CHAPTER 8
Investing

Putting money aside for that proverbial rainy day is an admirable and necessary goal but it can be a difficult proposition, especially when your paycheck doesn't seem to stretch far enough. Still, savings and investing are essential to your financial well‐being, and Americans are saving at a growing rate. According to Federal Reserve Bank, the personal savings rate (the ratio of personal savings to disposable personal income) in the United States, which is typically 6% to 7%, increased substantially during the pandemic, and was 9.6% in July 2021. However, during 2022, with the spike in inflation affecting gas prices and food prices, the savings rate dropped to about 5%. Fortunately, the tax laws can help you to make the most of your efforts. It also provides tax breaks if your investments don't work out.

However, for 2018 through 2025, investment‐related expenses that were previously deductible as miscellaneous itemized deductions are not deductible. These include safe deposit box rental fees; subscriptions to investment newsletters, online services, and apps; computers and tables used for investments; and fees for financial advice.

This chapter deals with tax breaks for so‐called taxable accounts and other investments that are not held in tax‐favored retirement accounts. The tax breaks for IRAs and qualified retirement accounts, which are tax‐deferred accounts, can be found in Chapter 5. For more information, see IRS Publication 514, Foreign Tax Credit for Individuals; IRS Publication 525, Taxable and Nontaxable Income; IRS Publication 544, Sales and Other Dispositions of Assets; IRS Publication 550, Investment Income and Expenses; IRS Publication 551, Basis of Assets; IRS Publication 564, Mutual Fund Distributions; and IRS Publication 575, Pension and Annuity Income.

Penalty on Early Withdrawal of Savings

Time deposit accounts and certificates of deposit are fixed for a set term. These savings vehicles, which have been paying very low interest rates in recent years, still generally pay a higher rate of interest than money‐market and passbook accounts. But if they are cashed in before maturity, a bank penalty is imposed. The penalty usually is forfeiture of some interest and, in some cases, even principal. The penalty is tax deductible.

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If you cash in a certificate of deposit (CD) or savings account before its fixed maturity date for any reason (such as you need the money to pay personal expenses or you can obtain a higher interest rate if you move the money), you may be forced to pay a penalty. The penalty is subtracted from the funds you receive.

You can deduct this penalty, which may be a forfeiture of interest and/or principal (if the penalty exceeds the interest), even though you do not itemize your other deductions. In the case of savings certificates with fixed maturities of longer than one year, your deduction is based on the forfeiture of original issue discount (which is nothing more than a way of figuring interest). Regardless of the maturity involved, this deduction is called a penalty on early withdrawal of savings. There is no dollar limit on this deduction.

Conditions

There are no conditions or requirements to meet. As long as you take money out of a savings certificate before the specified maturity date and are subject to a penalty, you can deduct the penalty in full.

Planning Tip

When putting money into time‐savings vehicles, such as certificates of deposit, don't extend the investment period beyond the time you may need the funds so that you can avoid early withdrawal penalties if you do need the money then. Consider splitting your savings into multiple savings certificates with different maturity dates so that you can readily have access to some funds penalty free.

Pitfalls

You cannot net the penalty against the interest you receive and eliminate the need to separately deduct the penalty. You must report all of the interest on the savings certificate and then separately deduct the early withdrawal penalty.

The above‐the‐line deduction for the penalty on early withdrawals from savings accounts does not apply to the 10% early distribution penalty usually imposed on withdrawals from qualified retirement plans and IRAs before age 59½.

Where to Claim the Benefit

The forfeited amount is reported to you (and the IRS) on Form 1099‐INT if the certificate of deposit is for one year or less, or on Form 1099‐OID if the certificate of deposit is for longer than one year. You deduct this amount on Schedule 1 of Form 1040 or 1040‐SR.

Loss on Bank Deposits

During the Great Depression, there was a run on the banks; depositors rushed to withdraw their money, forcing many banks to go under. Today, there are many protections in place (such as state‐mandated funding requirements and Dodd‐Frank, a federal law) to ensure the integrity of banks. But despite these protections, some banks still fail. Losses suffered by depositors of failed banks that are not insured by the Federal Deposit Insurance Corporation (FDIC) or funds not covered by FDIC protection may be tax deductible under certain conditions.

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If your bank goes under and your account is not covered in whole or in part by FDIC insurance, you can deduct your loss.

Historically, there have been different ways to treat your loss (each of which is explained in the next section):

  • Bad debt deduction
  • Casualty loss, but this option doesn't apply for 2018 through 2025
  • Ordinary loss, but this option is also barred for 2018 through 2025

For 2022, your only option is to claim a bad debt deduction.

Conditions

The conditions for deducting your loss on bank deposits are simple: The bank must be insolvent or bankrupt so that there is no reasonable prospect of recovering your money, and your deposits must not be covered by FDIC or state insurance. Additional conditions and limits, however, may apply to the deduction method you select.

BAD DEBT

You can opt to treat your loss as a bad debt, which is classified for tax purposes as a short‐term capital loss (regardless of how long your money was on deposit). This means you can deduct your loss against capital gains. If you do not have capital gains or if these losses are greater than your capital gains, you can only deduct up to $3,000 against your ordinary income. Any unused amount of the loss can be carried forward and used in a future year.

There is one condition for selecting this deduction method: There must be no reasonable prospect of recovery from the insolvent or bankrupt bank. You must wait until the year in which your nonrecovery becomes clear.

The rules for bad debts are explained more fully in Chapter 11.

CASUALTY LOSS

Before 2018, you could opt to treat your loss as a casualty loss, which means you itemized deductions to claim the loss. The amount of your loss was reduced by $100 right off the top—the $100 subtraction is a feature in the tax law for claiming a casualty loss deduction. Other limitations applied. This option does not apply for 2018 through 2025.

ORDINARY LOSS

Prior to 2018, you could opt to deduct up to $20,000 ($10,000 if you are married and file a separate return) as a miscellaneous itemized deduction, which is subject to the 2%‐of‐AGI floor. Because miscellaneous itemized deductions subject to the 2%‐of‐AGI floor are suspended for 2018 through 2025, this option cannot be used for 2022.

Planning Tip

Why rely on tax write‐offs to make you whole? The best option is to make sure that your deposits are adequately covered by FDIC insurance. Understand your FDIC limits so you don't expose your savings to potential loss, especially when you have accounts in separate institutions that have merged or been taken over.

The rules on FDIC coverage and a listing of the banks with this insurance protection may be found at www.fdic.gov. You can also use the Electronic Deposit Insurance Estimator (EDIE) at www.fdic.gov/edie/ to see where you stand in terms of FDIC coverage for your checking and savings accounts, money market accounts, and certificates of deposit.

