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May 2020 Tax Season Filing Tips

2020: When May became the new tax season's February.

Tax tip pencilNormally, this tax tip page would be full of post-filing advice. But, as we all know all too well by now, the coronavirus pandemic has made 2020 an incredibly abnormal tax season.

April 15 came and went without a frenzy of individual tax return filings. Those 1040s and lots of other tax tasks that the Internal Revenue Service previously has demanded be done by mid-April are now delayed until July 15. 

That effectively means that with ten weeks until Tax Day 2020, May is the new February. And that means that many of us are really just now getting into gear when it comes to filing our taxes.

Tax time vs. more freedom: This unusual situation where May is part of the active tax season also coincides with some COVID-19 changes.

Some states that had enforced stay-home orders to help slow the spread of the pandemic now are letting up on the lock-down.  That means, we hope, things will start returning to normal, or at least a new normal outside our houses.

That's good, as long as we follow Dr. Anthony Fauci's recommendations are are still cautious and diligent about social distancing!

But it also that means more chances for us to get distracted. If we're not careful, July 15, like the April 15 it's temporarily replaced, will suddenly be bearing down on us.

Taxes 2019 and 2020: So this May, we still need to make some tax moves so that we'll be ready when the filing due date arrives. Or before. As with the regular deadline, the IRS will gladly take your Form 1040 earlier.

We also need to be thinking about what the changes in our lives and jobs mean for our 2020 taxes. This month some of the tips will focus on those moves.

Either way, taxes are still here so here are the ol' blog's first ever May of filing season, not post-filing season, tips.

As with its predecessors, these May pieces of  tax advice are highlighted in the upper right corner of the ol' blog. And as is routine, after each tip's time in spotlight, it will join all the May tips here on this page.

Let's get to them!

  1. 5 COVID relief payment myths — There's no need for a mayday alert, on May Day or any other day, as long as you don't fall for these 5 coronavirus stimulus myths. (May 1, 2020)
  2. May the Tax Fourth Be With You: COVID-19 sequel — In a galaxy very close to home, taxes are always critical. This year, coronavirus considerations offer some different takes on the annual Star Wars' inspired May the Tax Fourth Be With You sequel. (May 4, 2020)
  3. Charitable tax guidelines, COVID-19 changes — The tax rules for donating, along with myriad (and out-of-the-ordinary) ways to give provide philanthropic and tax-saving options for donors beyond May 5's special #GivingTuesdayNow. (May 5, 2020)
  4. May 13 is COVID-19 relief direct deposit deadline — If you want your COVID-19 economic relief payment directly deposited in your bank account act now. Or at least by May 13. That's the deadline to use the Internal Revenue Service's online Get My Payment tool to provide your financial institution info so your coronavirus cash goes there instead of coming to you as a mailed Treasury check. (May 9, 2020)
  5. 6 reasons your COVID-19 payment was short — You got your COVID-19 economic impact payment (EIP). Yay! But it was less than you expected. Boo! Here are some reasons why that might have happened and how you might get the rest … but not until next year. (May 11, 2020)
  6. FSA, other benefit changes under COVID-19 — COVID-19's disruptions continue, this time affecting people's tax-favored workplace-provided benefits. To help ease those problems, the IRS has issued a couple of notices that allow changes to things like medical spending accounts and dependent care assistance programs. The goal is to give employees more flexibility to adjust benefits in this uncertain time. (May 12, 2020)
  7. Homeowner's insurance is tax deductible in some situations — Owning a home is costly. But one of those expenses, your property's hazard insurance, might be at least partially tax deductible. That's the case if you're self-employed and work from home. (May 14, 2020)
  8. Hurricane prep time is here — The 2020 Atlantic hurricane season is off to an early start, just like happened last year. Fortunately, Tropical Storm Arthur didn't cause many problems to U.S. coastal residents. But the early storm is a good reminder that we need to prepare now. Here are some disaster kit tips, as well as financial and tax issues to consider, along with this year's storm names. (May 17, 2020)
  9. File beyond 7/15 with IRS' OK — Tax Day 2020 is three months later than usual thanks to COVID-19 complications. Still, some folks will find they need more time as July 15 nears. No worries. You can still use Internal Revenue Service Form 4868 to get an extension until Oct. 15. (May 19, 2020)
  10. Tax-free COVID payments in most states — Across most of the United States, the federal COVID-19 economic relief payments aren't taxable at any level. However, a handful of states' tax laws mean their residents could see these stimulus amounts taxed at the state level. Some of those states now are taking action to ensure that doesn't happen. (May 20, 2020)
  11. Inflation increase for high deductible medical savings plans — Looking for medical insurance with lower premiums? A high deductible health plan (HDHP) could be just the thing, especially when you add a health savings account (HSA). Here are the IRS' annual 2021 adjustments to this tax-favored medical option. And don't forget you also still have time to up your 2019 contributions. (May 21, 2020)
  12. Some COVID-19 payments are on debit cards — Don't have a bank account? No worries, says the Treasury Department. It's sending out a star-spangled debit card with your qualifying COVID-19 economic relief payment amount loaded on it. So look for the unmarked envelope from MetaBank in your snail mail box and don't throw away the card! (May 22, 2020)
  13. Expat tax break could increase COVID-19 payments — Living in Paris and getting a larger COVID-19 relief payment than you would have if you worked in the United States? That's the deal for some expats, and not just those in The City of Light, thanks to a special foreign income tax exemption. (May 23, 2020)
  14. HSAs mean tax savings & more filing tasks — High deductible health plans (HDHP) and associated health savings accounts (HSA) can help you save medical tax dollars. The health care choice, however, requires another tax task. You'll have to file Form 8889. (May 26, 2020)
  15. Form 1040-X going digital this summer — Good news for taxpayers who want to amend a tax filing mistake: the IRS will accept some 1040-X e-filings later this summer. It's only for 2019 tax corrections, but it's a start. (May 28, 2020)

