Filing your taxes can get complicated depending on your unique circumstances, and not everyone has access to an accountant or other tax professional.
To help our readers get the tax help they need, I asked tax experts to answer several of our reader-submitted questions. These questions cover everything from paying taxes in retirement and whom you can claim as a dependent to whether or not you need to pay taxes on a gift.
Find out the answers to some of your most pressing tax questions.
As a 1099 truck driver, can I deduct my expenses for days on the road?
“The IRS allows for the deduction of ordinary and necessary business expenses,” said Eric Bronnenkant, CFP, CPA, head of tax at Betterment. “Common deductible expenses would include CDL fees, medical exams, gas, tolls, hotels, oil, repairs, tools, vehicle depreciation, interest on business loans and insurance.
“Meals are potentially tax-deductible if you are away from your tax home overnight — think, long-haul drivers,” he continued. “Meals are normally subject to a 50% limit. However, there is an 80% limit for interstate truck drivers working under Department of Transportation regulations. There is also another exception for meals in a restaurant for 2021 and 2022 that provides for a 100% deduction.
“Self-employed taxpayers may be eligible for an additional 20% deduction based upon QBI (qualified business income),” Bronnenkant said.
If I transfer money from stocks to an annuity instead of withdrawing the money to spend, will I have to pay capital gains taxes?
“An exchange of stock for an annuity contract is a taxable event,” Bronnenkant said. “If there are profits on the stock, they would be treated as a short- or long-term capital gain — short-term is one year or less and long-term is over one year.”
However, there is an exception, he noted.
“This transaction would be a nontaxable event if it occurred within a retirement plan like a 401(k) or IRA,” Bronnenkant said.
I inherited a beneficiary IRA when my mother passed in December 2021. She was already taking Required Minimum Distributions. Do I have to continue taking them?
According to Bronnenkant, the answer is yes.
“RMDs for non-spouse beneficiaries for deaths in 2020 or later are subject to the 10-year rule,” he said. “The initial understanding of the 10-year rule was that the account needed to be distributed by the end of the 10th year after death (but no distributions [were] required before that point). However, the IRS’ current interpretation is that annual distributions are also required in years one through nine.
“This flip flop has caused even more confusion in an area which already is confusing,” he noted.
We sold our house in Vermont in July 2022 and are now residents of Florida, a state with no income tax. We are retired teachers who taught in Vermont for 30 years and receive pensions from the State Teachers’ Retirement. Will we have to pay taxes to Vermont on that income?
According to Bronnenkant, you will not have to pay.
“Congress passed a law prohibiting a nonresident state from taxing retirement income,” he said. “Consequently, Vermont is prohibited from taxing the pension of a Florida resident — even if the pension was earned while working/living in Vermont.”
I mailed in my tax forms but I haven’t received any response. How can I track my tax refund?
“This is a particularly frustrating area and I completely empathize with your situation,” Bronnenkant said. “The IRS has been very slow to open mail and process paper-filed tax returns. A good way to track whether the IRS has processed a tax return — without spending time on hold calling — is to create an IRS online account and check the IRS refund tracker.”
I’m losing money on my rental home. Can I exclude the rental income from my taxes?
“The IRS only taxes net rental profits after deducting any expenses,” Bronnenkant said. “If the rental activity is operating at a loss, there are no taxes due to that activity. Whether losses can be used against other income depends on the level of participation in the activity.”
We were scheduled to take a trip in 2022. The day before departure, my spouse suffered a major medical emergency and ended up in the hospital. Are the losses — flight, rooms and car rental — deductible from our income tax for this year?
“The flight/rooms/car rental loss due to the inability to take a personal trip — even if due to a medical reason — is not tax-deductible,” Bronnenkant said.
Do I have to pay tax on a $20,000 loan from a family member?
“The borrowing of funds from family members and non-family members is not considered to be taxable income,” Bronnenkant said. “If funds are borrowed from family members at below-market interest rates, the amount of below-market interest may be taxable income to the lending family member, up to the borrower’s net investment income.”
I will be 75 years old this April and I still work. Will I pay the Social Security tax on my paycheck?