Pitfall

The biggest problem with bank losses is knowing exactly what your losses really are. You may recover something when the bank's finances are settled, even if it is only pennies on the dollar. Generally the trustees of a troubled bank will give you an estimate of your expected recovery and loss.

Where to Claim the Benefit

A bad debt is reported on Form 8949, Sales and Other Dispositions of Capital Assets. Be sure that your loss is entered in parentheses to indicate a loss amount. This is then entered on Schedule D, the amount of which is then reported on page 1 of Form 1040 or 1040‐SR.

Capital Losses

Wouldn't it be great if every investment turned out to be profitable? Unfortunately, this isn't the way things work—despite our best efforts, investments may decline in value. A mere drop in an asset's value isn't a tax loss; there must be an actual transaction that fixes the loss. If a sale produces a loss, it may be tax deductible.

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In today's volatile stock market, as well as trading in cryptocurrencies, it's not uncommon to have losses. Capital losses are deductible in full (there is no dollar limit) as an offset to your capital gains for the year. If your capital losses exceed your gains, up to $3,000 of capital losses can be used to offset ordinary income, such as salary and interest income. If your capital losses are more than this $3,000 limit, you can carry the excess forward indefinitely to be used in a future year. The $3,000 limit has not been increased since 1978.

Understand what capital losses are so that you can plan wisely to get the greatest tax benefit from your losses. Capital losses generally arise on the sale or other disposition of capital assets, such as stocks, collectibles, or real estate. Your loss is the difference between what you receive on the sale and your adjusted basis in the property (usually what you paid for it).

There are 2 classes of capital losses: short‐term losses resulting from assets held one year or less and long‐term losses resulting from assets held more than one year. As a practical matter, while complex rules govern the order in which capital losses are used to offset different categories of capital gains, in the end capital losses can be used to fully offset capital gains.

Conditions

You must sell or otherwise dispose of an asset to have a deductible loss. A mere decline in the value of an asset you continue to hold does not entitle you to claim a loss. There are exceptions to the disposition requirement (e.g., a bad debt is treated as a short‐term capital loss even though the debt is not sold or otherwise disposed of).

As mentioned earlier, the loss must be with respect to a capital asset. And this asset must be held for investment or business purposes. You cannot deduct a capital loss on an asset held primarily for personal purposes (such as your home, personal car, or boat).

Planning Tips

Don't overlook basis adjustments that may increase your loss (by increasing your basis). Take into account:

  • Stock dividends you reinvested in the same company
  • Brokers' commissions
  • Acquisition costs (e.g., attorney's fees to handle the purchase of real estate)
  • Selling costs (e.g., real estate broker's fees)

At year‐end, review your investment portfolio to see if there are capital losses you want to harvest for tax advantage. But always temper your tax planning with investment considerations. Don't sell only to generate losses; let your investment decisions be driven primarily by economics (e.g., you think the investment will never recover or there are better places to put your investment dollars).

Pitfalls

While you may have an economic loss on a transaction, do not automatically assume it qualifies for capital loss treatment for tax purposes. Certain pitfalls may trip you up.

WASH SALE RULE

You cannot claim a loss if you acquire substantially identical securities within 30 days before or after the date of sale. Under this “wash sale rule,” you do not lose the loss entirely. Instead, you adjust the basis of the newly acquired securities to reflect the loss you could not take. This will enable you to claim the loss when you later sell the newly acquired securities in a transaction that is not subject to the wash sale rule.

What is a substantially identical security? If you sold shares in Peloton at a loss on March 14, 2022, and purchase shares in Peloton on April 10, 2022, you are subject to the wash sale rule. But if you sold shares in GameStop at a loss on March 14 and bought shares in Sony on April 10, the wash sale rule does not apply because these are different companies and their stocks are not substantially identical securities.

If you sell a Netflix bond at a loss on March 14, 2021, bearing an interest rate of 4.625% payable in 2026, and purchase a Netflix bond on April 10, 2022, bearing an interest rate of 3.625% payable in 2030, you are not subject to the wash sale rule. The differences in the coupon rates and maturities of these bonds make them different securities.

Also, if you sell stock at a loss in your personal investment account and then you cause your IRA or other tax‐advantaged account to buy the identical stock within the wash sale period, you cannot take the loss.

OTHER PITFALLS

You cannot claim a capital loss on the sale or other disposition of all property. Some types of property are not classified as capital assets so they do not qualify for capital loss treatment:

  • Business inventory and property held for sale to customers
  • Depreciable business property and rental property
  • Copyrights, literary compositions, letters, or other such property that you created, that you acquired by gifts from the persons who created them, or that were created for you
  • Government publications

If a spouse incurs the capital loss and dies, it can be used only in the year of death. Excess capital losses cannot be carried forward and used by a surviving spouse in a later year.

Also, as mentioned earlier, you may not claim a loss on your personal property, such as on the sale of your residence, vacation property, or personal car. You can claim a loss only on assets held for investment and which are not otherwise excluded from capital loss treatment. While you may view your home as an investment (perhaps your greatest investment), the tax law does not.

INHERITED PROPERTY

As explained earlier, the capital losses you can deduct are the difference between what you receive on the sale or other disposition and your tax basis (usually what you paid for the items). In the case of inherited property that was part of an estate that filed a federal estate tax return, your tax basis for an item of property is reported to you on Form 8971. If you don't receive this form (e.g., the estate is too small to be required to file a federal estate tax return), your tax basis is the value of the property on the date of the decedent's death.

Where to Claim the Loss

To claim capital losses, you must file Form 8949, Sales and Other Dispositions of Capital Assets, and Schedule D to figure the deductible amount. Short‐term transactions are entered in Part I of Form 8949; long‐term transactions are entered in Part II of Form 8949. The form has 3 different ways to determine basis: transactions listed on Form 1099‐B with basis included, transactions listed on Form 1099‐B without basis included, and transactions not reported on Form 1099‐B. You must use a separate Form 8949 for each type of basis determination. Gains and losses are netted in each of these parts and then short‐term gains or losses are carried over to Parts I and II of Schedule D and then netted against long‐term gains or losses in Part III of Schedule D. Make sure that the amount of any loss entered in column (f) of Schedule D is within parentheses to indicate a loss amount.

You enter the amount of your net capital loss from Part III of Schedule D onto Form 1040 or 1040‐SR.