*****

Just getting started on your taxes? No problem. You can find the previous months' collected tax wisdom by clicking the links below.

And yes, you can click on May, June and June, too, but you'll just find a guy telling you to whoa up. We're not there yet. Rest assured, those tips will be added as those months arrive.

January 2020 Filing Season Tax Tips

February 2020 Filing Season Tax Tips

March 2020 Filing Season Tax Tips

April 2020 Filing Season Tax Tips

June 2020 Filing Season Tax Tips

July 2020 Filing Season Tax Tips

Coronavirus Caveat & More Information
In 2020, we're all dealing with extraordinary circumstances,
both in our daily lives and when it comes to our taxes.
The COVID-19 pandemic and efforts to reduce its transmission
and protect ourselves and our families means that,
for the most part, we're focusing on just getting through these trying days.

But life as we knew it before the coronavirus will return,
along with our mundane tax matters.
Here's hoping that happens soon!
In the meantime, you can find more on the virus and its effects on our taxes
by clicking Coronavirus (COVID-19) and Taxes.

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Today's Tax Tip

  • Added summer income means more tax considerations — If you’re taking on added jobs this summer instead of taking a vacation, be aware of the tax implications. Students at their first paying job are encountering the Internal Revenue Service for the first time. And workers well past their school days but who are earning extra via summer gigs could face new self-employment tax challenges. (June 15, 2025)


  • Tax Tip; click pencil for all tax tip links

  • The 2025 Tax Tips offer ways to file your annual return, along with post-filing advice, important tax news and, of course, ways to cut your current tax year bill. You'll find the monthly assemblages on their own respective pages: January, February, March, April, May, June, July, August, September, October, November and December. Remember, tax tasks and tips don't stop after you file your annual return!

All About Kay

  • OK, some about Kay
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    Kay Bell — Native Texan
    (the blog title totally makes sense now, right?). Professional journalist. Tax geek.
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  • Tax Year 2025 Continues!

    We made it. Tax Day 2025 is finally over. For most of us. When the filing season started on Jan. 27, the IRS said it expected more than 140 million individual tax returns for tax year 2024 to be filed by April 15. When the month started, the agency was around 39 million short of that number. While many taxpayers no doubt got their 1040s in by Tax Day, million every year get an extension to file. That's fine.