“Social Security taxes apply to wage income, regardless of age or whether collecting Social Security benefits,” Bronnenkant said. “The Social Security Administration states, ‘As long as you continue to work, even if you are receiving benefits, you will continue to pay Social Security taxes on your earnings. However, we will check your record every year to see whether the additional earnings you had will increase your monthly benefit. If there is an increase, we will send you a letter telling you of your new benefit amount.'”
Can you refile your 2021 taxes if you feel you did not receive the right refund amount?
“Amended tax returns can be filed for up to three years to claim a refund [using] Form 1040X,” Bronnenkant said.
In some circumstances, you may be able to file an amendment for returns that are over three years old.
“A refund can be claimed for up to seven years if due to worthless securities or bad debt,” Bronnenkant said.
I have an installment agreement with the IRS to pay back a tax debt. My husband and I are seniors approaching 70 years of age in a few months. Would the IRS consider age/retirement status if I were to request a waiver of all or part of this debt?
It’s possible, but it may be difficult to qualify, Bronnenkant said.
“An OIC — offer in compromise — is where the IRS will accept a lesser amount than the outstanding tax due. It is difficult to qualify for by its nature as the IRS wants to collect as much tax revenue as possible,” he said. “The IRS states, ‘Taxpayers who can fully pay the liabilities through an installment agreement or other means, generally won’t qualify for an OIC in most cases.'”
“However, if the IRS believes that there is (1) doubt to the liability, (2) doubt as to collectability or (3) effective tax administration, it is possible that they may accept less than the amount owed,” Bronnenkant said.
If you sell your house, do you need to buy another so you do not get taxed on the sale?
In short, the answer is no.
“The home sale exclusion of up to $250,000 [if your filing status is] single [or] $500,000 [if you file jointly] is allowed on the sale of a primary residence where the ownership and use test is met –this means that the home has been owned and lived in as a primary residence for at least two of the last five years,” Bronnenkant said. “The home sale exclusion has no requirement that another property be purchased.”
I’m married with five kids. My husband moved in with his mom in September to take care of her due to failing health. Our children go back and forth between households. Can we file separately, with me claiming three children and him two? Will we each get the child tax credits?
“In general, married couples filing a joint tax return will have a lower combined tax liability. The system is designed to encourage joint tax filing as couples are seen as one economic unit,” Bronnenkant said. “However, there are situations where filing separately may provide for a lower combined tax liability. I would suggest preparing taxes both jointly and separately before submitting to determine which option has a lower combined tax cost. Notably, the child tax credit starts being reduced at $200,000 for separate filers and $400,000 for joint filers.”
I received an inheritance from my father who lived and died in Illinois. I live in Wisconsin. I received a K-1 from the estate. Why do I have to pay taxes in a state that has no inheritance tax?
“K-1s are issued to the beneficiaries of an estate for their share of income from the estate — income typically from the decedent’s assets received after death commonly including interest, dividends and capital gains,” Bronnenkant said. “The K-1 has nothing to do with inheritance taxes.”
I am recently divorced. How will that affect my tax filing this year? And do I need to share a copy of the divorce papers with the IRS?
“When it comes to divorce and your taxes, the timing matters,” said Tom Wheelwright, CPA. “The IRS considers a couple married until a final divorce decree or separate maintenance is in place. If you had this on or before Dec. 31, 2022, you most likely will file as single for 2022.
“The exceptions to this are if you also remarried in the same year or if you qualify to file as head of household,” he continued. “If you are separated and want to file using the head of household status, you need to meet three criteria:
- Your spouse didn’t live in your home for the last six months of the year.
- You paid more than half the cost of keeping up your home for the year.
- Your home was the primary residence for your dependent children for more than half the year.
“If you work a W-2 job, you’ll want to update the W-4 that you have on file with your employer to ensure you have the proper withholdings for your new filing status.
“If you make alimony or other support payments, these aren’t deductible for divorces after 2019. If you are receiving these payments, this doesn’t count as taxable income.
“If you and your former spouse have minor children, you have a few additional things to consider come tax time. First, child support payments are not deductible for the payor and are not considered income to the recipient. Second, you will need to determine who gets to claim any children as dependents. Typically, this goes to the custodial parent. If you share custody, you will want to negotiate this as part of your divorce and custody agreement. It’s common to alternate years.
“You won’t need to share a copy of the divorce papers with the IRS with your initial tax filing. If the IRS questions your filing status, you will be asked to file Form 14824, which will include a list of specific documentation to provide.