Capital Gains and Qualified Dividends

During the tough economy, investments may not necessarily have paid off. However, you may still have realized some capital gains or received a capital gains distribution from a mutual fund; you may also have received dividends from stocks and equity mutual funds. Normally, net capital gains, capital gains distributions, and qualified dividends are taxed at a top rate of 15%. However, those with taxable income below a threshold amount that depends on filing status have a zero capital gains tax rate. And those with taxable income above a threshold amount that depends on filing status have a 20% capital gains tax rate.

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If you qualify, you pay no tax on net capital gains (net long‐term capital gains in excess of net short‐term capital losses), capital gain distributions from certain mutual funds, and qualified dividends.

Conditions

To qualify for the zero tax rate, your taxable income must be below a set amount. Table 8.1 shows the upper limit for taxable income that you can receive and still have zero tax on capital gains. In the past, this threshold was based on being in the bottom two tax brackets, but now it's a specific dollar amount. The potential zero‐tax income (e.g., qualified dividends) is taken into account in determining whether you fall within this threshold.

TABLE 8.1 2022 Ceiling on Taxable Income for Zero Tax Rate

Filing StatusTaxable Income Limit
Single$41,675
Head of household 55,800
Married filing jointly and surviving spouse 83,350
Married filing separately 41,675

Taxable income is adjusted gross income reduced by the standard deduction or itemized deductions, limited cash contributions to charity by non‐itemizers if this rule is extended for 2022, net disaster losses if the rule is extended for 2022, and the 20% qualified business income (QBI) deduction for owners of pass‐through entities; it does not take tax credits into account.

The gains must be from property held long term (usually more than one year). Capital gains distributions and qualified dividends are identified as such on Form 1099‐DIV.

Planning Tip

Just because taxable income is above the threshold amount for your filing status does not mean you lose out entirely on the zero tax rate. Depending on your filing status, taxable income, and qualified dividends and capital gains, you may be able to use the zero rate for some of your dividends and capital gains.

Pitfalls

Receiving too much income in capital gains can push you into a higher tax bracket and void the use of the zero tax rate. For example, say you are single and you estimate that your taxable income for the year will be $35,000. You then sell property you've held for years at a profit of $10,000. This gain will put you over the $41,675 threshold for your filing status, preventing your gain from being fully tax free.

If your taxable income exceeds the threshold in Table 8.1, you pay a tax rate of 15% on your capital gains. But if your income exceeds the threshold in Table 8.2, the applicable tax rate is 20%.

Where to Claim the Benefit

Dividends and capital gains must be reported on the return, even though they may be tax free because of the zero tax rate. Dividends are reported directly on Form 1040 or 1040‐SR. Capital gains distributions and capital gains must be reported on Schedule D and then on Form 1040 or 1040‐SR.

TABLE 8.2 2022 Taxable Income Triggering 20% Tax Rate

Filing StatusTaxable Income Limit
SingleOver $459,750
Head of householdOver $488,500
Married filing jointly and surviving spouseOver $517,200
Married filing separatelyOver $258,600

Worthless Securities

Investments in a corporation—stocks or bonds—are made with the intention of collecting income and/or making a profit. But some corporations go under and investors are left holding the bag. The tax law allows a deduction for worthless securities. Special rules for losses resulting from Ponzi schemes are discussed later in this chapter.

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If you hold stocks or bonds issued with coupons or in registered form that become worthless, you can deduct your investment. Worthless securities are treated as becoming worthless on the last day of the year in which they actually become worthless. This date governs whether the loss is treated as a short‐term loss (if you held the security no more than one year prior to December 31) or a long‐term loss (if you held the security more than one year prior to December 31).

The loss is treated as a capital loss (discussed earlier in this chapter), even though there is no sale involved. However, if the loss relates to Section 1244 stock (discussed later in this chapter), the loss is treated as an ordinary loss up to $50,000 ($100,000 on a joint return).

Conditions

There are 2 conditions you must meet to write off your investment in worthless securities:

  1. The security must have had some value at the end of the prior year.
  2. The security must have become totally worthless.

VALUE IN THE PRIOR YEAR

To claim a loss in 2022, you must show that the stock or bond had some value on December 31, 2021. Generally, you can learn whether the stock has any value by checking your year‐end statements from brokerage firms holding your investment. If you hold publicly traded stock in your own name rather than in the brokerage firm's name (“street name”), check newspapers for December 31 to see if the stock is listed in the financial section (only stock with a value is listed in the papers). For example, Enron stock officially became worthless on November 17, 2004 (so the loss was claimed on December 31, 2004), even though the corporation filed for Chapter 7 bankruptcy in 2001. (Chapter 7 bankruptcy is a liquidation process used to go out of business forever.) Due to COVID‐19 and various economic conditions, there have been a slew of bankruptcy filings, but most of them as Chapter 11 reorganizations, which do not make their securities worthless. But there were some Chapter 7 filings, such as Beauty Shoppe.

TOTALLY WORTHLESS

The stock or bond must have no value by the end of the year in which you claim the loss. Just because a bond has stopped paying interest or a stock has been delisted does not mean it is totally worthless. If you claim a loss, be prepared to present facts showing your security is worthless. You can assume that it is worthless if the company issuing it:

  • Goes into bankruptcy that results in a liquidation of the company
  • Ceases to do business
  • Becomes insolvent

However, don't assume that a security is worthless if the company has plans to reorganize in bankruptcy. Companies can emerge from bankruptcy and the stock has value.

Planning Tips

If you hold a security that is partially but not wholly worthless, sell it to nail down your loss. For example, if you think a company is on the brink of bankruptcy, try to sell the security so that you can fix the loss. Typically, your brokerage firm will buy it for a nominal amount, enabling you to claim a loss for the difference between your basis (usually what you paid for it) and what you received for it. Or you can abandon the security, which means that you permanently surrender and relinquish all rights in the security and receive no consideration in exchange for the security.

Bonds not issued with interest coupons or in registered form that become worthless result in a bad debt deduction (discussed earlier under “Loss on Bank Deposits”).

You can claim a loss only in the year in which the security becomes totally worthless, but you have 7 years to discover that a security has become worthless. This is because the statute of limitations on amending your return to claim the loss for a worthless security is 7 years rather than the usual 3 years from the due date of your return.

If you are unsure in which year to claim the loss, it is generally advisable to report it in the earliest year you suspect that the worthlessness occurred and then to renew your claim in each subsequent year when the earliest year proves to be incorrect. This requires that you file amended returns to eliminate the loss from the earliest return and report it on a subsequent return.

Pitfalls

Don't let time pass you by. Once the 7‐year period for filing an amended return has passed, your loss can never be claimed. Each year, make sure to check on the status of any questionable securities to make sure you don't overlook a loss write‐off you are entitled to claim.

