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AAII, the American Association of Individual Investors
The IRS announced on March 21, 2020, that for any person with a federal income tax payment or a federal income tax return due April 15, 2020, the due date for filing or making payments is automatically postponed to July 15, 2020. Affected taxpayers do not have to file Forms 4868 or 7004. There is no limitation on the amount of the payment that may be postponed. For more details read IRS Notice 2020-18, Relief for Taxpayers Affected by Ongoing Coronavirus Disease 2019 Pandemic.
The IRS announced on March 30, 2020, that the distribution of economic impact (stimulus) payments will begin in the next three weeks and will be distributed automatically, with no action required for most people. Social Security beneficiaries who are not typically required to file tax returns will not need to file to receive a payment. For more information, read the IRS webpage Economic impact payments: What you need to know.
To keep up with IRS news related to the pandemic, visit the Coronavirus Tax Relief section of the IRS website.
The May 2020 issue of the AAII Journal goes into greater depth on these and other changes to tax rules that have been made.
This year’s changes to the tax rules are modest in scope.
After experiencing one tax season under the Tax Cuts and Jobs Act (TCJA), many taxpayers will find filling out their 2019 returns to be a more familiar process. This year’s changes are modest in scope: inflation adjustments, a higher cap on medical expense deductions and a revised Form 1040.
Extenders, fixes to the TCJA and proposed changes to retirement savings accounts had yet to make it through Congress as of press time. Included in this group of bills is the retirement enhancement bill called the SECURE Act.
The SECURE Act passed the House of Representatives but remains blocked in the Senate, even though it has bipartisan support and some Republican senators have asked for it to be brought up for a vote.
The bill would expand access to employer-sponsored retirement plans and raise the age for taking required minimum distributions (RMDs) from 70½ to age 72, among other positive steps. A potential caveat for estate plans would be a mandatory 10-year withdrawal requirement for non-spouses who inherited an individual retirement account (IRA).
The Taxpayer First Act should have more universal appeal. Passed by Congress and signed into law by President Trump over the summer, the law mandates that the Internal Revenue Service (IRS) make several changes. Among them are creating an independent office of appeals to resolve taxpayer disputes, improving customer service and providing more help to victims of identity theft. There is also stronger liability relief for innocent spouses and a requirement to establish better cybersecurity guidelines.
The law does increase the minimum penalty for late filing from $215 to $330 (or 100% of the amount required to be shown as tax on the return, if less) for returns filed after 2019, according to The Kiplinger Tax Letter.
Those of you who are approaching or in retirement should also keep watch of a proposal to adjust the life expectancy tables used for determining RMDs. The proposed revisions use a longer 29.1-year life expectancy, based on 2021 mortality rates, and will reduce RMDs by a modest amount. You can read the details and find out how to give feedback at the National Archive’s Office of the Federal Register’s website: www.federalregister.gov/d/2019-24065.
Going back to the TCJA, the law incorporated the chained consumer price index (CPI) to measure inflation. This figure rises more slowly than the traditional CPI, and many line items are increasing by just 1.6% in 2020 as a result. The small increases follow the 2019 increases of mostly 1.5% to 2.0%. The cumulative impact will cause those of you whose income rose at a faster rate to pay more in tax. It may even bump some of you into a higher tax bracket.
If you owed more than expected or received a larger-than-expected refund for the 2018 tax year and haven’t adjusted your withholdings, consider doing so. The IRS’ Tax Withholding Estimator (www.irs.gov/individuals/irs-withholding-calculator) can help you run the numbers.
For the second consecutive year, Form 1040 is set to change. A draft released by the IRS during the fall shows the return spread out over two pages with approximately double the number of line entries compared to 2018.
Technically there are now three instead of six schedules, but in reality there are still six supplementary forms: 1040 Schedule 1, Part 1 and Part II; Schedule 2, Part 1 and Part II; and Schedule 3, Part 1 and Part II. They cover such things as business income, student loan interest deductions, AMT amounts due, health care tax credit, etc. Capital gains and losses will also now be reported on the form.
Those born before January 2, 1955, have the option to use Form 1040-SR instead. This form has bigger type and is more spaced out. Form 1040-SR should be included with tax software programs.
Most of you won’t notice the changes to Form 1040 unless you print copies of your tax forms. During the initial 2018 tax filing season (through May 23, 2019), 94% of individual tax returns were filed electronically. If you will be among this large group, we suggest printing copies of your forms to review before filing. Doing so may help you catch unintended errors.
The changes to the tax form do nothing to alter the underlying complexity of the tax code. They also don’t alter the deadline for filing taxes. April 15, 2020, falls squarely in the middle of the week, meaning there will be no extra days for procrastinating. Even those of you living in states observing Patriots’ Day or in the District of Columbia (which observes Emancipation Day) won’t have an extra day to file.
Early statistics from CapGainsValet put 2019 to have fewer large mutual fund distributions than 2018. As of November 10, 154 mutual funds announced estimated distributions over 10%. In comparison, 316 funds announced distributions over 10% at a similar point in 2018. These distributions are taxable for shares held in a taxable account—even if you don’t sell your shares of the mutual fund issuing the distribution or choose to have the distributions reinvested.
We’ve added the retirement savings contributions credit (aka the Saver’s Credit) to this year’s guide. Though many of you won’t qualify for it, your children or grandchildren may. Share this guide with them, use it as an excuse to discuss investing and consider buying them a membership to AAII.
Those of you who were affected by hurricanes or wildfires may be eligible for some form of tax relief. The IRS has a dedicated page on its website with links to specific pages for each disaster: www.irs.gov/newsroom/tax-relief-in-disaster-situations.
No matter how the tax laws (and tax forms) evolve in the future, one thing is constant: You will still have to pay taxes. Even with the simplifications made by the TCJA, the tax code is complex; hence the need for tax guides. As has been the case in years past, our tax guide provides an overview of the tax rates and deductions likely to impact the majority of AAII members. Since there are many details, loopholes and pitfalls within the tax code, it is impossible for this guide to provide enough details to cover specific tax situations. If you have questions, consult a tax professional. It is your tax return, and the IRS will hold you responsible for any errors made on it.
A special note of thanks goes out to Mark Luscombe, a principal analyst at Wolters Kluwer Tax & Accounting, for previous assistance in answering detailed questions about the tax code. Sources of information used for this year’s guide also include the Internal Revenue Service, Healthcare.gov, Medicare, the Social Security Administration, The Federal Register and “J.K. Lasser’s Your Income Tax 2019” (John Wiley & Sons, 2018).
You can estimate your 2019 and 2020 tax liabilities on our Tax Forecasting Worksheet. This downloadable Excel spreadsheet will calculate the results based on the data you enter and can be saved for your records.
The TCJA’s revised marginal tax brackets went into effect in 2018. They are 10%, 12%, 22%, 24%, 32%, 35% and 37%. These reduced rates are presently set to expire after 2025.
As discussed, Form 1040 is being completely revised again. Those age 65 or older will have the option to use a new, larger-print return form: 1040-SR.
The limit on IRA contributions will be unchanged in 2020 after having been raised for 2019. Up to $6,000 can be contributed to a traditional and/or Roth IRA for 2019 and again in 2020. The additional catch-up contribution limit is not indexed to inflation and remains at $1,000.
Allowable contributions to a 401(k) plan and similar types of employer-sponsored retirement accounts will increase, however. The maximum contribution will be $19,500 in 2020, a $500 increase. The catch-up contribution will increase by $500 to $6,500, bringing the total allowable amount for qualifying workers age 50 or older to $26,000.
The deduction for state and local taxes (SALT) remains capped at $10,000. The limit applies to state and local income, property and sales taxes. The TCJA put this limit into effect in 2018 and it is not indexed for inflation. It will remain at this level through 2025, barring a legislative change.
Social Security tax is 6.2% for employees and 12.4% for those working in self-employed positions on the first $132,900 of wages. In 2020, the cap on maximum taxable earnings will rise to $137,700, an increase of 3.6%. (For 2019, the cap was raised 3.5%.) Retirees younger than full retirement age who have claimed Social Security benefits can earn up to $17,640 without benefits being withheld. This limit will rise to $18,240 in 2020.
