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Weekly Tax Tips 2019

Tax Day is gone, but the tax fun keeps rolling along!

Tax tip pencil

Hallelujah! Tax Days 2019 — and yes, Days is correct, since there were two April deadlines this year — are done!

Now it's time to downshift our tax focus a bit.

Sure, some of us got an extension to file our 1040s by Oct. 15.

And others will likely discover they need to correct an entry or two and will amend their 2018 taxes sometime this year.

But for the most part, it's time to focus on what we can and should do for the rest of 2019 to limit or reduce this year's tax bill.

It should be a bit easier since we just made it through the first filing season under the new Tax Cuts and Jobs Act (TCJA) changes.

And since we don't have major deadlines to meet — just make our estimated payments on time over the next few months and, for many of us, finally finish our extended 2018 returns by mid-October — tax matters aren't so hectic.

So the ol' blog has shifted to our annual Weekly Tax Tips.

Once a week through 2019: As in previous years, a new piece of tax advice will be featured each week, usually each Friday. I know, it's a perfect lead-in to weekend tax reading!

And it's still in the upper right corner of the ol' blog.

Many of the items will be for the majority of taxpayers who are done with their tax year 2018 returns and now are looking for ways to trim this year's tax bill.

A few, though, will be aimed at helping those of us who've yet to file get that job done, especially as October nears.

The once-a-week tax tips will continue, as they've done in past years, until 2019 is a wrap. That will be on Dec. 27, the last Friday of this year.

Also, don't be surprised if a stray weekly tip or two also shows up in the opening week/weeks of January 2020 before I transition to the New Year and the return of the 2020 Filing Season Tips.

But wait. I'm getting a bit ahead of myself. There's lots of 2019 left.

So let's get back to this year and the latest round of Weekly Tax Tips. Here goes!