The amount you can write off for worthless securities is limited to your basis in the stocks or bonds. Even though you may have witnessed soaring prices only to be followed by the wipeout, you cannot benefit in any way from those record highs; your tax loss is limited to your basis, which is usually what you paid for the securities.

Where to Claim the Loss

You report worthless securities on Form 8949, Sales and Other Distributions of Capital Assets (in Part I if the securities were held for no more than one year; Part II if they were held more than one year). In columns (c) and (d) write “Worthless.” Then, in column (f), be sure to enter the amount of your loss in parentheses. Amounts from Form 8949 are then carried over to Schedule D and then Form 1040 or 1040‐SR.

Loss on Section 1244 Stock

Typically, losses on stock are treated as capital losses, which are deductible to the extent of capital gains for the year, plus up to $3,000 of ordinary income. But losses on a special type of stock, called Section 1244 stock after the section in the Internal Revenue Code defining it, can be treated as ordinary losses within set limits.

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If you own stock that qualifies as Section 1244 stock, you can claim an ordinary loss on the sale or worthlessness of the stock. The ordinary loss is limited to $50,000 ($100,000 on a joint return).

Conditions

To be able to treat your loss as an ordinary loss, you must meet the following 2 conditions:

  1. The stock must qualify as Section 1244 stock.
  2. The amount of your loss cannot exceed the dollar limit.

SECTION 1244 REQUIREMENTS

The issuing corporation can be a C or an S corporation. The stock can be common or preferred (provided the preferred stock was issued after July 18, 1984). But all 4 of these conditions must be met:

  1. The corporation's equity cannot be greater than $1 million at the time the stock is issued (including amounts received for the stock).
  2. The stock must be issued for money or property (other than securities). If you inherited the stock or acquired it for services rendered to the corporation, you cannot treat your loss as an ordinary loss.
  3. The corporation must have derived more than half of its gross receipts during the 5‐year period before your loss from business operations (and not from passive income such as investments, rents, or royalties). If the corporation is in business less than 5 years, then it must have derived more than half of its gross receipts from business operations in all of its years in existence.
  4. You must be the original owner of the stock (you cannot have purchased it from the original owner or someone else).

DOLLAR LIMIT

You can treat only the first $50,000 of the loss as an ordinary loss. The limit on a joint return is $100,000, even if one spouse owned the stock in his or her sole name. Losses in excess of this dollar limit may be treated as capital losses (discussed earlier in this chapter).

Planning Tip

You can claim a Section 1244 loss regardless of how you suffer the loss. Whether you sell your stock at a loss or the company goes under, ordinary loss treatment applies if you meet the conditions discussed earlier.

You (and the corporation) must keep certain records and make them available for IRS inspection, if requested. The records should show that the corporation met the qualifications for the stock to be classified as Section 1244 stock. The corporation should keep records on its gross receipts data for 5 years, and you should keep records on what you paid for the stock. If you don't keep these records, you risk losing your ordinary loss deduction.

Pitfall

If you own stock in an S corporation that holds small business stock, the portion of any loss on such stock passed through to you does not qualify as an ordinary loss on Section 1244 stock. Under the technical language of the tax law, only individuals and partnerships can claim Section 1244 losses. Even though S corporations are pass‐through entities like partnerships, they are not eligible to claim Section 1244 losses.

Where to Claim the Loss

An ordinary loss on Section 1244 stock is reported on Form 4797, Sales of Business Property, which you attach to Form 1040 or 1040‐SR. This form is used whether the loss arises from the sale of the stock or from its becoming worthless so that no sale takes place. The amount from Form 4797 is entered on Schedule 1 of Form 1040 or 1040‐SR.

If the amount of the loss exceeds your dollar limit, you treat the excess loss as a capital loss (discussed earlier).

Margin Interest and Other Investment‐Related Borrowing

Interest paid to borrow money for the purpose of making investments is viewed as “investment interest.” The tax law sets strict limits on when and the extent to which investment interest may be deductible.

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You can deduct interest on borrowing from a brokerage firm that uses your brokerage account as collateral if the money is used for investment purposes. This is called margin interest, and the brokerage firm sets the limits on borrowing, interest rate, and other terms of the loan. You can also deduct interest on other loans used to make investments as an itemized deduction to the extent of your net investment income. If your investment interest is more than your net investment income for the year, you can carry the excess interest forward indefinitely and use it in a future year.

Conditions

There are 2 important conditions:

  1. The funds borrowed must be used for investment purposes.
  2. For full deductibility of the interest, you must have net investment income to offset it.

BORROWING FOR INVESTMENT PURPOSES

It is not the source of the borrowing that determines the treatment of the interest but the purpose for which you use the proceeds from the loan. For example, margin interest is not automatically deductible. If you use the loan to buy a personal car, you cannot deduct the margin interest even though the loan arises from your investment account.

If you borrow money to buy stock in a business, interest on the loan is treated as investment interest, not business interest. In contrast, if you buy the assets of a business, the interest is treated as a fully deductible business interest, not investment interest limited to the extent of net investment income.

NET INVESTMENT INCOME

Your investment interest is deductible only to the extent of your net investment income for the year. Investment income includes:

  • Interest income
  • Annuities
  • Royalties

Interest from passive activities that is not classified by the activities as “portfolio income” is not treated as investment income. This includes interest on rental real estate or interest passed through to you from investments in limited partnerships or other pass‐through entities in which you do not materially participate. Property subject to a net lease is not treated as investment property (it is treated as a passive activity). As a practical matter, you simply look at the Schedule K‐1 (and Schedule K‐3 if applicable) sent to you by the entity to see how to classify the passed‐through interest.

You must reduce investment income by investment expenses for the year to arrive at your net investment income. Investment expenses are expenses directly connected with the production of investment income. Examples of other investment expenses are found throughout this chapter.

Planning Tip

You can opt to treat capital gains and/or qualified dividends as investment income. If you make this election, your capital gains and/or dividends are not eligible for preferential tax rates and are instead included as ordinary income.

Generally it is not advisable to make this election because doing so effectively converts income that would otherwise be taxed at no more than 15% or 20% to income taxed at up to 37% (the taxable income thresholds for the 20% rate are listed in Table 8.2 earlier in this chapter). But the election can make sense in some situations; only running the numbers can determine when this is so.

Pitfall

You cannot deduct interest, regardless of the source of the loan, if you use the money to buy or carry municipal bonds (for example, you need to raise cash and you sell your taxable investments while holding on to your municipal bonds).

Where to Claim the Deduction

You figure your investment interest limitation on Form 4952, Investment Interest Expense Deduction. You then enter the deductible amount on Schedule A, which is filed with Form 1040 or 1040‐SR.