The alternative minimum tax (AMT) exemption is $111,700 for married couples filing jointly and $71,700 for single filers in 2019. In 2020, the exemption will rise to $113,400 and $72,900, respectively. The phaseout levels for 2019 are $1,020,600 and $510,300, respectively. They will increase to $1,036,800 and $518,400, respectively, in 2019. The TCJA’s higher levels are in effect through 2025 and are indexed to inflation.
The TCJA eliminated the personal exemption for the period of 2018 through 2025.
Married couples filing jointly can claim a standard deduction of $24,400, and single filers can claim a standard deduction of $12,200 on their 2019 tax returns. In 2020, the standard deduction will rise to $24,800 and $12,400 for married and single filers, respectively. The standard deduction was raised considerably by the TCJA with the adjustment for the so-called “marriage penalty” maintained. The higher level simplifies reporting for some taxpayers by making it more difficult to claim individual deductions. Depending on family size, it may or may not make up for the loss of the personal exemption.
The $2,000 maximum child tax credit is phased out for married couples filing jointly with modified adjusted gross income (MAGI) above $400,000 ($200,000 for all other filers). Both the credit and the phaseout amounts are in effect for the years 2018 through 2025 and are not indexed to inflation. The credit is refundable up to $1,400 in 2019. The refundable portion is indexed to inflation but will remain at $1,400 in 2020. The refundable portion only applies when the full $2,000 credit cannot be used to offset the taxpayer’s tax liability. Qualifying children must have a Social Security number for the $2,000 credit to be claimed. See IRS Publication 972 for more information.
The rules regarding alimony and separate maintenance payments have changed. Effective January 1, 2019, the spouse making such payments can no longer deduct them, while the payee spouse no longer will report the payments as income. This change applies to divorces and legal separations executed after December 31, 2018, and to previously executed agreements modified after December 31, 2018, that expressly state that the tax law change applies to the modification.
Whether you see a change in your long-term capital gains and dividend tax rates depends on your taxable income and not your marginal tax bracket. Under the TCJA, married couples filing joint returns with taxable income below $78,750 ($39,375 if single) will not owe taxes on capital gains or qualified dividends. Couples with incomes of $78,750 to $488,850 ($39,375 to $434,550 for singles) will pay a 15% tax rate. Filers with income above those levels will pay a 20% tax on long-term capital gains and dividends. These levels are indexed to inflation and will rise in 2020: 0% tax up to $80,000/$40,000 for married and single filers, respectively; 15% up to $496,600/$441,450 for married and single filers; and 20% for those with taxable income above those levels.
To be eligible for the long-term capital gains rate, you must have owned the eligible asset for at least 12 months. The discounted qualified dividend tax rate applies to stock dividends and requires a holding period of at least 61 consecutive days during a 120-day period beginning 60 days before the ex-dividend date. (There is no capital gains tax or dividend taxes for securities held within a retirement account, such as an IRA. See Robert Carlson’s article, “Do’s and Don’ts of IRA Investing,” in the March 2010 AAII Journal for investments that can cause an unexpected tax problem.)
Collectibles, which include gold coins and bars, are taxed at a maximum 28% rate. Funds investing in precious metals, including exchange-traded funds (ETFs), may also be subject to the collectibles tax rate. Check with the fund company if you have questions about the tax status.
Short-term capital gains are taxed as ordinary income.
Married couples filing joint returns with net investment income and modified adjusted gross incomes above $250,000 and single filers with net investment income and modified adjusted gross incomes above $200,000 also must pay the additional 3.8% net investment income (NII) surtax on capital gains and dividends. Collectibles are also eligible for the 3.8% surcharge as well. The $250,000/$200,000 thresholds are not indexed to inflation and will remain the same in 2020.
The tax impact of the Affordable Care Act includes surcharges, higher limits on medical expense deductions, and changes to flexible savings account contributions and carryovers. All of these will remain in effect unless repealed by new legislation.
A 0.9% additional Medicare tax applies to wages, compensation and self-employment income above $250,000 for married persons filing jointly and qualifying widow(er)s, $200,000 for single persons and heads of household and $125,000 for those who are married but filing separately. The tax applies to wages that are subject to the Medicare tax and does not depend on adjusted gross income. Should the additional tax not be withheld from wages (a situation that could occur for dual-income couples or individuals working more than one job), the tax could be subject to a penalty if not paid with estimated taxes or through additional withholdings (you can request that your employer increase the income tax withholding on your W-4). More information about the additional Medicare tax can be found on the IRS website at www.irs.gov/businesses/small-businesses-self-employed/questions-and-answers-for-the-additional-medicare-tax.
A 3.8% surtax on net investment income (NII) applies to the lesser of net investment income or modified adjusted gross income exceeding $250,000 for married persons filing jointly and qualifying widow(er)s, $200,000 for single persons and heads of household and $125,000 for those who are married but filing separately. (These thresholds are not indexed for inflation.) Investment income subject to the tax includes, but is not limited to, taxable interest, dividends, non-qualified annuities, rents and royalties, capital gains and passive income from partnerships. Capital gains from the sale of one’s primary residence are subject to the tax to the extent that the income exceeds the applicable home sale exclusion ($500,000 for joint filers and $250,000 for single filers). Excluded are tax-exempt interest (e.g., municipal bond interest payments), distributions from individual retirement accounts (IRAs) and distributions from qualified retirement plans [e.g., 401(k) plans]. The IRS has answers to common NII surtax questions at www.irs.gov/uac/Newsroom/Net-Investment-Income-Tax-FAQs.
Uninsured medical expenses must exceed 10% of adjusted gross income before they can be claimed as a deduction. The 10% floor applies to all individuals regardless of age for tax year 2019. For 2020, the floor will remain at 10%.
Flexible savings arrangement contributions for 2019 are limited to $2,700 annually. This limit is indexed to inflation, and increases to $2,750 for 2020. At the election of their plan sponsors, employees can either carry over unused balances of $500 into the next plan year or take a grace period of up to two and a half months.
A provision included in the TCJA essentially eliminates the individual mandate to have qualifying health insurance starting in 2019. The former penalty no longer exists.
The shared responsibility mandate of the Affordable Care Act included a mandate requiring adults and children to have minimum essential health coverage expired on December 31, 2018. As of the start of 2019, there is no tax penalty for not having qualifying health insurance. Visit www.irs.gov/aca and www.HealthCare.gov for more information. The latter website also has a calculator for determining whether or not a person or family qualifies for Medicaid or subsidies for purchasing insurance.
Though the mandate has been repealed, the NII and the additional Medicare tax remain in effect. The 0.9% additional Medicare tax applies to wages, compensation and self-employment income above $250,000 for married persons filing jointly and $200,000 for single persons for both 2019 and 2020. More information about these taxes can be found in the “Health Care Reform’s Impact on Taxes” box above.
The floor for deducting medical expenses reverted to 10% of adjusted gross income on January 1, 2019. It will remain at this level in 2020 unless new legislation is passed.
Medical insurance premiums for the self-employed are deductible and can be used to reduce adjusted gross income on Form 1040.
Workers participating in flexible savings accounts (FSA) can carry over up to $500 of unused amounts into the next plan year if their plan sponsor allows them to. Plan sponsors have the choice of either offering employees the ability to carry over up to $500 or allowing employees a grace period of up to two and a half months. Dependent care is also eligible for the grace period option, but not the carryover option.
Contributions to a health savings account (HSA) are allowed for those covered by a high-deductible health care plan (HDHP) and not enrolled in Medicare. The minimum annual deductible for self-only coverage is $1,350; it is $2,700 for family coverage. These amounts will rise to $1,400 and $2,800 in 2020.
The maximum limits for annual deductible and other out-of-pocket expenses in 2019 are $6,750 and $13,500, respectively. They will rise to $6,900 and $13,800, respectively, in 2020.
