How to Get the IRS to Pre-Approve Your Taxes

IRS to Pre-Approve Your TaxesIt might seem odd, but it is possible to get the IRS to give you a straight-forward and binding answer to ambiguous tax positions in advance. How does this happen, you ask? The answer is through an IRS private letter ruling.

IRS private letter rulings provide many benefits, but they are not easy to obtain. There are costs, potential delays, and even then, you run the risk of not being granted a ruling. This dynamic might seem odd as the entire point of applying for a private letter ruling is to obtain certainty. If your position is weak from a tax law perspective, the government could refuse to rule on it. Alternatively, if the position you are seeking is obviously correct, the government might refuse to rule as well because they don’t like to issue “comfort rulings.” Essentially, the only way to get the government to rule is to make a request regarding a position that is in the middle.

If you believe the tax position in question lies somewhere in the middle, requesting a private letter ruling may make sense. If you are more likely one of the outliers, then requesting a tax opinion usually makes more sense. The problem is that tax opinion, unlike private letter rulings, doesn’t bind the IRS.

Deciding Which Path to Take

If the relative certainty of the tax position in question doesn’t provide enough guidance, how do you decide to go after a tax opinion versus a private letter ruling? To make the choice, it helps to understand more details.

First, tax opinions can cover a broader range of topics and can be written about pretty much anything; rulings cannot. In fact, the IRS has an explicit list of subjects that it will not produce private letter rulings on (they modify it occasionally, but there’s always a list). As a result, the first step is to assess the list as this might make the choice for you.

Second, don’t request a private letter ruling unless there is a good chance you think it will be granted. For one, rulings are not cheap with fees often costing upward of $25,000 to obtain a ruling. If you get a “No” ruling against your position, you can withdraw the request to take the ruling off the books, but you may or may not get the fee back. Moreover, when you withdraw a request for a ruling, the IRS sends a notice to your local IRS field office, potentially flagging your return for audit.

Third, opinions can be quick and obtained in as little as a few days or weeks. Rulings, on the other hand, often take months. Also consider that a request for a ruling must be specific and there is little room for modification after filing. Opinions have more flexibility.

Private Letter Ruling Process

Given the specificity and consequence of requesting a ruling, there are intermediate steps to help you test the water before you go all in. Nearly all ruling requests start by initiating a discussion with the IRS to get their general view on your proposed ruling. After this, the taxpayer usually submits a brief memo covering the facts and ruling they are looking to obtain. Next, there are more meetings either in person or by phone with IRS attorneys involved. At this point, if everything looks good, you can prepare and submit the actual ruling request. If you back out at this point, you avoid triggering any fees (IRS fees – not your lawyers or accountants) or audit notices.

Benefits of a Ruling Versus an Opinion

The reason taxpayers go through the time, expense and effort to obtain rulings instead of opinions is that they have several advantages. First, rulings are binding on the IRS. Second, you don’t need to consider penalty protection. Most of all, they provide certainty. Given the difficulty in obtaining a ruling, they generally make financial sense only when a taxpayer has a seriously substantial tax position in play, or at least will over time, and he wants to protect against future audits and legal challenges.

The Five Key IRS Rules of Taxation for Lawsuit Settlements

IRS Rules of Taxation for Lawsuit SettlementsTaxation for Lawsuit Settlements

Coming out on the winning side of a lawsuit as a plaintiff can be a gratifying feeling, especially if there is a financial settlement involved. There is likely a sense of both relief and vindication. Unfortunately, far too often people are in for a shock when they realize that they must pay taxes on the award. You can even be taxed on your attorney fees! However, a little tax planning can go a long way, especially if you do it before the settlement is finalized and the award is substantial. Below are the five key rules to know so you can make the right move. Taxation for Lawsuit Settlements.