“Tax issues can get complicated in a divorce, so it’s always best to work with a CPA who specializes in tax.”
I buy stocks to build wealth for my kids and grandkids. I never intend to sell any. Do I have to claim them on my income tax?
“No — you don’t pay taxes on assets you own, just money you earn,” Wheelwright said. “If you buy and hold these stocks, you won’t owe any tax. (Now, if you are buying and selling stocks within a taxable investment account, that’s a different story.)
“If your plan is to pass these stocks down to your heirs when you die, it’s important to work with your tax advisor and an estate planning lawyer,” he continued. “Creating a strong estate plan is one of the best gifts you can give to your family.”
Is the money that l got for selling my apartment in another country going to be taxable? The money is now in my U.S. bank account.
“If you profit off of the sale of a property, whether it is located in the United States or another country, you need to report that income,” said Ferencz Kaszoni, founder of Income Tax. “This is the case for any country in which you earn income. The United States taxes you on your total income, not just the income earned within its borders, so if you own a home or property in another country and sell it, make sure to include that profit in your tax report.”
If you don’t have medical insurance, can this affect your tax return?
“There is no longer a federal mandate to have health insurance and you do not need to report health insurance exemptions on your tax return,” Kaszoni said. “However, if you purchase health insurance through the marketplace and receive Form 1095-A, you will need to report this in order to claim the Premium Tax Credit.”
Can I file taxes this year if I haven’t filed the previous two years due to financial difficulties?
“If you haven’t filed your prior year’s taxes, do so immediately, regardless of the reason,” said Giuseppa Maceri, a CPA with Ageras. “I suggest putting the current year’s taxes on extension — but still paying an estimated tax payment — to ensure you have all files current. Note that you might incur a failure-to-file penalty unless you have reasonable cause for your failure to file timely. Tax not paid in full by the original due date of the return — regardless of extensions of time to file — may also result in the failure-to-pay penalty. Mark your calendars, and stay current.”
My brother is living with me and is helping with utilities — he contributes less than $100 per month. Do I need to consider this as income?
“Typically, any income received for renting your home would be considered income,” Maceri said. “In this situation, it appears that the tenant (your brother) is paying less than the fair market value for the home. You would not need to claim the income. However, you cannot claim any rental expenses or rental loss on your taxes. The government considers this situation to be a ‘cost-sharing arrangement.’ If you mistakenly claim deductions, you can be fined by the IRS.”
I’m a 77-year-old widower and I am retired. I have a 23-year-old granddaughter and a 54-year-old son living with me. They both work and file their taxes as single. I have filed as single since my husband passed in 2014. Since I own my home, pay all expenses involved and allow them to live with me and do not charge them any rent, can I file as head of household on my return?
“Over the past few years, we have seen an increase in the head of household filing status,” Maceri said. “Many young adults are moving back home, partly due to the poor economy and the job market, but also for security purposes.
“To qualify as a head of household filing status, you must meet the following requirements:
- You are unmarried
- You paid more than half the cost of keeping up a home for the year.
- A qualifying person lived with you in the home for more than half the year. However, if the qualifying person is your dependent parent, your dependent parent doesn’t have to live with you.
“In this situation, you would qualify as head of household.”
My wife has natural gas rights for which she receives royalties, and I have no income personally. We are filing jointly. How do I report this income?
“You and your spouse can file a joint return and must include all your income,” Maceri said. “It doesn’t matter who earns the income. Married filing separately is also an option if there’s a significant difference between each income, and the lower-paid spouse is eligible for substantial itemizable deductions.”
My son turns 19 this year. He is a full-time student who lived with me all year. He worked and made over $13,000 in wages, but I’ve supported him and paid more than half of his living expenses. Can I claim him as a dependent? Does he have to file his own taxes? And should he claim his dependents as 0?
“Yes, you can claim him as a dependent,” said Shiloh Johnson, CPA, CEO and founder of ComplYant. “No, he doesn’t have to file his own taxes. Because the son lived with you the entire year, that means he is still a dependent. He needed you for a majority of his care — living conditions, medical, food, etc. He paid for some of his expenses, but is still under the threshold so you can claim him — but you don’t need to include his income.”
I received a lottery ticket as a gift and won $5,000 Do I owe taxes on it?