HSA contributions cannot exceed $3,500 for individual coverage and $7,000 for family HDHP coverage. In 2020, the maximum contributions will be $3,550 and $7,100 for individual and family coverage, respectively. See “Health Savings Accounts” in the July 2016 AAII Journal for more information about these accounts.
As previously stated, many deductions, exemptions and limits that are indexed to inflation under current tax law either will or are projected to increase by about 1.6%.
Some items will increase more on a percentage basis because of how adjustments are incremented. The maximum catch-up contribution to a 401(k) plan or similar type of account will rise by $500 in 2020, to $6,500. This is a 8.3% increase over the 2019 cap of $6,000.
Pay attention to the details, because the inflation adjustments are not being made uniformly. This can be particularly apparent when adjustments are made in round numbers. Plus, not all items are indexed to inflation.
Brokers are required to report the cost basis for stocks purchased after January 1, 2011; mutual fund, ETF and dividend reinvestment program (DRP) shares purchased after January 1, 2012; and options and traditional bonds bought and sold by their clients on or after January 1, 2014. If you bought a stock, fund, option or bond before the aforementioned dates, your broker is not required to report the cost basis.
Certain debt instruments, particularly those that are more complex than traditional bonds, purchased after January 1, 2016, fall under the cost basis reporting rules. These include variable-rate bonds (including inflation-adjusted bonds), stripped bonds and convertible bonds. Excluded from this rule are debt instruments where the principal is subject to acceleration (e.g., mortgage-backed securities) and debt instruments with a fixed-maturity date not more than one year from their date of issue.
If you sold a capital asset in 2019, you will need to fill out Form 8949. See the special write-up in the “Cost Basis” box below for details on the reporting rules.
Cost Basis Reporting for Stocks, Bonds, Funds and Options
Brokers are required to report cost basis for stocks purchased on or after January 1, 2011; mutual fund, exchange-traded fund (ETF) and dividend reinvestment plan (DRP) shares purchased on or after January 1, 2012; and options and traditional bonds purchased on or after January 1, 2014. Brokers are also required to state whether any gain or loss on a sale is short-term or long-term. The rules do not apply to securities and funds purchased before the aforementioned dates.
Traditional bonds and debt instruments purchased on or after January 1, 2014, are subject to the reporting rules. The cost basis of and the proceeds for variable-rate bonds, inflation-indexed bonds, convertible bonds, stripped bonds and other complex debt instruments purchased on or after January 1, 2016, fall under the same reporting rules. Excluded are debt instruments where the principal is subject to acceleration (e.g., mortgage-backed securities) and debt instruments with a fixed-maturity date no more than one year from their date of issue.
Investors have the option of notifying their broker as to how market discounts or interest are treated. Brokers will follow a default method of amortizing bond premiums if not otherwise notified. The rules are complex and we suggest speaking with your brokerage firm about the application of the rules, as well as with a tax professional about the best tax treatment to use.
The type of option owned alters how cost basis is reported. Index options may be subject to different cost basis reporting rules. Again, we suggest speaking with your broker if you have questions about how the cost basis is reported.
A default accounting methodology known as first-in, first-out (FIFO) is used when the purchase of securities (other than a mutual fund or DRP shares) involves more than one transaction. The FIFO method treats the first shares purchased (“first in”) as also being the first shares sold (“first out”). Depending on how the stock has performed, this treatment can result in a larger tax bill (the shares appreciated in value) or a bigger capital loss (the shares fell in value).
For mutual funds and DRP stocks, the adjusted basis must be reported in accordance with the broker’s default method—average cost basis—unless you specify otherwise. As the name implies, the average purchase price for your shares, regardless of when they are acquired, is used to determine the cost basis. You can specify FIFO instead of average cost basis. Another option is specific identification. The specific identification method allows you to choose the specific shares that are sold. This treatment can also result in a larger or a smaller tax bill, depending on how the fund has performed relative to the purchase price of the selected shares. You may be able to use other methods such as highest-in, first-out (HIFO) or last-in, first-out (LIFO). Contact your broker, fund family or DRP program to determine what their default methodology is and what choices you have for selecting methodologies.
If you want your broker or fund family to use a specific methodology other than their default methodology (e.g., FIFO for stocks or average cost for mutual funds), you must notify them. In order to do this, you must provide written instructions to your broker or fund administrator detailing your intentions before the order is executed, not afterward.
Dustin Stamper at Grant Thorton’s National Tax Office emphasized the importance of providing these instructions in writing. If you give your broker or fund family specific instructions and they report a different methodology to the IRS, the only way you can dispute what is on Form 1099-B is to provide a dated copy of your instructions. Stamper said that investors will not be able to retroactively determine which shares were sold; they must provide written instructions at or before the time the shares are sold.
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For a complete tax guide to the buying and selling of your personal investments, download our 2019 Personal Investments Guide. |
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If you use a software program (e.g., TurboTax), a book (e.g., “J.K. Lasser’s Your Income Tax 2020”) or a related aid, check for updates before filing. Doing so will help to ensure that you are using the most up-to-date forms and information.
Part of the complexity of the tax code is determining how taxes will be affected by certain situations. This section gives information on scenarios that potentially may be experienced by many individual investors.
The rule of thumb for how taxable income determines Medicare Part B premiums is that your modified adjusted gross income from two years prior will determine your premiums for the current tax year (e.g., 2020 premiums will be determined by 2018 income). See the “Income, Medicare Part B and Social Security” box for information about 2020 premiums.
Income, Medicare Part B and Social Security
The premiums for Medicare Part B are determined by the amount of modified adjusted gross income (MAGI) reported. MAGI is adjusted gross income plus tax-exempt interest (e.g., interest from municipal bonds). Adjusted gross income (AGI) can be found on IRS Form 1040. AGI includes the taxable portion of Social Security benefits plus taxable distributions from retirement accounts such as required minimum distributions (RMDs).
Medicare Part B premiums are determined by MAGI from two years prior. In 2020, the standard Medicare Part B premium will be $144.60 for individuals filing married joint returns with 2018 household MAGI of $174,000 or less. The monthly premium for 2020 rises to $462.70 for 2018 MAGI above $326,000 but less than $750,000. Couples with MAGI of $750,000 or more will pay $491.60 per month. Individuals filing as singles with 2018 MAGI of $87,000 or less will pay the standard premium of $144.60. Premiums rise to $462.70 for singles with 2018 MAGI of $163,000 up to $500,000 and top out at $491.60 for MAGI of $500,000 or higher. The premiums for various income levels can be found at www.medicare.gov (click on “Your Medicare Costs”).
The calculation for how much of your Social Security benefits are taxed is based on combined income for the current tax year. The Social Security Administration defines combined income as: AGI + tax-exempt interest + one half of your Social Security benefits. The amount of benefits subject to taxation for the 2019 tax year is determined by your 2019 combined income. The table below shows how much of Social Security benefits are taxed.
| Combined Income | Percent of Social Security Benefits Taxed |
| Below $25,000 Single & Head of Household | 0% |
| Below $32,000 Married Filing Jointly | |
| $25,000 to $34,000 Single & Head of Household | up to 50% |
| $32,000 to $44,000 Married Filing Jointly | |
| Above $34,000 Single & Head of Household |
up to 85% of benefits + other income |
| Above $44,000 Married Filing Jointly |
Under the tax code, a couple is considered married for the whole year if, on the last day of the tax year, both people are married and living together, living together in a recognized common law marriage, married and living apart without being legally separated under a decree of divorce or separate maintenance or separated under an interlocutory (not final) decree of divorce.
Widow(er)s are considered married for the whole year in which their spouse died and can file a joint return with their deceased spouse. (If there is a dependent child, other filing statuses may be preferable.) For widow(er)s who remarry before the end of the same tax year, a joint return can be filed with the new spouse. The deceased spouse’s filing status would be married filing separately in this case.
A person’s filing status may be single if they were widowed before the start of the calendar year and did not remarry before the end of the calendar year.
A person who becomes divorced under a final decree by the last day of the year is considered to be unmarried for the whole year.