  1. The Origin of the Claim Largely Determines the Tax Consequences
    The taxation of legal settlements is based on the origin or reason of the claim. For example, if you win a wrongful termination suit against an employer, your award will be taxed as both wages and likely some other income for whatever is allocated to emotional damages. On the other hand, if you sue the contractor who built your house for damage caused by his negligence, the settlement might not be deemed income at all and you could treat it as a reduction of the purchase price of the real asset. There are many exceptions in this area, and it always depends on the facts and circumstances of the case.
  2. Physical Injuries Produce Tax-Free Awards, but Emotional Distress and Damages Are Taxable
    Damages received for suits involving a physical injury or illness are tax-free. Suits for emotional distress and defamation are taxable, including the physical symptoms of emotional distress (gastrointestinal problems, etc.). Be careful as the latter can be ambiguous, so agreeing on the nature of a physical symptom as the cause or result of emotional distress is best done with the defendant before you finalize the case.
  3. Allocating Damages
    Legal disputes typically involve several issues and courses of conduct. As a result, settlements typically have multiple types of consideration, each with potentially different tax treatments. If the plaintiff and defendant both agree on the tax treatment before finalizing the case, then you can allocate the total damages to certain categories and save taxes. Such agreements are technically non-binding on the IRS, but they are rarely challenged.
  4. Attorney Fees
    Plaintiffs who use a contingent fee lawyer are typically taxed on receiving 100 percent of the money recovered. This means you have to pay taxes even on the portion of your settlement that the lawyers keep as their fee. This is still the case even if your contingent fees are paid directly by the defendant. In clear cases of physical injury where the entire settlement is non-taxable, there’s no issue – but if your award is taxable, you’ll need to be careful.Take an example where you collect a contingent fee settlement for emotional distress and receive $200,000, with your lawyer taking 30 percent or $60,000. In this case, you’ll typically be liable for taxes on the entire $200,000 and not just the $140,000 you keep. To make matters worse, aside from legal fees in employment and certain whistleblower claims, there’s no corresponding deduction for legal fees. There are potential ways to mitigate this, but tax advice early in the process is key.
  5. Punitive Damages and Interest
    Generally, punitive damages and interest are always taxable. For example, take a case where you are hurt in an automobile crash and receive $100,000 in compensatory damages and another $3 million in punitive damages. The $100,000 is tax-free, whereas the $3 million is taxable.Interest is treated similarly. Even if you receive a tax-free type of settlement, but it took time to finalize the settlement through the pre- or post-judgement process, the interest you receive is taxable. Therefore, it is often advantageous to settle a case instead of having it go to judgement.

Conclusion

The taxation of legal settlements and awards are nuanced and largely depend on the facts and circumstances of the case at hand. There are, however, many opportunities through proper tax planning to minimize the tax consequences, but only if you are proactive and plan early in the process.

2017 vs. 2018 Federal Income Tax Brackets

Single Taxpayers
2018 Tax Rates – Standard Deduction $12,000 2017 Tax Rates – Standard Deduction $6,350
10% 0 to $9,525 10% 0 to $9,325
12% $9,525 to $38,700 15% $9,325 to $37,950
22% $38,700 to $82,500 25% $37,950 to $91,900
24% $82,500 to $157,500 28% $91,900 to $191,650
32% $157,500 to $200,000 33% $191,650 to $416,700
35% $200,000 to $500,000 35% $416,700 to $418,400
37% Over $500,000 39.60% Over $418,400

 

Married Filing Jointly & Surviving Spouses
2018 Tax Rates – Standard Deduction $24,000 2017 Tax Rates – Standard Deduction $12,700
10% 0 to $19,050 10% 0 to $18,650
12% $19,050 to $77,400 15% $18,650 to $75,900
22% $77,400 to $165,000 25% $75,900 to $153,100
24% $165,000 to $315,000 28% $153,100 to $233,350
32% $315,000 to $400,000 33% $233,350 to $416,700
35% $400,000 to $600,000 35% $416,700 to $470,700
37% Over $600,000 39.60% Over $470,700

 

Married Filing Separately
2018 Tax Rates – Standard Deduction $12,000 2017 Tax Rates – Standard Deduction $6,350
10% 0 to $9,525 10% 0 to $9,325
12% $9,525 to $38,700 15% $9,325 to $37,950
22% $38,700 to $82,500 25% $37,950 to $76,550
24% $82,500 to $157,500 28% $76,550 to $116,675
32% $157,500 to $200,000 33% $116,675 to $208,350
35% $200,000 to $500,000 35% $208,350 to $235,350
37% Over $500,000 39.60% Over $235,350