Amortization of Bond Premium

If you buy a bond at a price greater than its stated principal (or face) amount, the excess is called bond premium. You may opt to amortize the premium on taxable bonds; in some cases you must amortize bond premium (you don't have any choice).

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If you buy a taxable bond, such as a corporate bond, you can elect in the year of the purchase to begin amortizing the bond premium. This means that each year you own the bond, you can offset the taxable interest received on the bond by the amortizable premium amount.

If you opt to amortize bond premium, reduce the bond's basis by the amount of amortization.

If you buy a tax‐exempt bond, such as a municipal bond, at a premium, you must amortize the bond premium. But you cannot deduct the amortized premium amount. Instead, you reduce the basis of the bond by the amortization for the year.

Conditions

To amortize the bond premium on a taxable bond, you must meet the following 2 conditions:

  1. You elect amortization.
  2. You figure amortization using the constant yield method for bonds issued after September 27, 1985 (other amortization methods apply for earlier bond issues). This is a 3‐step process under which you determine your yield, the accrual periods to use in figuring amortization, and the bond premium. The computation is rather complicated. For more details, see Chapter 3 of IRS Publication 550, Investment Income and Expenses.

Planning Tips

It is usually advisable to elect amortization so you can offset current interest income from the bond. If you do not make the election, you will probably realize a capital loss when the bond is redeemed at par or you sell it for less than you paid for it.

You do not have to elect amortization for taxable bonds held in IRAs or qualified retirement plans. Since the interest is not currently deductible, no offset is necessary.

Pitfall

If you want to amortize bond premiums on taxable bonds, you generally must elect to do so by attaching your own statement to the return indicating this choice. The election applies to all taxable bonds you own and to those you buy in later years.

Once you have made your choice, you can't change it unless you receive the written approval of the IRS. To request a change, you must file Form 3115, Application for Change in Accounting Method.

Where to Claim the Deduction

The amortizable amount of a premium is not a separate deduction. Instead, it is an adjustment to the interest reported on Schedule B of Form 1040 or 1040‐SR. Report the bond's interest and then subtract the amortization, noting “ABP Adjustment” next to it.

If the amortization exceeds the amount of interest reported, the excess can be deducted as a miscellaneous itemized deduction on Schedule A of Form 1040 or 1040‐SR. This deduction is not subject to the 2%‐of‐adjusted‐gross‐income floor, so it is deductible in 2022 even though deductions subject to the 2%‐of‐AGI floor are not.

Municipal Bonds

States, local governments, and their agencies raise money to operate through the sale of bonds. They pay interest on the bonds as inducements to investors to buy the bonds (i.e., lend them money). The federal government generally exempts this interest from taxes; there may or may not be any state income tax breaks as well.

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Interest on municipal bonds is not subject to federal income tax. You may fully exclude this interest from income. There is no dollar limit.

The exclusion applies to both interest on individual bonds and interest from mutual funds holding municipal bonds.

Conditions

Interest is classified as municipal bond interest only if the bond is issued by a state or local government or government agency.

Planning Tip

Interest on municipal bonds may also be exempt from state income taxes. Table 8.3 shows you how the states treat municipal bond interest. The U.S. Supreme Court has decided that it is permissible for a state to tax the interest earned on out‐of‐state bonds while exempting the interest from in‐state bonds.

Pitfalls

Municipal bond interest can affect the amount of taxes you pay on your Social Security benefits. Municipal bond interest, while exempt from federal income tax, is taken into account in determining your provisional income, the figure used to fix the taxable portion of Social Security benefits at 85%, 50%, or zero. For Medicare recipients, the tax‐free municipal bond interest may also impact whether you are subject to additional premiums for Parts B and D.

TABLE 8.3 State Income Tax Treatment of Municipal Bond Interest

StateState Income Tax Treatment
Alaska, Florida, Nevada, South Dakota, Tennessee, Texas, Washington, and WyomingNo state income tax (so interest on municipal bonds is not taxed).
Alabama, Arizona, Arkansas, California, Colorado, Connecticut, Delaware, Georgia, Hawaii, Idaho, Indiana*, Kentucky, Louisiana, Maine, Maryland, Massachusetts, Michigan, Minnesota, Mississippi, Missouri, Montana, Nebraska, New Hampshire, New Jersey, New Mexico, New York, North Carolina, North Dakota, Ohio, Oregon, Pennsylvania, Rhode Island, South Carolina, Vermont, Virginia, and West VirginiaInterest is exempt from state income tax if the bond is issued by the state in which you file your return (or by Puerto Rico, U.S. Virgin Islands, or American Samoa).
District of Columbia and UtahInterest is tax free regardless of the state of issuance (in Utah interest on out‐of‐state bonds is tax free only if the other state does not tax interest on Utah bonds).
Illinois, Iowa, Kansas, Oklahoma, and WisconsinInterest is fully taxable for state income tax purposes regardless of the state of issuance.

* Out‐of‐state bonds acquired before 2012 are 100% exempt, while bonds acquired after 2011 are subject to Indiana income tax.

Interest on private activity bonds issued after August 6, 1986, while excluded from income for regular tax purposes, is subject to the alternative minimum tax (AMT) (the interest on such bonds issued in 2009 and 2010 continues to be exempt from AMT). These bonds generally pay a slightly higher interest rate than other municipal bonds. However, if you know you will be subject to AMT, it is advisable when making bond investments to forgo the additional interest in favor of municipal bonds not subject to AMT.

Even though interest on municipal bonds is tax free, gain on the sale of the bonds is taxable. For instance, you purchase a bond at par value and sell it 2 years later for $2,000 more than you paid. You have a $2,000 gain that is taxable.

Where to Claim the Exclusion

Even though the interest is fully excludable, you are required to report tax‐exempt interest on your return. You report this interest on line 2a of Form 1040 or 1040‐SR.

Savings Bonds

United States savings bonds were first sold by the federal government in World War I and again in World War II as a way to raise money. Today, these bonds have become a permanent savings vehicle for the millions of Americans who own them. They can be purchased only online at www.treasurydirect.gov.

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Tax on the interest on series E, EE, and I bonds can be deferred until the bonds are cashed in or reach their final maturity dates.

Conditions

Deferral is automatic; you don't have to take any action to receive this tax treatment. You simply do not report the interest annually on your return.

Planning Tips

You can opt to report interest on these savings bonds annually instead of using deferral. This option may make sense when the bondholder has little or no other income so that the interest is taxed at a low rate, if at all.