Same-sex couples are treated as being married for federal tax purposes if they were married in a U.S. or a foreign jurisdiction whose laws authorize the marriage of individuals of the same gender. As such, same-sex spouses must file using either married filing separately or married filing jointly status (certain exceptions apply).
Those in common-law marriages are treated as being married for federal tax purposes if they are living together in a common law marriage recognized in the state where they now live or in the state where the common law marriage began.
Couples in domestic partnerships, civil unions or other similar formal relationships recognized but not denominated as marriage under state law are not considered to be married for federal tax purposes.
The U.S. Securities and Exchange Commission (SEC) requires some money market funds, particularly institutional prime money market funds and tax-free institutional money market funds, to use floating net asset values (NAVs). This means that their NAVs are not pegged to $1 per share, but rather can move above or below that benchmark.
The IRS responded to the SEC’s ruling by saying “No gain or loss is determined for any particular redemption of a taxpayer’s shares in a floating-NAV money market fund. Without a determination of loss, a particular redemption does not implicate the wash-sale rules.” The wash-sale rules disallow a loss being claimed for tax purposes when an investment is sold and a substantially identical investment is purchased within 30 days of the sale.
IRA rollovers are restricted to one per person per year. The limitation does not apply to trustee-to-trustee transfers, meaning you can move funds from broker to broker as many times as you would like. The key is that the funds are transferred directly from one broker to another without the assets being distributed to you. A check payable to you instead of the receiving custodian would trigger the 12-month rule.
Rollovers to or from a qualified plan [e.g., a 401(k) plan] are excluded from the rule. Roth IRA conversions are not subject to the one-year limitation and the IRS will disregard them in terms of applying the one-rollover-per-year limitation to other rollovers. Moving funds between Roth IRAs would, however, trigger the one-year waiting period if a check is made payable to you. (Roth IRA recharacterizations, which undid Roth IRA conversions, were banned by the TCJA effective at the start of 2018.)
There is a 60-day deadline for completing a rollover. Waivers to the deadline will be allowed if certain conditions are met, including, but not limited to, an error by the financial institution making or receiving the contribution, a misplaced distribution check, severe damage to the taxpayer’s principal residence and serious illness. Written certification to a plan administrator or IRA trustee must be submitted by the taxpayer within 30 days after being able to make the contribution to take advantage of the waiver. See IRS Rev. Proc. 2016-47 for more information.
Pretax and aftertax contributions from defined-contribution plans [e.g., 401(k), 403(b) and 457(b) plans] can be assigned to different accounts as long as directions are given to the plan administrator in advance of the distribution. See IRS Notice 2014-54 for more information and examples of various scenarios.
The IRS’ Rollover Chart shows the types of retirement savings accounts funds can be rolled over from and into a different type of retirement savings account. The chart was recreated in the July 2016 AAII Journal (“IRA Rollover Chart: Rules Regarding Rollovers and Conversions”).
The IRS continues to warn about tax scams. An ongoing common scam is a phone call requesting immediate payment, commonly via prepaid debit cards and/or a money wire. The fraudster will often threaten a lawsuit, to call the police or involve federal authorities. Hang up if you receive such a call even if your caller ID suggests the phone number is from emergency services or a law enforcement agency; the IRS never initiates contact via a phone call or an email. If the IRS wants to contact you about a tax matter, you will receive a physical letter sent through the U.S. postal service.
Always restrict access to your Social Security number, monitor your credit reports regularly, consider freezing your credit report and use antivirus and firewall software on your computer. Filing your tax return as early as is reasonably possible can also help. Those in their retirement years should be especially on guard, as the fraudsters are targeting your demographic group. See the “Protecting Yourself Against Tax Scams” box for more information on how to protect yourself against fraud attempts.
Protecting Yourself Against Tax Scams 
The Internal Revenue Service continues to warn about con artists posing as IRS agents. Often initiating contact through a telephone call, the fraudsters claim back taxes and/or penalties are owed. Payment is usually immediately demanded either in the form of prepaid cards or a money wire. Hesitancy to cooperate leads to threats of lawsuits, a call to the police or the involvement of federal law enforcement. Despite what your caller ID may show and how convincing the fraudster sounds, these calls are scams.
Another scam involves identify theft. Criminals obtain Social Security numbers and then file false returns under the victims’ identities in order to receive refunds. When the victim later tries to file a legitimate return, it can be rejected by the IRS.
Other current tax scams include pretending to be a charity—often for a natural disaster area—and asking for personal information, fake emails designed to appear as if they came from the IRS and schemes pitched as opportunities to realize a larger refund. The latter can involve being urged to falsify income, falsely claim fuel tax credits, use tax shelters that sound too good to be true and hiding income offshore. Some criminals will also pose as tax preparers for the sole purpose of engaging in identify theft.
There are steps you can take to protect yourself:
If you suspect you are a victim of identity theft or financial fraud, act immediately. Call your banks, brokerage firms, credit card companies, the major credit bureaus and, in the case of tax fraud, the IRS. If your Social Security number is compromised, fill out IRS Form 14039 and continue to file your taxes as you normally would.
Here is a list of the tax rates, deductions, exemptions, credits and other related items that may apply to your 2019 and 2020 taxes. These numbers reflect the changes made by the American Taxpayer Relief Act of 2012 (ATRA), the 2017 TCJA and the 2020 adjustments released by the IRS as of November 6, 2019.
For 2019, the standard deduction is $24,400 for married couples filing a joint return, $12,200 for those who are single or married filing separate returns and $18,350 for heads of household.
For 2020, the standard deduction will increase to $24,800 for married couples filing a joint return, $12,400 for those who are single or married filing separate returns and $18,650 for heads of household. The now higher standard deduction is adjusted for inflation (in $50 increments) but will revert back to pre-TCJA levels at the end of 2025 if the legislation is not renewed.
The additional standard deduction of $1,300 for the elderly and the blind who are married still applies in 2019 and 2020. For single taxpayers who are elderly or blind and not a surviving spouse, the additional standard deduction is $1,650 in 2019 and 2020.
The TCJA suspended the personal exemption for the years of 2018 through 2025.
The maximum allowed IRA contribution for 2019 is $6,000 ($7,000 for individuals age 50 or older). The contribution limits will be unchanged in 2020 even though they are indexed to inflation. The additional catch-up contribution limit of $1,000 is not indexed to inflation. The contributions can be fully deducted for modified adjusted gross incomes (MAGIs) below $103,000 and $64,000 for married filing joint and single household returns, respectively, for the 2019 tax year. The 2019 exemption is $193,000 for a person filing a married joint return who is not covered by a workplace retirement plan but whose spouse is. In 2020, the phaseout levels for deducting contributions will increase to $104,000 for married filing jointly and $65,000 for singles. It will be $196,000 for those married filing a joint return not covered by a workplace retirement plan but whose spouse is.
In 2019, the maximum annual contribution limit to a 401(k) plan or similar type of defined-contribution plan is $19,000 ($25,000 if you are age 50 or over). The maximum contribution limit will rise to $19,500 and the catch-up contribution will increase by $500 to $6,500 in 2020.
In 2019, the maximum annual contribution for SIMPLE (savings incentive match plan for employees) plans is $13,000 (those age 50 or over can make a maximum catch-up contribution of $3,000). The contribution limit will rise to $13,500 (plus the $3,000 catch-up) in 2020.
Married couples with adjusted gross incomes (AGIs) below $64,000 and singles with AGI below $32,000 in 2019 can qualify for the Saver’s Credit. Those limits are indexed to inflation and will rise to $65,000 and $32,500 in 2020. The credit is equivalent to 50%, 20% or 10% of retirement plan or IRA or Achieving a Better Life Experience (ABLE) account contributions totaling no more than $4,000 for married filing jointly, $2,000 for single filers. While the income thresholds are indexed to inflation, the credit itself is not.
In 2019, the maximum annual contribution for qualified plans, including SEP and Keogh plans, is $56,000 or 25% of your compensation, whichever is less; in 2020, the maximum contribution will rise to $57,000 or 25% of your compensation, whichever is less.