 

Head of Household
2018 Tax Rates – Standard Deduction $18,000 2017 Tax Rates  – Standard Deduction $9,350
10% 0 to $13,600 10% 0 to $13,350
12% $13,600 to $51,800 15% $13,350 to $50,800
22% $51,800 to $82,500 25% $50,800 to $131,200
24% $82,500 to $157,500 28% $131,200 to $212,500
32% $157,500 to $200,000 33% $212,500 to $416,700
35% $200,000 to $500,000 35% $416,700 to $444,500
37% Over $500,000 39.60% Over $444,500

 

Estates & Trusts
2018 Tax Rates 2017 Tax Rates
10% 0 to $2,550 15% 0 to $2,550
24% $2,550 to $9,150 25% $2,550 to $6,000
35% $9,150 to $12,500 28% $6,000 to $9,150
37% Over $12,500 33% $9,150 to $12,500
N/A N/A 39.60% Over $12,500

 

FICA (Social Security & Medicare)
FICA Tax 2018 2017
Social Security Tax Rate: Employers 6.2% 6.2%
Social Security Tax Rate: Employees 6.2% 6.2%
Social Security Tax Rate: Self-Employed 15.3% 15.3%
Maximum Taxable Earnings $128,400 $127,200
Medicare Base Salary Unlimited Unlimited
Medicare Tax Rate 1.5% 1.5%
Additional Medicare Tax for income above $200,000 (single filers) or $250,000 (joint filers) 0.9% 0.9%
Medicare tax on net investment income ($200,000 single filers, $250,000 joint filers) 3.8% 3.8%

 

Education Credits & Deductions
Credit / Deduction 2018 2017
American Opportunity Credit (Hope) 2500 2500
Lifetime Learning Credit 2000 2000
Student Loan Interest Deduction 2500 2500
Coverdell Education Savings Contribution 2000 2000

 

Miscellaneous Provisions
2018 2017
N/A – No longer exists N/A Personal Exemption $4,050
Business expensing limit: Cap on equipment purchases $2,500,000 Business expensing limit: Cap on equipment purchases $2,030,000
Business expensing limit: New and Used Equipment and Software $1,000,000 Business expensing limit: New and Used Equipment and Software $510,000
Prior-year safe harbor for estimated taxes of higher-income 110% of your 2018 tax liability Prior-year safe harbor for estimated taxes of higher-income 110% of your 2017 tax liability
Standard mileage rate for business driving 54.5 cents Standard mileage rate for business driving 53.5 cents
Standard mileage rate for medical/moving driving 18 cents Standard mileage rate for medical/moving driving 17 cents
Standard mileage rate for charitable driving 14 cents Standard mileage rate for charitable driving 14 cents
Child Tax Credit $2,000 Child Tax Credit $1,000
Unearned income maximum for children under 19 before kiddie tax applies $1,050 Unearned income maximum for children under 19 before kiddie tax applies $1,050
Maximum capital gains tax rate for taxpayers with income up to $51,700 for single filers, $77,200 for married filing jointly 0% Maximum capital gains tax rate for taxpayers in the 10% or 15% bracket 0%
Maximum capital gains tax rate for taxpayers with income above $51,700 for single filers, $77,200 for married filing jointly 15% Maximum capital gains tax rate for taxpayers above the 15% bracket but below the 39.6% bracket 15%
Maximum capital gains tax rate for taxpayers with income above $425,800 for single filers, $479,000 for married filing jointly 20% Maximum capital gains tax rate for taxpayers in the 39.6% bracket 20%
Capital gains tax rate for unrecaptured Sec. 1250 gains 25% Capital gains tax rate for unrecaptured Sec. 1250 gains 25%
Capital gains tax rate on collectibles 28% Capital gains tax rate on collectibles 28%
Maximum contribution for Traditional/Roth IRA $5,500 if under age 50 $6,500 if 50 or older Maximum contribution for Traditional/Roth IRA $5,500 if under age 50 $6,500 if 50 or older
Maximum employee contribution to SIMPLE IRA $12,500 if under age 50 $15,500 if 50 or older Maximum employee contribution to SIMPLE IRA $12,500 if under age 50 $15,500 if 50 or older
Maximum Contribution to SEP IRA 25% of eligible compensation up to $55,000 Maximum Contribution to SEP IRA 25% of eligible compensation up to $54,000
401(k) maximum employee contribution limit $18,500 if under age 50 $24,500 if 50 or older 401(k) maximum employee contribution limit $18,000 if under age 50 $24,000 if 50 or older
Estate tax exemption $11,200,000 Estate tax exemption $5,490,000
Annual Exclusion for Gifts $15,000 Annual Exclusion for Gifts $14,000