    In fact, the Internal Revenue Service appreciates some of us spreading out our tax submissions. It gives the agency time to process the surge of returns that arrive en masse on April 15.

    But enough about Uncle Sam's tax collection issues. The focus now is on all y'all who filed for extensions, giving you another six months to complete your return. Let's get started on meeting that new Oct. 15 deadline. It will be here before you know it.

    The monthly tips and reminders a little further down this column can help you finish up your extended Form 1040. There also will be tax tidbits each month that make sure you meet other tax deadlines. And, of course, you'll find advice on ways to cut your 2025 tax bill.

    The monthly tips and reminders a little further down this column can help you finish up your extended Form 1040. There also will be tax tidbits each month that make sure you meet other tax deadlines. And, of course, you'll find advice on ways to cut your 2025 tax bill.
    Note: I'm in the Central Time Zone, so adjust accordingly for where you live.


Time for Tax Tasks


  • monthly tax moves


  • ☀️ Hello 🌞 June! ☀️
    Your radiant face, bringing us the start of summer, is long overdue. We need your consistent warmth and a sunny attitude to fully recover from tax season, even one that didn’t throw us too many curveballs.

    via GIPHY


    And let’s be honest. We’re not really in the mood for summer tax tasks. But there are some that do need attention, especially if you got an extension to file back in April. Taking care of these tax matters now can make the coming 2026 filing season go smoothly. Even better, some tax moves can mean you’ll owe Uncle Sam less. So grab your sun visor, and let’s get to them!


  • June 1: Summer conjures dreams of lazy beach days. But for full-time coastal residents, June also brings the start of the annual Atlantic (and Gulf of Mexico) hurricane season, which runs through Nov.  30. Federal forecasters once again are forecasting a more active than usual hurricane season. And while the tropical storm season heats up in August and September, now is the time to get ready.

    Hurricane satellite image

    Uncle Sam's official forecasters at the National Oceanic and Atmospheric Administration (NOAA) Climate Prediction Center say we could get 13 to 19 total named storms, which are those with winds of 39 mph or higher. Of those, six to 10 are forecast to become hurricanes, meaning winds of 74 mph or higher. Three to five of the storms this season could become major hurricanes; that’s category 3, 4 or 5, with winds of 111 mph or higher.



    Regardless of the count, it only takes one to wreak havoc. The countdown clock above can help you keep track of how many more days you have to worry about tracking any size or type of tropical storms. You also might want to check out the ol' blog's Storm Warnings collection of special pages with posts offer tax advice on preparing for, recovering from and helping those who sustain damages from the many ways that that weather goes wild.

    June 6: With school out, working parents need to make child care arrangements. Consider day camps. I know, many filled up earlier this year, but check out the options in your area. Not only do day camps offer some supervision of your kiddos while you're at the office, the activities' costs also count toward claiming the child and dependent care credit.

    June 10: If your job is as a server at a restaurant or at any other establishment where gratuities from customers are part of your compensation, I hope you get all the tips you deserve for doing your job well. Remember, though, that those tips are taxable income.

    restaurant check tip iStock
    Whether you're dining at your favorite eatery or getting food, groceries and/or prepared meals, delivered to your home, if a tip isn't included on your restaurant or delivery bill, click the image above to calculate how much to tip the person who brought it to you.

    If you got at least $20 in gratuities in May for your extraordinary services as a food server or hair stylist or parking valet or whatever job where tipping is common, you must report that amount by today. Use Form 4070 to let your employer know the total tips you took in last month.

    June 14: Happy Flag Day! It's not a day-off-work federal holiday, but Flag Day has been an official day to celebrate the Star-Spangled Banner since 1949. If you need to buy a U.S. flag to fly today, you also might get a tax break. Several states exempt the national symbol from sales tax. Check with your state's tax department to see if you can save on your patriotic display.

    June 15: Happy Father's Day!

    Happy Father's Day


    Dad might not say so, but he appreciates being recognized, so take time today to let him know you care. And if your father is getting on up in years, take the time when you visit to make sure he doesn't need some added help from you. If you provide papa a little, or even a lot of assistance, there's a chance you could get some help from a couple of tax credits.