The estate tax exemption is both portable and indexed to inflation. The exemption is $11.40 million in 2019. The exemption will rise in 2020 to $11.58 million. The basic exclusion amount will remain at the higher level through 2025, though increasing by the chained CPI, a slower inflation measure. This is a per-spouse exclusion and it is portable, meaning that if one spouse passes away, the surviving spouse can claim the deceased’s exclusion, resulting in a total effective exclusion of $22.80 million in 2019 and $23.16 million in 2020. The large figures will prevent most families from having to pay estate taxes.
The maximum estate tax rate is 40%. The step-up basis rule applies when an inherited asset is sold: The capital gain resulting from the sale is calculated as the difference between the proceeds at the time of the sale transaction and the value of the assets at the time of the inheritance.
Executors have to report the fair value of the property included in the gross estate to both the IRS and to the heirs. Beneficiaries claiming a basis for inherited property above the reported value may be subject to a 20% penalty.
The annual gift tax exclusion in 2019 is $15,000 and $30,000 for consenting couples. (You will need to file Form 709.) These limits will be unchanged in 2020.
Individuals age 70½ and older are required to take a distribution from their retirement accounts by December 31, 2019. These accounts include 401(k) plans, 403(b) plans, 457(b) plans, traditional IRAs, SEP IRAs, SARSEP IRAs, SIMPLE IRAs and Roth 401(k) plans. RMDs from defined-contribution plans, such as 401(k) plans, can be postponed beyond age 70½ for those who are still working, contributing to a defined-contribution plan and own less than 5% of the company. Roth IRA plans are exempt from the RMD rules while the owner is alive.
If you turned 70½ in 2019, you have until April 1, 2020, to take your first RMD. You will need to take a second RMD no later than December 31, 2020, to satisfy that year’s distribution requirement.
According to the IRS, “Generally, an RMD is calculated for each account by dividing the prior December 31st balance of that IRA or retirement plan account by a life expectancy factor that the IRS publishes in tables in Publication 590-B, Distributions From Individual Retirement Arrangements (IRAs).”
The Tax Impact of Investing for and in Retirement
Various parts of the tax code govern how much can be saved for retirement, when withdrawals can be made and how much has to be withdrawn.
There are three big birthdays you should be aware of. At age 50, the maximum amount allowed to be contributed to retirement savings accounts increases (“catch-up contributions”). At age 59½, you can take withdrawals from all retirement accounts without incurring the 10% early withdrawal penalty. Finally, once you reach age 70½, you are no longer eligible to contribute to a traditional IRA and you must begin taking required minimum distributions (RMDs).
The tax code incentivizes savings for retirement. Workers can contribute up to $19,000 in 2019 (up to $19,500 in 2020) in a defined-contribution plan [e.g., a 401(k) plan]. A higher limit of $25,000 in 2019 ($26,000 in 2020) exists for workers age 50 or older. Taxpayers and spouses not covered by an employer retirement plan can contribute up to $6,000 ($7,000 for those age 50 or older) to a traditional IRA in 2019 and 2020, though the deductions are subject to income phaseouts. Contributions to a tax-deferred retirement savings account reduce adjusted gross income (and thereby your tax liability) as long as they are within the designated limits. Again, contributions to a traditional IRA can no longer be made starting at age 70½.
Contributions to Roth IRAs and Roth 401(k) plans are not tax-deductible. Like traditional IRAs, up to $6,000 ($7,000 for those age 50 or older) can be contributed to a Roth IRA in 2019 and 2020. The maximum contribution is subject to income phaseouts starting at $193,000 for married couples filing jointly and $122,000 for singles for 2019. (The phaseouts will increase to $196,000 and $124,000, respectively, in 2020.)
Contributions to IRAs and Roth IRAs for the 2019 tax year can be made as late as April 15, 2020. When making a contribution for the previous calendar year, ensure your broker registers the deposit correctly.
Withdrawals from retirement accounts are considered to be taxable income unless taken from a Roth IRA, a Roth 401(k) or similar types of accounts. RMDs are required from most retirement accounts starting at age 70½. (The first RMD can be taken as late as April 1 of the calendar year following the year you turned age 70½, though the second RMD must be taken by December 31 of that same year.) The percentage of retirement savings subject to the RMD increases every year. Roth IRAs are exempt from RMDs, but Roth 401(k) plan savings are not. [A Roth 401(k) can be rolled to a Roth IRA.] Those who are still working, contributing to an employer-sponsored retirement plan and own less than 5% of the company they work for can delay the first RMD from a defined-contribution plan until April of the year they retire.
A discussion of all the tax aspects of investing for and in retirement is beyond the scope of this guide. Those seeking greater detail should read IRS Publications 590-A and -B on Individual Retirement Arrangements.
The TCJA set the maximum child tax at $2,000 through 2025. In 2019, the credit is refundable up to $1,400. The refundable portion is indexed to inflation but will remain at $1,400 in 2020.
The “kiddie tax” applies to children up to age 18 and could apply to children up to age 23—depending on how much earned income they have and whether or not they are full-time students.
Under the kiddie tax rules, children with 2019 investment income above a certain amount may have part or all of their investment income taxed at trust tax rates through the end of 2025.
The kiddie tax applies if the child is age 17 or younger by the end of the year. In 2019, the kiddie tax will apply if the child’s total investment income exceeds $2,200. The exemption is indexed to inflation but will remain at $2,200 in 2020.
In addition, the kiddie tax can apply to older children, depending on how much earned income they have and whether or not they are full-time students.
Donations of clothing and other personal items must be in “good condition” or better in order to be deducted. Form 8283 must be filled out if your total deduction for all noncash contributions exceeds $500.
In addition, charitable contributions of cash (regardless of the amount) to any qualified charity must be supported by a dated bank record (such as a cancelled check) or a dated receipt from the charity that includes the name of the charity and date and amount of contribution.
Those age 70½ or older can distribute up to $100,000 from their traditional IRA to qualified charities in 2019 and 2020. The provision allowing qualified charitable distributions (QCDs) was permanently reinstated late in 2015; the cap on donations is not indexed to inflation. QCDs reduce required minimum distributions. See “The Tax Advantages of Qualified Charitable Distributions From IRAs” in the October 2016 AAII Journal for more information.
Taxpayers who itemize deductions can deduct (as a medical expense) the premiums they pay for Medicare Part B supplemental insurance and Medicare Part D prescription drug insurance. Premiums for voluntary coverage under Medicare Part A are only deductible by those over the age of 65 and not covered by Social Security.
Medicare Part B premiums are based on MAGI as reported on returns from two years ago. As such, the Medicare Part B premium will be $144.60 in 2020 for taxpayers who file married joint returns with 2018 MAGI of $174,00 or less and single filers with 2018 MAGI of $87,000 or less.
The floor for deducting medical expenses is back at 10% of adjusted gross income for 2019. It will remain at this level in 2020.
The phaseout of itemized deductions (the “Pease” limitation) was suspended for the years 2018 through 2025 by the TCJA.
Taxpayers who itemize deductions have the option of choosing between a deduction of sales taxes or income taxes when claiming a state and local tax deduction. Taxpayers cannot deduct both. A $10,000 limit ($5,000 for married filing separate returns) on state and local tax deductions is in effect through 2025. This cap is not indexed to inflation.
State and local governments are required to report interest paid on tax-exempt state and local bonds on Form 1099-INT, Interest Income. This amount must be shown on your tax return. While this income is generally exempt from federal income tax under the current tax law, it is used for determining how much of Social Security income is taxable. Income from private activity bond interest is included in alternative minimum tax calculations.
The 2019 minimum annual deductible for self-only coverage is $1,350; it is $2,700 for family coverage. These amounts are indexed for inflation and will rise to $1,400 and $2,800, respectively, in 2020. The 2019 maximum limits for annual deductible and other out-of-pocket expenses are $6,750 and $13,500, respectively. They will rise to $6,900 and $13,800, respectively, in 2020.