Avoid IRS Trouble by Reporting Bitcoin Cash

Avoid IRS Trouble by Reporting Bitcoin Cash

IRS guidance on the tax treatment of cryptocurrencies already exists. Right now, the IRS considers cryptocurrencies to be “intangible assets.” As a result, they are subject to capital asset treatment. However, recent developments complicate matters.

On Aug. 1, Bitcoin split into two separate cryptocurrencies – Bitcoin and Bitcoin Cash. The currently issued guidance does not address cryptocurrency splits, also known as fork transactions.

How to Report Your Bitcoin Cash

At the split, Bitcoin Cash’s initial price was set at 9.5 percent of Bitcoin’s unit price of $2,801 – or $266. Holders of Bitcoin received one Bitcoin Cash unit for every Bitcoin they held at the time of the split, making Bitcoin Cash a separate financial instrument. As a result, this makes it taxable – so recipients of Bitcoin Cash should include the transaction on their 2017 income tax returns.

Since a cryptocurrency is not technically a security or a debt-like interest, the transaction is considered neither a dividend nor interest income. So how should you report the transaction? While there is no clear-cut guidance as of yet, the best place to report the transaction is as “Other Income” on Form 1040, since this is where you can report transactions that do not neatly fit anywhere else.

Another reporting alternative is to use Form 8949, where you report the sale of capital assets. If you use this form you would report $266 per unit and offset it with a corresponding 9.5 percent of your Bitcoin cost basis. By transferring a proportional amount of your basis from the original investment you will reduce your taxable income. This reporting method also has the advantage of allowing you to offset the capital gains with capital losses and carryovers. Beware however, that this method is less likely to be accepted by the IRS.

What to Do if You Sold Your Bitcoin Cash

Selling some or all of your Bitcoin Cash means you’ll need to treat it as a capital gain and report it via Form 8949. If you sell any Bitcoin Cash, make sure you report your receipt as “Other Income” per above, since this will then serve as your basis for offsetting your sale. Your selling price would be whatever value you sold it for, less any commissions or fees on the sale. Also, remember that for your 2017 tax return filing, your holding period would start from the split date of Aug. 1, and therefore be short-term.

Why Cryptocurrency Splits Are Not Tax-Free Exchanges

Some will argue that cryptocurrency splits such as Bitcoin Cash qualify as tax-free exchanges; however, this view is unlikely to hold up to IRS scrutiny since none of the corporate reorganization non-recognition events under Section 368 apply. Bitcoin Cash is economically different from Bitcoin, and therefore should be viewed as a new category of financial instrument.

Beware the IRS

Over the past several years, many investors sold cryptocurrencies, including Bitcoin, but did not report any taxable income from the transactions, while others used Section 1031 like-kind exchange laws to postpone taxation. The IRS is none too pleased by all of this and is taking action.

The IRS estimates that hundreds of thousands of U.S. taxpayers failed to report cryptocurrency income sales over the past few years. Combined with the recent meteoric rise in prices, the IRS is hungry for the potential to collect billions in interest, penalties and back taxes.

Recently for example, the IRS summoned a large cryptocurrency exchange (Coinbase) to hand over its customer lists. Subsequently, they reached an agreement to disclose only transactions in excess of $20,000; however, it is clear from this case that the IRS is going to get aggressive on the matter.

Cryptocurrency investors need to be aware of the evolving nature of taxation in this space in order to avoid IRS problems. This is an emerging issue and one on which you can bet the IRS is not going to stand down. As always, consult a tax professional for details about your particular situation.