The U.S. Treasury has changed the way in which interest on series EE bonds is computed. Rather than adjusting the interest semiannually, bonds sold on or after May 1, 2005, now pay a fixed rate until redemption or maturity (e.g., 0.10% for bonds purchased from May 1, 2022, to October 31, 2022). As a result, Series I bonds may be a better option because their interest rate still adjusts semiannually for inflation. For example, I bonds purchased from May 1, 2022, through October 31, 2022, pay a variable rate of 4.81% plus a fixed rate of 0.00%, for a total rate of 4.81%.

Interest may be tax free if  bonds are redeemed to pay certain higher education costs and other conditions are met (see Chapter 3).

Interest is never subject to state and local income taxes.

You can use a federal tax refund on an original return to purchase up to $5,000 in series I savings bonds. Purchases must be made in multiples of $50. You can request up to 3 different savings bond registrations (e.g., in your name, in your spouse's name, or for someone else). See the instructions to Form 8888, Allocation of Refund (Including Savings Bond Purchases), for details.

Pitfalls

Do not continue to hold a bond beyond its final maturity date. No interest is paid after this date. Bonds reach final maturity in 30 years for series EE and I bonds. E bonds used to have maturies of 30 years or 40 years; the last E bond reached its final maturity in June 2010.

In the past, you could have continued deferral beyond a bond's maturity date by rolling it over into a series HH bond. However, these bonds ceased being issued as of August 31, 2004 (previously issued series HH bonds continue to earn interest).

You cannot redeem an EE or I bond until 12 months after its purchase unless your county has been declared a disaster area. There is a 3‐month interest penalty for bonds redeemed before 5 years.

Where to Claim the Benefit

You do not have to report interest if you want to defer it; no special form or schedule needs to be filed.

Gain on the Sale of Small Business Stock

The government wants to encourage investments in small businesses. To do so, it has created certain tax breaks should these investments turn out to be profitable.

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If you have a gain on the sale of small business stock, you can exclude a percentage of the gain from income (called a Section 1202 exclusion). The portion of the gain that is not excluded is subject to a 28% capital gain rate (unless your tax bracket is below this rate so that the tax rate is limited to your bracket, which is what you would pay on ordinary income). The amount of the exclusion depends on when the stock was acquired. The exclusion is 50% of the gain on stock acquired before February 18, 2009; 75% of the gain for stock acquired after February 17, 2009, and before September 28, 2010; and 100% for stock acquired after September 27, 2010.

Conditions

To qualify to exclude a percentage of the gain from income, the stock must qualify as small business stock and you must meet a holding period requirement.

SMALL BUSINESS STOCK

There are 5 conditions for qualifying as a small business stock:

  1. The issuing corporation must be a C corporation (an S corporation cannot issue small business stock for purposes of rollover or exclusion treatment).
  2. The stock must have been originally issued after August 10, 1993.
  3. The gross assets of the business cannot be more than $50 million when the stock is issued.
  4. The corporation must be an active business (and not a holding or investment company). This requires that at least 80% of the corporation's assets are used in the active conduct of a qualified business. A qualified business is one involved in other than the practice of law, medicine, architecture, engineering, health, performing arts, consulting, actuarial science, financial services, brokerage services, banking, insurance, leasing, farming, hotel or motel management, restaurants, or similar businesses. This means that eligible businesses are in such fields as technology, manufacturing, retail, and wholesale.
  5. You must have acquired the stock for cash or other property or as pay for services. You cannot treat inherited or gifted stock as small business stock.

Holding Period

For rollover treatment, you must have held the stock more than 6 months before the date of sale.

For the special exclusion, you must have held the stock more than 5 years before the date of sale.

Planning Tips

If you acquired qualified small business stock from a C corporation at different times, be sure to track your holding period for each as well as your cost basis in the stock. Then when selling qualified small business stock, you can identify which shares you are selling to optimize your tax position in the year of the sale.

If you don't qualify for the 100% exclusion, you can defer tax on the gain from the sale of Section 1202 stock that you've held for at least 6 months by reinvesting the proceeds in other Section 1202 stock within 60 days of the sale. You must make an election for this deferral.

Pitfall

If you deferred gain on the sale of small business stock, understand that eventually you may pay tax on the gain. You had to reduce the basis in the small business stock acquired during the 60‐day period by the amount of the deferred gain. When you sell this stock, the reduction will effectively increase your gain.

Where to Claim the Exclusion

To exclude a portion or all of your gain, report the entire gain on Form 8949, completing all the columns on that line. Then immediately below the line on which you reported gain in column (a) write “Section 1202 exclusion” and in column (g) enter the amount of the exclusion as a loss (in parentheses).

Gain on DC Zone Assets

In the past, there were about 180 empowerment zones (EZs) in the United States; urban EZs fall under the jurisdiction of the U.S. Department of Housing and Urban Development (HUD). While these zones continue to apply for certain tax breaks (e.g., a special employment tax credit), they no longer entitle those who invested in these zones to defer gain on the sale of their assets by rolling them over. However, certain prior investments in DC Zones may result in tax‐free treatment upon a sale in 2022.

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If you have a gain on the sale of DC Zone assets, you can exclude all of the gain from the sale of assets held more than 5 years in the District of Columbia Enterprise Zone for assets if they were acquired after 1997 and before January 1, 2012. In effect, you are not taxed when you sell these qualified assets.

Conditions

There are 3 conditions for excluding gain on property acquired before January 1, 2012:

  1. The property must be a District of Columbia Enterprise Zone (DC Zone) asset, which includes DC Zone business stock, DC Zone partnership interest, and DC Zone business property (including real or other property integral to a DC Zone business).
  2. You must have acquired the DC Zone assets before January 1, 2012, and held them for more than 5 years before the sale. Obviously, any sale in 2021 meets this time condition.
  3. The gain may not be otherwise treated as recapture income or gain from a sale to a related party.

Planning Tips

To determine whether you own property in a DC Zone, see IRS Publication 954, Tax Incentives for Distressed Communities.

If you own a business that employs people in a qualified empowerment zone, you may be eligible for a special employment tax credit (see Chapter 14).

Pitfall

The election to postpone gain from empowerment zone assets by making a rollover no longer applies; it expired at the end of 2020.

Where to Claim the Benefit

Report the sale of DC zone stock in Part II of Form 8949 as if you weren't electing the exclusion. Enter "X" in column (f), with the amount of the exclusion reported as a negative number in column (g). Report the sale of DC Zone business property on Form 4797, Sales of Business Property.

Gain on Reinvestments in Opportunity Zones

The U.S. Treasury, on states' recommendations, has designated low‐income communities as qualified opportunity zones. If you sell property and reinvest your gain in one of these zones within 180 days of the sale, you can opt to defer the gain from your income. The deferred gain is reported on the earlier of the date you sell the investment or December 31, 2026.