HSA contributions cannot exceed $3,500 for individual coverage and $7,000 for family HDHP coverage in 2019. In 2020, the maximum contributions will be $3,550 and $7,100 for individual and family coverage, respectively.
More on Health Savings Accounts
You may be able to deduct contributions to a Health Savings Account (HSA). These tax-free savings accounts were established under the Medicare Act of 2003 and can be used to pay for medical expenses incurred by you, your spouse or your dependents. They are used in conjunction with high-deductible health plans, where your basic health insurance does not cover first-dollar medical expenses.
HSAs may be established by anyone who is covered by an HSA-qualified “high-deductible health plan,” is not covered by any other health insurance and is not enrolled in Medicare. Qualified high-deductible health plans must have an annual deductible of at least $1,350 for self-coverage and $2,700 for family coverage in 2019. These amounts are indexed for inflation and will rise to $1,400 and $2,800, respectively, in 2020.
Tax-deductible contributions can be made to the HSA up to a maximum of $3,500 for self-coverage and $7,000 for families in 2019. In 2020, the maximum will increase to $3,550 for individual coverage and $7,100 for family coverage. If you are over age 55, you can also make a “catch-up” contribution to your account of up to $1,000 and still enjoy the same tax advantages.
Individuals can also make a one-time transfer from their IRA to an HSA, subject to the contribution limits applicable for the year of the transfer.
Contributions to HSAs can be made by you, your employer or both. You can fully deduct your own contributions to an HSA, even if you do not itemize, and contributions made by your employer are not included in your taxable income. The interest and investment earnings generated by the account are also not taxable while in the HSA.
Amounts distributed from the HSA are not taxable as long as they are used to pay for qualified medical expenses. They can be used to:
Amounts distributed that are not used to pay for qualified medical expenses will be taxable, plus a 20% penalty will be applied.
HSAs are similar to IRAs in that they are owned by individuals—you are not dependent on a particular employer to enjoy the advantages of an HSA. And if you change jobs, the HSA goes with you.
What if you already have an existing medical savings account (MSA)? In that case, you can either retain it or roll the amount over into a new HSA.
See also “Investor Professor: Health Savings Accounts” in the July 2016 AAII Journal and read IRS Publication 969, available at www.irs.gov.
The maximum Hope Scholarship Credit (the American Opportunity education credit) of $2,500 per year for the first four years of post-secondary education for tuition and related expenses (including books) was made permanent by the Consolidated Appropriations Act of 2016. As such, this credit can be claimed in both 2019 and 2020.
The Lifetime Learning Credit can be claimed for education expenses beyond the fourth year of post-secondary education and for non-degree courses intended to improve job skills. The maximum credit is $2,000 annually and is subject to income phaseouts.
You can make nondeductible contributions to qualified tuition plans, also known as section 529 plans. (However, the contributions may be deductible from your state income tax, depending on where you live.) These accounts, offered by states or their designees, are maintained solely for the qualified higher education expenses of a beneficiary. Distributions are tax-free, provided that the distributions are used to pay qualified expenses.
The ATRA made the $2,000 per beneficiary contribution limit to a Coverdell Education Savings Account permanent. The contributions are not deductible, but they grow tax-free in the IRA.
Coverdell accounts may be used to fund qualified elementary, secondary and higher education expenses. However, the amount that can be contributed is limited for higher-income taxpayers and the phaseouts are not adjusted for inflation.
Though the ATRA and the Consolidated Appropriations Act of 2016 provided clarity in terms of current legislation, the TCJA had a much bigger and broader impact on the tax code. Not only did the tax brackets for individuals change, but so did many deductions and exemptions.
Listed below are traditional tax planning strategies that can help keep your tax bill down. It is important, however, to keep in mind that your goals and risk tolerance, not just the income tax impact of an investment, should drive your investment decisions.
You have the option of converting all or part of your traditional IRA into a Roth IRA, regardless of your adjusted gross income under existing law. Roth IRAs can provide certain advantages: The converted assets can be withdrawn tax-free at any time and future earnings also tax-free (with some limitations). Withdrawals do not impact how much of Social Security benefits are taxed nor do they count as income for determining Medicare premiums. Additionally, Roth IRA owners are not required to take any minimum distributions in retirement. The downsides, however, are that the conversion amount is taxable in the year it occurs, it can increase the amount of Social Security benefits taxed in the year of conversion and can increase Medicare premiums two years out.
While the benefits of a Roth IRA conversion could be considerable, taxpayers must carefully weigh the upfront tax costs against the long-term tax advantages. For more on this, see “Retirement Planning Strategies Following the 2017 Tax Act” and “Social Security and Medicare Can Raise Retirees’ Tax Rates” by William Reichenstein and William Meyer in the March 2018 and April 2018 AAII Journal, respectively. You may also want to consult a tax professional.
Conversions can no longer be undone (a “recharacterization”); this was ended by the TCJA.
You cannot convert required minimum distributions from your traditional IRA for a particular year (including the calendar year in which you reach age 70½) to a Roth IRA. IRS Publication 590-A explains the rules for Roth IRA conversions and Publication 590-B covers the rules for RMDs.
Deferring income that is taxed at higher ordinary tax rates makes sense. Most taxpayers will pay long-term
capital gains tax rates of 0% or 15%. For married couples filing jointly with income above $488,850 and single filers with income above $434,550 in 2019, the long-term capital gains rate is 20%. In 2020, the 20% long-term capital gains tax rate will apply to married couples filing jointly and single filers with incomes above $496,600 and $441,450, respectively. Short-term capital gains, in contrast, are taxed at ordinary income tax rates of up to 37% in 2019 and 2020. The 3.8% NII surtax applies to taxpayers with income above the $250,000/$200,000 thresholds. This tax applies to both short- and long-term capital gains, as well as taxable interest, dividends, non-qualified annuities, rents and royalties and passive income from partnerships. The NII surtax is not indexed to inflation, and the $250,000/$200,000 thresholds are effective for both 2019 and 2020.
Similar rules apply to qualified dividends. For married couples filing jointly with income above $488,850 and single filers with income above $434,550 in 2019, dividends are taxed at 20%. In 2020, the 20% qualified dividend tax rate will apply to married couples filing jointly and single filers with incomes above $496,600 and $441,450, respectively.
Though tax considerations should never be the primary reason for selling a security, if you have large positions in either gifted or inherited stocks, or stocks received from a sale of a business, you should consider whether it makes sense to sell shares over a period of time to take advantage of the long-term capital gains rates and use the proceeds from selling the stock to diversify your portfolio.
While tax considerations should not drive your investment decision, you can take advantage of losses in holdings that you would prefer to either sell or reduce from an investment standpoint.
Capital losses first reduce capital gains: long-term losses reduce long-term gains first, and short-term losses reduce short-term gains first. Any long-term losses left over reduce short-term gains, and vice versa. If you still have losses remaining after offsetting capital gains, you can reduce your “ordinary” income by up to $3,000. Losses not used this year can be carried forward to future years until they are used up. See “Capital Pains: Rules for Capital Losses” by Julian Block in the September 2010 AAII Journal.
When planning, make sure you don’t run afoul of the wash-sale rules. If you sell an investment at a loss and then acquire a substantially identical security during the 30-day period prior to or the 30-day period following the sale, the loss will be disallowed. If your loss is disallowed by the wash-sale rule, you can increase the cost basis of the new position of the substantially identical security by the amount of the disallowed loss. The holding period for the new position is also adjusted to include the holding period of the position sold at the disallowed loss. You cannot adjust the cost basis or holding period if you acquire the investment in an IRA or Roth IRA, however. For more information, see “Keeping Transactions Clean From the Wash-Sale Rules” by R. Kevin Trout in the December 2014 AAII Journal.
In order to qualify for the reduced 15% (20% for higher earners) tax rate on qualified dividends for common and preferred stocks, a holding period must be satisfied. Specifically, common stocks must be owned for more than 60 days during the 121-day period that begins 60 days before the ex-dividend date. (The holding period is more than 90 days out of a 181-day period for preferred stocks with dividends attributable to periods aggregating more than 366 days.) The ex-dividend date is generally one trading day prior to the record date.
