRA investors. Chapter 8 delves into various retirement plan options and provides the math so you can see exactly how this tax savings strategy works.

Obamacare taxes

The Obamacare 3.8% Medicare tax on unearned income started in 2013 for taxpayers with AGI over $250,000 (married) and $200,000 (single). In this guide, we focus on what affects traders and investment managers in particular. One key point is that the net investment income tax (NIT) applies on net investment income (NII). Traders can reduce it by deducting their trading and investment expenses, including salaries paid to them and their spouses. There are complex IRS regulations for the three buckets in NII: portfolio, rents and royalties (1), passive entities and investment companies (2), and capital gains and losses (3). Generally, taxpayers can’t use a loss from one bucket against income in another bucket.

Business traders fare well with the final regulations for NII (after we fought for changes to the proposed regulations). With the final regulations, business traders are not disenfranchised from using their business trading losses and expenses for calculating NII. Just be sure to prepare Form 8960 (NIT) correctly.

The Obamacare individual health insurance mandate and related tax penalties for non-compliance, exchange subsidies and premium tax credits applied for the first time on 2014 individual income tax returns. Learn about the Obamacare tax forms and strategies for traders in applying for insurance on Obamacare exchanges to maximize their chance of receiving subsidies and premium tax credits. Trading businesses are generally single or spousal-owned with no or few outside employees so they are exempt from the Obamacare employer mandate/employer penalty effective in 2015/2016. The employer mandate applies on employers with 50 or more employees.

For more information, see Chapter 9 and Chapter 15.

Tax planning

Tax planning is important for traders and we include many smart tax-planning ideas in this year’s guide. See Chapter 9.

Words of caution on TTS

Many IRS and state agents don’t understand or respect individuals pursuing qualification as a trading business. While there is no bright line test for TTS, recent trader tax court cases better defined the volume of total trades required (720 per year per Poppe court), frequency of trades (3-4 days per week) and average holding period (under 31 days per Endicott court). Once an exam starts, it can snowball into other issues. IRS and some state agents often want to challenge TTS if the trader is not a full-time, extremely active trader. And the IRS or state agent can ask about TTS and other issues for the years before and after the tax year examined. Learn tips for dealing with the IRS and states in Chapter 10.

In the past, too many traders brought weak cases to tax court and have failed to defend themselves properly. That was certainly the case again recently with Poppe, Assaderaghi, Nelson and Endicott. Serving up easy wins in exams, appeals, private letter rulings and tax court encourages the IRS and states to further question business traders based on bad legal precedent. When TTS is too difficult to achieve, consider the alternative strategies discussed in Chapter 9. It’s also very important to have good CPAs and tax attorneys who are experts in trader tax law in your corner.

Watch out for bad tax advice: Over the years, other service providers suggested traders could easily deduct pre-business education expenses using C-Corps. This advice is very wrong. We cover what’s allowed and what’s not in Chapter 5.

Proprietary trading

Proprietary trading vs. retail trading is covered in Chapter 12. The challenge for proprietary traders is deducting their business expenses, including home-office expenses. They’re allowed to deduct these expenses even if they trade from the firm’s office whether they are independent contractors or LLC members. We also address how to handle education/prop trading firm hybrids and writing off education or lost deposits. One problem for prop traders who are members of an LLC is the Schedule K-1 does not pass through self-employment income so they can’t make retirement plan contributions or deduct health insurance premiums.

The Poppe tax court construed his proprietary trading firm arrangement to be a disguised retail customer account. This ruling should be a huge concern for the proprietary trading firm industry, especially since regulators warned clearing firms about disguised customer accounts in the past. By agreement, prop traders do not trade their own capital in a retail customer account. They trade a firm sub-account with firm capital and far higher inter-firm leverage than is available with a retail customer account.

Investment management

More traders are rising to the ranks of investment managers. Investment managers seek better tax treatment by using carried-interest (profit allocation) tax breaks passed through in their investment funds. There are tax advantages to receiving a share of capital gains (profit allocation) from fund investors rather than incentive fees from the fund, which otherwise are subject to ordinary tax rates and payroll taxes. Investment managers reduce payroll tax on management fees by using S-Corps. In recent years, both of these breaks have survived repeal talk, but that may not last with tax reform discussions in 2016. TTS, Section 475 MTM and other tax treatment elections are important considerations for hedge fund managers. Learn more about investment management taxation in Chapter 13.