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You can postpone gain on the sale of any property as long as you reinvest it in a qualified opportunity zone through an investment fund. There is no dollar limit on how much gain your can defer; in effect it is limited only by your reinvestment. This deferral opportunity applies only through December 31, 2026.

Conditions

There are 2 conditions:

  1. You usually must make the reinvestment within 180 days of the sale that produces your gain.
  2. The sale must be to an unrelated party.

Planning Tip

There are now more than 200 qualified opportunity zone funds (called “O Funds”) for investors. As with any investment, check on fund managers, investment fees, and the location in which the funds are invested.

Pitfall

Investing in an investment fund in a qualified opportunity zone presents an investment risk and a tax risk. While you get to defer your gain, you must settle up with the government when selling your investment in a qualified opportunity zone fund, or December 31, 2026, whichever is earlier. Your basis in the investment in the fund is deemed to be zero, so all of your resulting gain is taxable. However, if you hold it for at least 5 years, your zero basis is increased by 10% of the gain originally deferred. If you hold it for another 2 years (at least 7 years in total), your basis is increased by another 5% of the gain originally deferred.

Even though you have to recognize gain no later than December 26, 2026, if you continue to hold the investment fund beyond this date there's a special election for a sale of your shares in the investment fund. You can elect to use a basis for an investment held at least 10 years equal to the fair market value of the property on the date of sale.

Where to Elect Deferral

The election to defer gain is reported on Form 8949, Sales and Other Dispositions of Capital Assets. Form 8997, Initial and Annual Statement of Qualified Opportunity Fund (QOF) Investments, must be filed each year you hold any investment in a qualified opportunity fund.

Foreign Taxes on Investments

Investors in foreign companies may pay taxes overseas to other governments. To provide a break so that these investors aren't taxed twice, for federal income tax purposes a deduction or tax credit can be claimed if certain conditions are met.

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If you hold investments in foreign countries, including stocks or mutual funds, you may pay taxes abroad. You can write off foreign taxes you pay in one of 2 ways:

  1. Deduct the taxes as an itemized deduction.
  2. Claim a tax credit for the foreign taxes.

Either way, there is no dollar limit to the benefit you can claim.

Conditions

The foreign tax must be a tax on income similar to U.S. tax. However, you cannot write off any tax imposed by a country designated by the U.S. government as engaging in terrorist activities. These countries are listed in IRS Publication 514, Foreign Tax Credit for Individuals.

Planning Tips

Generally, claiming the credit is more valuable than deducting the foreign taxes. The credit reduces your tax liability dollar for dollar. You do not have to be an itemizer if you claim the credit.

If you opt to claim the credit and the amount of the credit you can use in the current year is limited because of your tax liability, you can carry the excess credit back to the 2 preceding years and then forward for up to 5 succeeding years until it is used up. You can only use a carryback or carryover in a year in which you have income from foreign sources.

You have 10 years in which to change your choice from deduction to credit or credit to deduction. You can file an amended return for a period of up to 10 years to change the treatment of the write‐off on your return.

Pitfalls

You cannot elect to treat some foreign taxes as a deduction while treating others as a credit within the same year. You must opt to use one write‐off method for all your foreign taxes. But you can change your choice from year to year.

You get no benefit for foreign taxes paid on investments held by an IRA. Since the IRA is not a taxpayer, it cannot claim a deduction or credit for the foreign taxes paid by it. This means the funds in your IRA are reduced by these taxes with no offsetting benefit. You may wish to reconsider investments subject to foreign taxes being held in an IRA.

If you are subject to the alternative minimum tax (a shadow tax system to ensure that taxpayers who successfully reduce their regular tax will at least pay some income tax), you lose the benefit of an itemized deduction for foreign taxes, which are not deductible for AMT purposes.

If you have an ownership interest in a foreign corporation with earnings from intangibles (patents, trademarks, copyrights), you may have global intangible low‐taxed income (GILTI), which is included in the corporation's income for the year. As an individual, if you make a special election (called a Section 250 election), you are treated as a corporation for purposes of the tax and can claim a foreign tax credit (subject to an 80% limitation). These rules are highly complex and should be discussed with a tax expert.

You may have to complete Form 8938, Statement of Specified Foreign Financial Assets, and file it with your personal tax return if the value of foreign accounts exceeds certain thresholds (e.g., more than $50,000 at the end of the year if you're single). This is referred to as FATCA because the reporting obligation was created by the Foreign Account Tax Compliance Act. Check the instructions to this form and IRS guidance at www.irs.gov/Businesses/Corporations/Basic-Questions-and-Answers-on-Form-8938 for more details about the foreign assets to which the form applies.

If you own or have authority over a foreign financial account, including a bank account, brokerage account, mutual fund, unit trust, or other type of financial account, with a value exceeding $10,000 at any time during the year, you may be required to file a Report of Foreign Bank and Financial Accounts (FBAR) annually. FinCEN Form 114 is used for this purpose and must be filed for 2022 by April 18, 2023 (the same deadline as the one for your federal income tax return) with a 6‐month filing extension (this extension is automatic). Filing Form 8938 does not relieve you of the obligation to file the FBAR form. Civil penalties for non‐willful FBAR violations are capped at $10,000, but courts are split on whether this applies per account or per form. The U.S. Supreme Court has agreed to decide this matter in the 2022–2023 term, but a decision may not be handed down before June 2023 (see the Supplement for any update). Penalties for willful FBAR violations are even greater.

Where to Claim the Deduction or Credit

Foreign taxes you pay on investments are reported to you (and the IRS) on Form 1099‐INT or Form 1099‐DIV. Use this figure for claiming your deduction or credit.

If you are claiming a deduction for foreign taxes, you must file Schedule A. Your deduction is part of your itemized deductions entered on Form 1040 or 1040‐SR.

If you are claiming the foreign tax credit related to your investments, you may qualify to report it on Schedule 3 on Form 1040 or 1040‐SR (without having to complete Form 1116). This simplified filing option applies if the amount of the foreign tax credit is not more than $300 ($600 on a joint return).

If your foreign tax credit is more than this limit, you must complete Form 1116, Foreign Tax Credit (Individual, Estate, or Trust), and then follow the filing instructions given earlier.

Exercise of Incentive Stock Options

Employees may receive special options, called incentive stock options (ISOs), to buy company stock at attractive prices. The exercise of ISOs is not taxable for regular tax purposes, although the spread between the exercise price and stock price is an adjustment for the alternative minimum tax (AMT) and can result in AMT liability.