Not all dividends are qualified. Qualified dividends are paid by common and preferred stocks. Real estate investment trust (REIT) distributions and master limited partnership (MLP) distributions do not qualify for the discounted taxed rate. Contact the investor relations department of the specific company if you have questions about the tax treatment.
Selecting tax-aware managers of mutual funds may be important to maximizing your aftertax rate of return in your taxable investment portfolio.
You may choose when to sell specific shares of the fund and may, therefore, create long-term versus short-term capital gains, as long as you notify the fund family or your broker in writing with specific instructions. But you don’t control the investments within the fund.
Should an equity manager fail to extend the holding period on a stock, it could cost you as much as 17.0% of your gain (37.0% ordinary rate for short-term capital gains versus the 20% long-term capital gains rate) between now and 2025.
Some mutual fund distributions can be treated as qualified dividends and therefore eligible for the reduced tax rate, while others will not qualify. Dividends paid by stocks held by the fund and passed through to the shareholder are eligible for the qualified dividend tax treatment. However, capital distributions and interest from bonds are not. These payments are reported on Form 1099, which specifies the type of distribution.
You can read more on mutual fund distributions in the 2019 Personal Investments Guide.
Interest from tax-free municipal bonds is generally exempt from federal income taxes, unlike the interest from taxable bonds, which is taxed as income. Like any bond, credit quality matters, as you want to ensure that the issuer will not default. Changing yields can also alter the aftertax yield advantage, making municipal bonds more or less attractive to taxable bonds.
Additionally, private-activity bonds (a type of tax-free bond) could increase your exposure to the alternative minimum tax since their interest income is taxable for purposes of the alternative minimum tax. There are exceptions, including qualified 501(c)(3) bonds, and New York Liberty bonds. Furthermore, the interest on qualified bonds issued in 2009 and 2010 is not subject to the alternative minimum tax. Check with the bond issuer to find out the bond’s tax status.
You should review your bond and money market accounts to make sure that you are earning the highest aftertax return. But don’t forget to consider the state tax implications of switching from tax-free to taxable bonds before making any final portfolio decisions.
Increasing retirement savings makes sense from a financial planning standpoint and, depending on your adjusted income, may reduce your tax bill. You have until April 15, 2020, to make an IRA contribution for the 2019 tax year. See “The Tax Impact of Investing for and in Retirement” box for yearly contribution limits to various types of retirement plans.
The spread between capital gains and ordinary income rates has important implications with respect to your asset allocation between taxable and tax-deferred (retirement) accounts.
For example, from a tax perspective, holding individual stocks in tax-deferred accounts and bonds in taxable accounts could be expensive because the long-term gains resulting from stocks held in tax-deferred plans such as IRAs or 401(k) plans will be taxed at ordinary rates when taken as a distribution. By reversing that structure, taxable bonds and other tax-inefficient assets will be shielded from taxation in the deferred accounts, while equities will enjoy the reduced rates for capital gains in personal accounts.
Tax-free municipal bonds should remain outside of retirement accounts. Individuals should also consider the cost of commissions and taxes, current cash flow needs, and the 0.9% additional Medicare tax and 3.8% NII surtax before making any investment moves between taxable and tax-deferred accounts.
If you are receiving Social Security benefits, you may have to pay taxes on them if your combined income (primarily your adjusted gross income plus any tax-exempt interest income plus half of your Social Security benefits) exceeds certain levels.
To protect your benefits, watch the amount of interest you receive from municipal bonds, since this amount is included in your modified adjusted gross income when determining the Social Security benefit taxability. In addition, you may want to delay discretionary taxable distributions from a retirement plan or IRA.
It is important to remember that taxes should not be the primary driver of your investing decisions. Taxes do, however, play a role in wealth management. As the tax code continues to evolve, everyone should consider how the changes directly affect their overall tax and investment strategies.
Where’s My Money? Tracking Your Refund 24/7 
If you are expecting a refund on your 2019 income tax, you can check on its status if it has been at least four weeks since the date you filed your return by mail, or 24 hours if you filed electronically. You will need to supply the following information: your Social Security number or IRS Individual Taxpayer Identification number, your filing status and the exact whole-dollar refund amount as it is shown on your return.
You can check the status of your refund in two ways:
If you are unable to get information on your refund through either of these two automated services, you can call the IRS for assistance at 800-829-1040.
The IRS website also allows you to start a trace for lost or missing refund checks, or to notify the IRS of an address change when refund checks go undelivered. Taxpayers can avoid undelivered refund checks by having refunds deposited directly into a personal checking or savings account. This option is available for both paper and electronically filed returns.
At the end of each year, you should take the time to assess your tax situation. Doing so will give you the opportunity to shift certain items around, should that be beneficial in terms of your tax liability. Taking a few initial steps now and using year-end planning strategies can result in significant tax savings.
Here are the basic steps you should take to help start your personal tax planning:
To minimize your taxes, consider both short-term and long-term tax planning issues and strategies. Starting early will give you extra time to obtain additional information about items that concern you and to investigate additional ideas for tax savings or deferral.
Make sure you determine your 2020 tax liability as early as possible, as well as the due dates for paying those taxes (including the self-employment tax and the AMT), so that you avoid underpayment penalties.
Federal tax law requires the payment of income taxes throughout the year as you earn your income. This obligation may be met through withholding, quarterly estimated tax payments or both. If you do not meet this obligation, you may be assessed an underpayment penalty.
If your total tax due minus the amount you had withheld is less than 10% of your total tax due, you will not be assessed an underpayment penalty. The disadvantage of overpaying throughout the year, though, is that you are in effect making an interest-free loan to the government. However, the underpayment penalty can be high, and it is calculated as interest on the underpaid balance until it is paid, or until the regular filing date for the final tax return, whichever is earlier.
You can avoid underpayment tax penalties by adopting one of the safe harbor rules. The basic rule is to pay the required amount by the end of the year through withholding and quarterly estimated payments. The required amount will be one of the following, depending on your individual situation:
Penalties are based on any underpayment, which is the difference between the lowest amount required to be paid by each quarterly payment date and the amount actually paid by that date. The annual required amount, based on either of the first two alternatives, is paid in equal installments. In the case of the third method, which is based on annualized income, the amount due each quarter is based on actual income received for each installment period. The third method is typically more beneficial if you do not earn income evenly throughout the year (e.g., you operate a seasonal business) or had an unexpected increase in income because it allows for lower required payments in the early quarters.
Income tax payments made through withholding from your paycheck (or from your pension or other payments) are given special treatment. The IRS treats income tax that is withheld as having been paid equally throughout the year (unless you prefer to use actual payment dates). This lets you make up for underpaid amounts retroactively because amounts withheld late in the year may be used to increase the amounts paid in earlier quarters.
State and Local Rules: Many states have underpayment rules that vary from the federal requirements.
You have opportunities to reduce your taxes if you can control the timing of either your income or expenses. However, it is important to make sure you understand whether you may be subject to the AMT before adopting these strategies. Though the TCJA retained the alternative minimum tax, it will not apply for 2020 incomes below $1,036,800 for married couples filing joint returns and $518,400 for others.
AMT: An Unpleasant Surprise
Are you subject to the alternative minimum tax? This tax comes as a surprise to many taxpayers. You may be subject to this tax, especially if any of the following criteria apply to your situation:
The alternative minimum tax is calculated by first determining the tentative minimum tax. The 2019 minimum tax for married couples filing joint returns and singles is 26% of the first $194,800 of alternative minimum taxable income in excess of the exemption amount, plus 28% of any additional alternative minimum taxable income. A 26%/28% threshold of $97,400 exists for married filing separately. In 2020, the 28% tax rate applies to income above $197,900 for married couples filing joint returns and singles and applies to income above $98,950 for married filing separately. The exemption phaseout levels for 2019 are $1,020,600 for married couples filing joint returns and $510,300 for others. They will rise to $1,036,800 and $518,400, respectively, in 2020. However, for alternative minimum tax purposes, dividends and capital gains will be taxed under the same rules as those used for regular tax calculations. The alternative minimum tax is the excess of the tentative minimum tax above the regular tax calculated.