“The ticket was the gift, not the winnings,” Johnson said. “The ticket was probably a couple of dollars, but the winnings are separate. The winnings income is taxable.”
Can I write off all of the lottery tickets I have purchased over the year, whether they were winners or losers?
“Yes, but you will need to include the income you won for all the winners,” Johnson said. “You can also write off what you lost for all the losers, but you do have to include all the winnings.”
How much tax will my children have to pay on my mutual funds money when I die?
“That depends on whether or not the funds are inside of a living trust,” Johnson said. “If they are not inside of a living trust, it will go into probate. If they are inside of a living trust, they will not. The extent of that taxability differs on where you are in the world and in the country, so I suggest contacting an accountant directly.”
If I have a trust fund set up by my parents and use it to make monthly house payments, is that considered taxable income?
“It depends on how the trust fund was funded,” Johnson said. “If these are funds that went into the account as a gift when you were a child, then odds are your parents paid some kind of gift tax for gifting it to you. If these are investment accounts that are earning interest over time and you are drawing up the money on interest, then yes, that interest is income. I suggest contacting an accountant directly to get more personalized advice.”
I received three 1099-INT from my banks: one for 49 cents, one for $20.98 interest from Treasury obligations and the other for $100.04. Do I need to add them to my taxes? In the past, the banks never sent me a 1099-INT if it was for less than a certain amount.
“You should report any income on any 1099 forms that have been sent to you, regardless of the amount,” Johnson said. “If they’ve been sent to you, they’ve also been sent to the IRS, which means that the IRS is expecting you to record this income. Even though it’s immaterial, you definitely don’t want to mess up here or cause any space for audit.”
If you do a side job for someone and make over $1,000 but they don’t file a 1099, is that money taxable?
“Technically, all income you receive for any work that you do is taxable regardless of how that money was or was not reported to the IRS,” Johnson said. “You should not do anything with your income based on what someone else did or didn’t do. They may not tax the person who paid you, or the person may not get audited and get out of it, but it’s a bad habit to try and finagle what you do based on what the government or the issuer did or didn’t do.
“You as the business owner or the individual who is receiving the money should always set your sights on doing the right thing, even if the other side didn’t,” she continued. “If the other side didn’t do the right thing and they get audited, and then the IRS comes to you and you didn’t do the right thing, you’re going to pay the price too. It’s always good measure to do the right thing. Include any money you receive, even if it’s immaterial.
“Small amounts mean you’re probably not going to pay much tax anyway, which means it’s not a huge deal, so it’s probably better to report it. Make sure you keep yourself above water, even if other people are drowning.”
In 2022 we sold our long-time house and bought a much lower-priced condo. How do we report this on our taxes? The capital gain on the house sale was less than $500,000.
“If you used your home as a principal residence for at least two of the five years ending on the date of the sale, the gain — or a portion of the gain — might not be taxable,” said Nadia Rodriguez, CPA and senior tax analyst programmer at Intuit. “However, the sale of your home must still be reported on your tax return for the year of the sale. You can exclude up to $250,000 ($500,000 for certain joint filers) from the gain of the sale of your principal residence.
“For your newly purchased condo, document the cost and improvements made to your home,” she continued. “This will ensure the cost of your home includes all improvements made throughout the years and will save you time when and if you sell your home in the future.”
My friend’s two daughters lived with me last year for a total of 14 months. Their mother is homeless. Can I claim them on my taxes?
“A dependent can be a qualifying child or a qualifying relative,” Rodriguez said. “One of the ‘five tests’ for a child to qualify as a qualifying child is the relationship test. For the relationship test, the child must have been your son, daughter, stepchild, adoptive child, etc. Since the daughters of your friend fail to meet the relationship test for a qualifying child, the next step is to look at the ‘four tests’ for the child to qualify as a qualifying relative:
- Not a qualifying child test: The child must not have been the qualifying child of another taxpayer. Therefore, if your friend has failed to meet one or more of the ‘five tests’ to claim her daughters as a qualifying child, you will meet this test.
- Member of household or relationship test: The child must have lived with you all year as a member of your household.
- Gross income test: The child’s gross income for the year must be less than $4,400.
- Support test: You must have provided more than half the child’s total support during the calendar year.”
How can I find someone to help with my taxes that I can afford?