    June 16: It's Tax Day again, this time for taxpayers living and working abroad. That includes military personnel posted outside the United States or Puerto Rico. This automatic filing delay until mid-June officially is on 6/15, but is a day later this year because the 15th was on Sunday.

    Today, June 16, also is the one-day-later deadline for the second estimated tax payment for the 2025 tax year.

    June 19: It's Juneteenth. This date marks when Texans finally received word that all slaves were free. And although it is our newest federal holiday, and is celebrated on June 19, not on a nearby Monday, it is the oldest nationally celebrated commemoration of the ending of slavery in the United States.

    Juneteenth


    June 20: At 10:42 p.m. Eastern Time it’s official. Summer is here, arriving on this longest day of the year.

    Summer sun

    It’s also a dangerous season for many who don’t have air conditioning. Many charitable groups help people cope with the heat. If you itemize, your gift to such IRS-qualified nonprofits this summer — or any day in any season in 2025 — could be tax deductible on the tax return you file next year.

    June 30: If you got an extension to file back in April, you don’t have to wait until the final Oct. 15 deadline to do so. You can get this tax task out of the way so you don’t have to think about it for the rest of the summer. You also might be able to file electroncally at no cost if your adjusted gross income (AGI), regardless of your filing status, is $84,000 or less by using the official IRS.gov Free File website.

    IRS Free File; click image for details

    Eight software companies are part of this year’s IRS-Free File Alliance partnership option at IRS.gov. They will be available through the Oct. 15 extension deadline, but again, you don’t have to wait. And if your income is too high, you still can file for free by using Free File's Fillable Forms option.

    Small Business Tax Calendar: If you run your own company, you know there are myriad important filing, deposit and record keeping dates throughout the year that your company needs to meet. You also can track key business and individual tax deadlines in IRS Pub. 509.

State Tax Help

  • Don't forget your state taxes!
    Forty-two states and D.C. collect personal income taxes. But even if you live in of the eight states without any income levy, you still face other state (and local) taxes.

    State Tax Departments provides links to your state's Web page. The companion page, Tax Tidbits, is the compilation of blurbs about each state's tax laws. And for more state tax news, check out all our state tax bloggings.

Tax Forms


  • Tax Forms
    Thanks to our increased use of tax preparers and computer software, many of us don't see our tax forms until we sign and file them. But knowing what's on these documents, either in paper or digital form, and why the IRS wants it is key to understanding our tax system. And knowledge definitely is power, especially when it comes to tax savings. Find this valuable information in the ol' blog's special Tax Forms 2025 page.

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    I am a professional journalist who has been covering tax issues since 1999. I am not a professional tax preparer.

    The content on Don't Mess With Taxes is my personal interpretation and opinion based on my study and understanding of tax laws, policies, and regulations. It is provided for your private, noncommercial, educational, and informational purposes only. While I work to ensure each post's accuracy, the items are not recommendations of any specific tax action(s) you should or should not take. Similarly, mentions of commercial tax products or services are not endorsements.

    In other words, my ramblings on the ol' tax blog are free advice, and you know what they say about getting what you pay for. That's why when it is time for you to file your own taxes, I urge you to get additional, professional, paid-for guidance from an accountant, Enrolled Agent, or other reputable, qualified tax preparer who is familiar with your individual tax circumstances.

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COVID-19 & Taxes

  • COVID-19
    Coronavirus has wreaked havoc
    on the 2020 and 2021 tax seasons.
    These five Coronavirus (COVID-19) and Taxes pages have details:
    March-July 2020
    August-December 2020
    January-December 2021
    January-December 2022
    …and so it continues into 2023
    …and, alas, into 2024
    It is 2025 and, yes, it's still an issue
    You can find medical coronavirus resource links in the next section.

COVID-19 Resources

  • COVID-19
    Need help finding a coronavirus vaccine in the United States?
    Call 1-800-232-0233
    or TTY 1-888-720-7489.
    More information and resources at:
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    USA.Gov COVID Info

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Tell it to the Hill

  • DMWT Politics Posts
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