International tax matters

U.S. traders move abroad, others make international investments and non-resident aliens invest in the U.S. How are their taxes handled? When it comes to international tax matters, we focus on the following types of traders: U.S. residents living abroad; U.S. residents with international investments; U.S. residents moving to tax possessions like Puerto Rico (with huge tax breaks); U.S. residents surrendering citizenship or green cards; and non-resident aliens investing in the U.S. with individual accounts or through an entity.

Many traders living in the U.S. have offshore trading and bank accounts to trade on foreign markets. Some offshore brokers encourage traders to form foreign entities as a requirement to get access or to set up a foreign brokerage account, in some cases to avoid CFTC rules limiting forex leverage or Reg T margin rules on securities. Look before you leap: Tax compliance for a foreign entity is significant and there are few to no tax advantages for traders.

Traders with foreign accounts need to learn about Foreign Bank Account Reporting (FBAR), Form 8938 (Statement of Specified Foreign Financial Assets), controlled foreign corporations (CFC), foreign disregarded entities, Passive Foreign Investment Companies (PFIC), tax treaties and more.

Chapter 14 touches upon these topics, along with the IRS’s “come clean” OVDP program, the Foreign Account Tax Compliance Act and CFTC regulations.

S-Corps: Use Accountable Plan Before Year-End

December 16, 2015 | By: Robert A. Green, CPA

One formality of using an S-Corp is that it should have an accountable plan for reimbursing employee expenses, including the employee’s home-office deduction. Without an accountable plan, employees report unreimbursed employee business expenses on Form 2106, which is part of miscellaneous itemized deductions only deductible in excess of 2% of AGI and not deductible for AMT. With proper usage of an accountable plan, the S-Corp reports the deductions on its tax return.

Expense reporting is more relaxed with partnership tax structures. Partners may report unreimbursed partnership expenses (UPE) on their individual tax return Schedule E, including home office deductions from Form 8829. S-corporation shareholders generally cannot deduct unreimbursed business expenses on Schedule E because the shareholders are categorized as employees when performing services for the corporation.

If you don’t have an accountable plan, draft one as soon as possible and use it before year-end. For home office deductions, reference Form 8829 as a guide for the S-Corp for reimbursement.

Click here for a sample accountable plan.

Learn more about accountable plans on our recommended payroll service provider’s Website at

If you need help with an accountable plan, email us at or contact your assigned CPA in our firm.

IRS Increases “Expensing” Amount to $2,500

December 3, 2015 | By: Robert A. Green, CPA

Click to read Green's blog post

Click to read Green’s blog post

In general, a business must capitalize property for purposes of depreciation. For smaller purchases, the IRS allows expensing under its Tangible Property Regulations, since it’s inconvenient to maintain depreciation records on small amounts. The IRS increased the de minimis expensing amount to $2,500 from $500. Although the IRS mentions this rule change is effective for 2016, IRS Notice 2015-82 & News Release IR 2015-133 point out it’s Ok to use for open tax years. That means it’s an excellent year-end tax strategy for 2015.

For example, if a business trader purchases a new workstation in December 2015 for $7,500, try to break down the purchase into separate items with each invoice being under $2,500. For example, purchase the computer separate from the monitors and other equipment. With all items on separate invoices under $2,500, the entire $7,500 can be a 2015 business expense without any capitalization for fixed assets and related depreciation. That leads to faster expensing, tax benefits and less compliance work.

“There is no specific requirement that it must be on separate invoices,” said Darren Neuschwander, CPA. “It can all be on one invoice, but it may draw more IRS attention and require more time to breakout. Separate invoices is good practical guidance to avoid this issue. Under the change, the new $2,500 threshold applies to any such item substantiated by an invoice.”

Learn more in our Dec. 3, 2015 Webinar recording: Year-End Tax Planning For Traders. Scroll to 42:07 to 48:35 in “Trader Tax Status.” It starts with “Great news about…“Expensing.”


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