“Free tax preparation advice and guidance may be available through various organizations, such as AARP Foundation Tax-Aide, or through your state’s tax agency,” said Emily G. Irwin, senior director of advice at Wells Fargo Wealth & Investment Management. “For certain qualifying individuals, the Internal Revenue Service also offers free basic tax return preparation through its Volunteer Income Tax Assistance (VITA) program and Tax Counseling for the Elderly (TCE) program. Generally, these programs require you to be a person with a disability, speak limited or no English, or have an annual income of less than $60,000. TCE focuses on individuals age 60 or older.”
I have a newborn child who was born on Dec. 21, 2022. Does he qualify me for a tax credit for the 2022 tax year?
“Congratulations! Your bundle of joy arrived in time for you to claim your newborn as a dependent for the 2022 tax year,” Irwin said. “To qualify, a child may be born anytime during the tax year until 11:59 p.m. on Dec. 31.”
I sold my house in 2022 and will begin construction of my new home in the first quarter of this year. I will use money from the sold house to build my new home. What and how do I need to declare on my 2022 tax form?
“If you owned and lived in the home you sold for a total of two of the five years before the sale, then up to $250,000 of profit is tax-free — or up to $500,000 if you are married and file a joint return,” said Mark Jaeger, VP of tax operations at TaxAct. “In that case, you wouldn’t need to report any money from the sale of your home on your 2022 return. But if your profit exceeds the $250,000 or $500,000 limit, the excess likely needs to be reported as a capital gain on Schedule D of your 2022 return.”
My employer didn’t take any federal taxes from my paycheck in 2022 even though my W-4 was correct. Do I need to file additional forms to explain this to the IRS?
“Unfortunately, this is a tough situation for you as you will need to pay the amount of tax your employer should have withheld during the year as unpaid taxes when you file your return,” Jaeger said. “You do not need to alert the IRS of that, however. Simply file your return as normal and be prepared to pay the amount owed. The IRS does offer tax payment plans if that is of interest. You should also reach out to your employer to ensure the correct amount of taxes is withheld going forward.”
I’m ashamed to say I haven’t filed taxes in over 10 years because of my ignorance, among other factors. I have all my W-2s for those years missed. Can I still file for all those years missed? Would I still get those refunds? Is it possible I’d get penalized for not doing them?
“The silver lining here is that you’re now aware that you need to file, so that’s a step in the right direction for your future,” Jaeger said. “The first step is to determine whether the IRS filed a Substitution for Return (SFR) on your behalf, as you are liable for that if it’s been completed. When an SFR is filed, it may leave off some deductions or exemptions that belong to you for the respective tax year and result in a higher tax bill. However, you don’t necessarily have to accept that outcome. You can go back and refile those tax years, including any appropriate deductions and exemptions to decrease the tax owed and reduce any interest and penalties.
“If the IRS has not filed an SFR for any of those missed years, it is best for you to file an old return before a demand is made,” he continued. “There is no time limit for submitting a previously unfiled return, but if you still want to claim a refund, you only have up to three years from the return’s due date.”
My wife and I each received a 1099 as loss payees from the Camp Fire, which destroyed our home in Paradise, California, in 2018. The payment was made by the trust that was representing PG&E. Should we be taxed on those payments?
“No, generally, settlement awards are not considered taxable income,” Jaeger said.
My husband died and his IRA was rolled over to one open in my name. Do I report the RMD distribution as my income?
“Yes, being that the money from the RMD went directly to you and not the estate, it is considered taxable income on your return,” Jaeger said.
How do I account for my California gasoline stimulus payment on my taxes?
“That money is not taxable on your California state return or your 2022 federal return,” Jaeger said.
I am a widow and I live alone. My total yearly income is $31,000. It comes from Social Security widow’s benefits and VA survivor benefits. Even though both benefits are nontaxable, will I now have to pay taxes just because my total yearly income exceeds $25,000?
“It’s definitely possible,” Jaeger said. “If your modified adjusted gross income is over $25,000, then yes, you likely need to pay taxes on that amount.”
I received money from my divorce settlement. It was from a 401(k) and I took the complete amount out. Will I have to pay a penalty?
“401(k) and other retirement transfers pursuant to a divorce are generally non-taxable,” Jaeger said. “However, once the money is transferred, regular tax rules apply to payouts or withdrawals from the account.”