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There is no regular tax on the exercise of incentive stock options.

Conditions

Incentive stock options (ISOs) are a type of compensation that must be granted in connection with employment. An ISO gives an employee the right to buy employer stock at a set price (called the strike price) within a set time period, after the ISO vests (i.e., cannot be taken from the employee unless he or she leaves employment). If the strike price is less than the market price, an employee exercising the option buys the stock at a bargain; the spread between the strike price and market price at the time the ISO is exercised is not subject to regular income tax if the following 2 conditions are met:

  1. You must hold the stock acquired through the ISO for more than 2 years from the date the ISO was granted and more than one year after the ISO was exercised.
  2. You must have been continuously employed by the employer granting the ISO from the date of the grant up to 3 months prior to the date on which you exercise the ISO.

If the stock acquired through the ISO is sold prior to the required holding period, then there is taxable compensation and immediate capital gain or loss recognition. The rules are complex; see IRS Publication 525, Taxable and Nontaxable Income.

Planning Tip

If you hold ISOs, determine how many to exercise this year, factoring in their expiration date and the impact on alternative minimum tax.

Pitfall

While there is no regular tax on the exercise of an ISO if certain conditions are met, the spread between the strike price and market price is treated as an adjustment for the alternative minimum tax (AMT). Thus, exercising ISOs can generate or increase AMT liability. In fact, exercising ISOs is the number one reason why individuals are impacted by the AMT.

Where to Claim the Benefit

The exercise of the ISO is not reported on Form 1040 or 1040‐SR, except to the extent it is included on Form 6251, Alternative Minimum Tax—Individuals.

Losses from Investment Ponzi Schemes

During the financial meltdown in 2008 and 2009, some investors discovered that their money had been lost through Ponzi schemes. Unscrupulous financiers collected funds from investors and used new investments to pay off old investors; this worked until they were unable to bring in new investors and the scheme was exposed. While Bernard Madoff, a Ponzi scheme king, was sentenced to a 150‐year prison sentence for these crimes, new schemes continue to come to light.

Under a safe harbor deduction, an investor in a Ponzi scheme can deduct 95% of the “qualified investment” if he or she isn't pursuing any third‐party recovery, or 75% if pursuing or intending to pursue a third‐party recovery. The “qualified investment” is the sum of cash and the basis of property invested in the arrangement over the years, plus income (even so‐called phantom income) derived from the arrangement that was included for federal tax purposes in the investor's income, minus any cash or property withdrawn by the investor from the arrangement. After applying the 95%/75%, the deductible amount is then reduced by any actual or potential insurance or SIPC recovery. The deduction is claimed as a miscellaneous itemized deduction not subject to the 2%‐of‐AGI floor. Find more details in Revenue Procedure 2009‐20.

Deferral of Income in Commercial Annuities

Annuities are contracts with insurance companies to pay income for life or a term of years. They may be used to ensure you never run out of money during your lifetime. According to Insurance Information Institute, there was more than $219.1 billion invested in annuities in the U.S. at the end of 2020.

There are 2 basic types of annuities: fixed and variable. Fixed annuities guarantee a set payout at regular intervals (e.g., monthly) based on a minimum interest rate and the company's projections for its returns. Variable annuities allow you to put your funds in certain types of investment, with the payout dependent on investment performance and, in some cases, cost‐of‐living adjustments. Annuities can be immediate—investing your after‐tax dollars and commencing distributions—or deferred—waiting to receive distributions at some time in the future (e.g., when you retire). Generally, annuities end upon the death of the owner or last joint owner, but some may have a guaranteed payout that will be distributed to heirs if the owner(s) dies before this payout has been made.

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Income that builds up in the annuity over the years is not currently taxed; earnings are deferred until distributions are taken. Usually this occurs when you “annuitize” at a certain age to commence regular distributions for the remainder of the contract. This may be a set number of years or over your life (“single life annuity”) or joint life with a named beneficiary such as a spouse (“joint and survivor annuity”).

Conditions

To defer tax on the investment earnings in the contract, you must adhere to the terms of the contract imposed by the insurance company.

Planning Tips

If you need money before you want to start annuity payouts, you may be able to take a loan from your contract; this is tax free. Such borrowing is limited of course by the value of the annuity. You must pay interest on the loan and meet repayment terms to avoid taxation.

Once annuity payments commence, only the earnings portion is taxable. Amounts representing a return of your investment cost in the contract (your total investment as of the annuity starting date) are not taxed. The information needed to report the taxable amount of payments is provided to you on Form 1099‐R, Distributions from Pensions, Annuities, Retirement or Profit‐Sharing Plans, IRAs, Insurance Contracts, Etc.

Usually, there is automatic federal income tax withholding on annuity payments, but you may choose not to have withholding or to have additional withholding by completing Form W‐4P, Withholding Certificate for Pension or Annuity Payments, and submitting it to the insurance company.

Pitfalls

If you take distributions (not loans) from an annuity before age 59½ or surrender the contract, you may be subject to a 10% early distribution penalty. What's more, there may be surrender charges imposed by the insurance company for canceling the contract.

If the annuity guarantees a certain payout and you die before receiving it, your heirs must report the income portion of the payout as income in respect of decedent.

Where to Claim the Benefit

While you are deferring earnings, you do not have to report anything on your tax return. Once distributions commence, earnings are reported directly on Form 1040 or 1040‐SR.

Losses on Digital Assets

Cryptocurrencies and non‐fungible tokens (NFTs) are digital assets that have value just like property you can see and touch. Losses on digital assets are treated the same as losses on other property.

If you hold digital assets for investment, then losses on the sale of your holdings may be used to offset gains from other digital asset sales as well as sales of other property. The wash sale rule (discussed earlier in this chapter) does not apply to digital assets, although proposed legislation would change this; check the Supplement for any update.

If you acquired digital assets at different times and are selling less than your entire holding, you probably have to treat the items sold as the first ones you acquired (first in, first out). But if you have detailed records, you may opt to designate the items sold as those with the highest tax basis (the ones that cost you the most)—referred to by some tax pros as highest in, first out—as a way to minimize your tax gains. The IRS has yet to rule on determining which tax basis to use for the sale of digital assets.

If you engaged in any transaction involving a digital asset (e.g., cryptocurrency, nonfungible tokens) in 2022, you must answer “yes” to the question on page 1 of Form 1040 or 1040‐SR. A transaction includes buying or selling cryptocurrency, receiving it in exchange for goods, services, or any other property, or transferring it for free (including from an airdrop or hard fork). Instructions to the income tax return say you must answer the question; don't leave it blank.

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