Alternative minimum taxable income adds back certain preference items to regular taxable income—including state income taxes, real estate taxes and foreign income taxes—and can cause the alternative minimum tax to be larger than the regular tax.
In addition, although the tax rate on capital gains and dividend income is the same for both the regular tax and the alternative minimum tax, the disparity in rates between the alternative minimum tax and the regular tax may result in a higher effective rate on all income, including capital gains and dividends.
To find out if you may be subject to the AMT, use tax preparation software or refer to the Alternative Minimum Tax (AMT) section in the Form 1040 Instructions at www.irs.gov.
Income
Your income is generally taxed in the year of receipt, so having the ability to control when you receive it affords a strategic tax planning opportunity. Deferring income until a later year will, in most cases, delay the payment of tax. You cannot defer taxation by merely delaying receipt of the income if the funds are available to you and the time of payment is subject to your unrestricted discretion. Any decision to defer income must be weighed with the lost time value of the money and other risks that could alter or forfeit your right to the income.
The timing of bonuses, recognition of capital gains from the sale of stocks, and the exercise of non-qualified stock options are all events that can easily be delayed into a subsequent year.
Consider the deferral of compensation through the use of various retirement plans and deferred-compensation arrangements. If you operate a business or collect rental income and report that income on the cash receipts and disbursements method, you have an opportunity to delay or accelerate the billing to your customers or tenants and determine the timing of the related income.
Deductions
You can reduce taxes by controlling the payment of deductible expenses. If paid by December 31, you may deduct certain expenses that are due the following year on your current year tax return. (Property taxes prepaid in the current year can be deducted if assessed in the current calendar year and if the $10,000 limit on state and local taxes has not been reached.) This strategy helps when you have a higher tax liability in the current year than you expect to have in the coming year. Again, you must balance this decision with the time value of money and other inherent risks.
For example, if you pay a deductible expense in December 2019 instead of April 2020, you reduce your 2019 tax instead of your 2020 tax, but you also lose the use of your money for three-and-one-half months. Generally, this will be to your advantage, unless you have an alternative use for the funds that will produce a very high return in that three-and-one-half-month period. You must decide whether the cash used to pay the expense early should be used for something more urgent or more valuable than the accelerated tax benefit.
For those who will pay 2020 estimated taxes based on their 2019 tax liability, reducing your 2019 taxes has another advantage: Your 2020 estimated tax payments may be smaller.
State Taxes
If accelerating deductions makes sense for you and you choose to claim a deduction on your state and local income taxes, you may want to prepay the balance on your estimated state tax liability in December 2019, rather than waiting until 2020, if the taxes were assessed in 2019. This secures that deduction on your 2019 tax return, even though the payment might not be required by the state until January 15, 2020, or April 15, 2020. The deductibility of these taxes is subject to a $10,000 cap on state and local taxes in 2019. The cap is not indexed to inflation and will remain at $10,000 per year through 2025.
Charitable Contributions
If you are planning on making a gift to a charity in 2020, consider making the gift in 2019 to accelerate the tax benefit of the contribution if you have enough deductions to exceed the $24,400/$12,200 standard deduction. However, it is important to note that certain limitations exist with respect to deductions for charitable contributions.
You should also consider the benefits of gifting appreciated stock to a charity. If you donate long-term appreciated stock directly to the charity, you get a deduction for the full fair market value of the stock, whereas if you sell the stock first and donate cash, you only get a deduction for the aftertax cash donated. (If you have an unrealized loss in the stock, however, it might be more beneficial from a tax standpoint to sell the stock and then donate the cash proceeds. Doing so would give you deductions for both the capital loss and the charitable donation.)
When making a gift to a charity, you must have an appropriate record of the gift in order to properly support the deduction.
In addition, cash contributions of any amount must be supported by a written record, either in the form of a bank record (for example, a cancelled check) or a written receipt from the charity. The record must include the name of the charity, the date and the amount of the contribution.
The higher standard deductions under the TCJA raised the threshold for deducting donations. As such, you may want to bunch donations in a particular year rather than making them over two or more separate years.
Prepaid Interest
A cash basis taxpayer may not deduct prepaid interest before the tax year to which the interest relates. However, there is some flexibility to prepay year-end interest that is due early in the following year.
For example, if a mortgage payment is due on January 10, a taxpayer can accelerate the deduction of the portion of the interest relating to the period up to January 1 by mailing the check in December.
The most significant interest deductions currently available are for home mortgage interest and for investment interest expense to the extent of current-year investment income. Interest paid in relation to investments that earn a tax-free return is not deductible.
Medical Expenses
If the timing of certain medical and dental expenditures is flexible and your overall medical expenses are high in the current year, you may want to accelerate the timing of these expenses.
Because unreimbursed medical expenses are only deductible to the extent that they exceed 10% of adjusted gross income in 2019, it is best from a tax standpoint to incur expenses—such as replacement eyeglasses or contact lenses, elective surgery, dental work and routine physical examinations—in a year in which you have already gone over (or in which the added expenses would take you over) the 10% threshold.
Miscellaneous Itemized Deductions
Miscellaneous itemized deductions exceeding 2% of adjusted gross income can no longer be claimed as of January 1, 2018. The suspension of the ability to claim such deductions lasts through 2025.
This category is large but includes:
Uninsured Personal Casualties
Uninsured personal casualties can be deducted only if they are attributable to a federally declared disaster and exceed 10% of adjusted gross income. Losses to theft are no longer deductible. The rule is in effect from 2018 through 2025.
The alternative minimum tax (AMT) was originally designed to ensure that everyone would pay their fair share of income taxes. The measure has since evolved into a separate tax regime that required a permanent fix in the ATRA to prevent it from ensnaring millions of Americans.
The wisdom of conventional tax planning advice to defer income and accelerate certain types of deductions may not hold true if an individual expects to be subject to the AMT. Accordingly, during the tax planning process, it is critical that you determine whether you are subject to the AMT in both the current year and the following year.
If you are continuously subject to the AMT, avoid investing in private-activity (municipal) bonds. Income from these bonds is taxable for AMT purposes. [There are exceptions, including qualified 501(c)(3) bonds and New York Liberty bonds. Also, the interest on qualified bonds issued in 2009 and 2010 is not subject to the AMT. Check with the bond issuer for the bond’s tax status.] Furthermore, you should be aware that unusual combinations of income and deductions might require AMT planning that runs contrary to conventional tax-planning advice.
Although the exercise of an incentive stock option (ISO) does not give rise to regular taxable income for the employee, the difference between the exercise price and the market price of a stock must be recognized for AMT purposes for the year in which the option is exercised. Accordingly, the exercise of incentive stock options with a large bargain element often causes a tax liability under the AMT regime.
The AMT arena is extremely complex, so generalizations are difficult to make. If you think you may be subject to the AMT, you should consult a tax professional to determine how best to minimize your exposure to it.
As stated previously, the TCJA retains the alternative minimum tax, though with higher exemptions and income limits through 2025.
Year-end planning from an estate planning perspective typically involves ensuring that “annual exclusion” gifts are completed by the end of a calendar year.
Under the federal gift tax system, each donor is permitted to make non-taxable gifts of a certain amount each year to any donee. These gifts are called “annual exclusion” gifts and do not count against the donor’s lifetime gifts exemption. The annual gift tax exclusion level is $15,000 for 2019 and 2020. To the extent that it is not used, the annual exclusion evaporates at the end of each calendar year.
Annual transfers that take advantage of this exclusion can both diminish the donor’s estate tax liability and improve the lives of the recipients. These gifts can take many forms (such as cash, stocks, real estate, partnership interests) and can be given outright through Uniform Transfers to Minors accounts, and even through a trust—provided it contains special provisions designed to allow the gift to qualify for the annual exclusion.
Tax Strategies
Financial Planning
Financial Planning