Are caregiver expenses deductible as medical expenses?
“Yes, costs related to taking care of an elderly parent, relative or even a qualified friend are eligible for tax deductions,” Jaeger said.
If you take the standard deduction, can you still take the charity deduction?
“The charitable contribution deduction for non-itemizers expired and was not extended in 2022,” Bronnenkant said. “For people ages 70.5 or older, they can donate up to $100,000 per year from their IRA as a QCD (qualified charitable distribution) tax-free. This is true whether the taxpayer takes the standard deduction or itemizes.”
Can my wife file separately even if we live at the same address?
“Married filing separately is permissible while living at the same address,” Bronnenkant said. “While there are some rare exceptions, filing separately frequently results in a higher combined tax liability.”
I am on Social Security as my sole income, and I receive $1,100 per month. My out-of-pocket and other medical bills were about $30,000 in 2022. Do I need to file a tax return? And if so, should I take the standard deduction?
“The IRS states, ‘Generally, if Social Security benefits were your only income, your benefits are not taxable and you probably do not need to file a federal income tax return,'” Bronnenkant said. “However, if you elected to have any withholding taken out of your benefit, you would be required to file a tax return to claim a refund.”
Am I required to pay estimated quarterly taxes if my only source of income is my pension?
“Maybe,” Bronnenkant said.
“The IRS states that you have to pay the lesser of 90% of your current year tax or 100% of the prior year tax — 110% if last the AGI is greater than $150,000 — through withholding and/or estimated tax payments. If the pension withholding is not enough to meet these safe harbor requirements, estimated tax payments may be needed to avoid an underpayment penalty.”
If I received a Christmas gift of over $15,000, do I need to pay taxes on it?
“Gifts received — regardless of the amount — are exempt from income tax,” Bronnenkant said. “However, if the gift was used to purchase a bond that generates taxable interest, the interest received is taxable income.”
He added, “Note: The donor will have to file a Form 709 Gift Tax Return if the gift exceeds the annual exclusion — $16,000 for 2022 and $17,000 for 2023. Notably, gift taxes do not apply on the first $12.06 million of gifts in excess of the annual exclusions.”
I am a retired Air Force veteran. Do I have to pay taxes on my military retirement pay and VA wound pay?
“Military pensions are normally considered taxable income,” Bronnenkant said. “However, the portion of the pension that is for a service-connected disability would qualify for tax-free treatment. Thank you for your service!”
I am over 80 years old. What income must I pay taxes on?
“You may be receiving Social Security income. Typically, Social Security income alone is not taxable, but if you have other streams of income, like from retirement — reported on Form 1099-R — anywhere from 50% to 85% of a portion of your Social Security may be taxable,” said Lisa Greene-Lewis, CPA, tax expert with TurboTax.
“Remember, you may not have to file if your income is not over the standard deduction — $12,950 [for] single [filers] plus [an] additional $1,750 for being 65 and over.”
How do qualified dividends and capital gains figure into your adjusted gross income for tax purposes?
“Both qualified dividends and capital gains are figured into your adjusted gross income, but qualified dividends and long-term capital gains from investments sold after one year may be taxed at lower capital gains rates,” Greene-Lewis said.
“Also, don’t forget you can lower your capital gains — and in turn, ordinary income — by offsetting capital losses against capital gains.”
Can I claim my boyfriend’s kids on my taxes?
“You may be able to, but there are some stipulations,” Greene-Lewis said.
- They would be considered a non-relative, so they would have to live with you the entire year.
- You would need to provide over half of their support.
- Your boyfriend or anyone else could not claim them.
- They could not make over $4,400 taxable income.
- They have to be a U.S. citizen, U.S. National, or a resident of Canada or Mexico.
I had medical services performed in 2022, but they were not billed until 2023. Which tax year are they reported in — 2022 or 2023?
“Since individuals are on a cash basis, you can go by when you paid the bill,” Greene-Lewis said. “Make sure you have proof of your payment, like your bank statements or credit card bill.”
Do I have to report the money I get back from a credit card to the IRS?
“If the money you get back is a rebate based on your spending money on the credit card, it would not be taxable,” Greene-Lewis said.
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Gabrielle Olya contributed to the reporting for this article.