  1. Missed Tax Day? Do this now — Some folks didn't file their federal taxes on April 15 (or 17). If you're among those who missed the deadline and also neglected to get an extension, you need to make these four tax moves ASAP. (April 17, 2019)
  2. Tax record keeping tips — Now that you've filed your taxes, it's time to deal with all the materials, either literally or digitally, that you used to fill out your Form 1040. You should keep most of the documents for at least a few years. (April 25, 2019)
  3. Employee or contractor distinctions — How a job is done makes a big tax difference to both employers and workers. With the trend today toward a gig economy, the variables determining whether a worker is an employee or independent contractor is even more critical. Here's what the IRS says about making the payroll call. (May 3, 2019)
  4. How kids can help cut your tax bill — The Duke and Duchess of Sussex, aka Harry and Meghan, don't qualify for (or need) them to care for their new son Archie, but these five popular U.S. tax breaks can help us non-royals offset the ever-escalating cost of child rearing. (May 10, 2019)
  5. Form 1040X gives you a filing do-over — Made a mistake on your 1040? Found a tax break you overlooked? Then Uncle Sam's X file, aka Form 1040X that lets you amend prior filings, can help you get the truth about your taxes to the Internal Revenue Service. (May 17, 2019)
  6. Time to assess, adjust withholding — With all the Tax Cuts and Jobs Act changes, the IRS eased up on underwithholding penalties for the 2018 tax year. That's not happening with our 2019 returns. So now is a good time to examine and, if necessary, adjust how much tax you're having withheld from your paycheck. (May 24, 2019)
  7. Take a pre-disaster inventory — It's hurricane season again. One of the first moves you should make is taking a pre-disaster inventory of your household goods. It will help you file insurance claims and, if the catastrophe is declared a major disaster, you could also get some federal tax relief. (May 31, 2019)
  8. Wedding tax tips — Regardless of whether you tie the know in June or some other month, you'll have some tax tasks to take care of once you get back from your honeymoon. Here are 6 tax moves that newlyweds should make. (June 7, 2019)
  9. Appealing an IRS decision — You and the Internal Revenue Service disagree about what you owe. The tax collector's finding isn't necessarily the final word. You can appeal. Here's how. (June 14, 2019)
  10. Day camp tax break — School's out for the summer. If you're sending your children to day camp, hold onto the receipts. Not only do these seasonal diversions give working parents some peace of mind about who's taking care of their kiddos now that classes are done, camp costs count toward claiming the child and dependent care tax credit. (June 21, 2019)
  11. DSIRE-able government help to PACE your summer energy usage — Summer is just beginning, but it's not too soon to think about tuning up your air conditioning system or replacing it with a more energy efficient unit. In some states, PACE loan programs can help. Others types of assistance are tracked by DSIRE, the Database of State Incentives for Renewables and Efficiency. And Congress is looking into renewing a tax credit that would provide a bit of a federal tax break for energy efficient home improvements. (June 28, 2019)
  12. Maximizing business meal tax deductions — The Tax Cuts and Jobs Act kept, for the most part, the tax deduction for business meals in the tax code. Here's how to make sure you get the most tax benefit from those work-related dining experiences. (July 5, 2019)
  13. 5 disaster preparedness moves for businesses — Hurricane Season 2019 is underway. We've had two storms so far, with the annual storm number peaking in September. That will be here before your know it. So in addition to making individual storm (and tax) preparation moves, if you're the boss check out these ways to get your business ready for any disaster. (July 12, 2019)
  14. 6 sales tax holiday shopping tips — Sixteen states are holding sales tax holidays this year. If you plan on shopping during one of them, these six tips can help you maximize your tax and overall savings and minimize the mall hassle. (July 19, 2019)
  15. Know your tax notices — The Internal Revenue Service is sending letters to virtual currency owners, but there are lots of other notices issued by Uncle Sam's tax collector. Here's a look at the IRS' most common error and/or payment notices, along with some tips on how to handle them. (July 26, 2019)
  16. Capital gains taxes under the new tax law — The Internal Revenue Service is alerting virtual currency owners of the taxes they owe on that new-fangled asset. But owners of traditional assets who sell them for a profit also face capital gains taxes. Check out what the investment earnings' tax rates are under the Tax Cuts and Jobs Act and with the latest income inflation adjustments. (Aug. 2, 2019)
  17. 3 popular retirement plans for the self-employed — One of your tasks when you're the boss of yourself is to take care of your business retirement plan. Self-employed workers have a variety of options that can help you save for your post-work years plus cut your current tax bill. (Aug. 9, 2019)
  18. Tax differences of home repair vs. home improvement — Keeping up a house takes a lot of work. In some cases, generally where you improve the property, the effort could help lower or eliminate a possible tax bill. In others, where you simply take care of necessary repairs, you'll make the place better, but without any tax benefit. (Aug. 16, 2019)
  19. Getting tax credit for relatives (and others) — Taking care of a lot of folks? You might be able to get a tax break under the Tax Credit for Other Dependents, which per the Internal Revenue Service definition could include those not technically related to you, as long as they (and you) meet the requirements. (Aug. 23, 2019)
  20. Reconstructing tax and other records — You and your family made it through the storm, but your property took a hit. You need to file for available tax relief, but can't find all the documents you need. The Internal Revenue Service can help with the necessary tax material. Check out these tips on how to reconstruct tax and other records. (Aug. 30, 2019)
  21. Tax help for disaster losses — It's the busiest time of the hurricane season. If you're in a storm's path, you might be able to get some tax help to make your recovery smoother. Losses from a major disaster can be claimed on your taxes next filing season or by amending your prior year's return. (Sept. 6, 2019)
  22. Avoiding too-high taxes on damaged property — What's worse than losing your home to a disaster? Having to pay taxes on the destroyed property. That's why you need to let your local tax officials know as soon as possible after your taxable property was seriously damaged or destroyed, regardless of whether by Mother Nature or some other calamity. (Sept. 13, 2019)
  23. Home basis key in making disaster loss claims — When making major disaster loss claims on your tax return, your damaged or destroyed home's value is key. To arrive at that amount, you must take into account the property's basis. (Sept. 20, 2019)
  24. Don't miss these 4 Oct. 15 tax deadlines — Weather is unpredictable in early fall, but there's one October certainty: the mid-month tax deadline. Here are four tax tasks to take care of by Oct. 15. (Oct. 4, 2019)
  25. Oct. 15 tax extension filing tips — If you got an extension to file your tax return, then you're facing that looming Oct. 15 final filing deadline. These 9 tips can help you get it done on time. (Oct. 11, 2019)
  26. Where's your refund? — Whether you finally filed your taxes on the Oct. 15 extension deadline or got them in earlier, you're now eagerly anticipating the refund you're due. The Internal Revenue Service's online Where's My Refund? tool can help you track your tax cash. (Oct. 18, 2019)
  27. Picking the best workplace benefits — It's the heart of open season at many companies, when employees make their annual workplace benefits selections. Many of the options, such as 401(k)s and flexible spending accounts, provide workers nice and immediate tax savings. These five considerations can help you choose the perks that fit your needs, tax and otherwise. (Oct. 25, 2019)
  28. Tax-smart ways to be done with Halloween candy — Did you over estimate the number of trick-or-treaters? Me, too. But rather than face down that caloric temptation, donate it! It will be welcome by many recipients, your waistline and possibly as a charitable deduction at tax-filing time. (Nov. 1, 2019)
  29. Tax breaks for military veterans — Much of our tax money goes to the military. Veterans Day, the 11th day of the 11th month, is set aside to officially remember and honor those armed forces members who sacrificed, sometimes ultimately, to protect us. But beyond this holiday, there are ways the tax code can help our service men and women, both those still on duty or having competed their obligations. (Nov. 8, 2019)
  30. Inflation's effects on 2020 taxes — Inflation shows up in more than just what you spend at the grocery store. Find out what the higher cost of living will mean to your taxes in the annual look at coming changes to amounts of some popular tax provisions. The revisions affect 2020's income tax brackets, how much you save for retirement in tax-favored accounts, tax-deductible medical expenses and much more. (Nov. 15, 2019)
  31. Seasonal job tax and scam tips — It's seasonal job season. Even the Internal Revenue Service is looking for help this time of year. Just be aware of the tax implications of added work. And definitely don't fall for any employment scams in your job search. (Nov. 22, 2019)
  32. States also offer health insurance marketplaces — The federal health care marketplace is offering plans though Dec. 15. More than a dozen states also provide marketplace options to their medical coverage shoppers. And although the federal enrollment mandate and penalty is gone, some states still require their residents to get coverage or pay a price. (Nov. 29, 2019)
  33. End-of-year tax tips — 2019 is almost over! When you have some time between holiday parties and shopping, check out these business tax moves. Individual filers also will find in this post some links to year-end tax moves they should make, too. Happy holidays and smaller tax bills for all! (Dec. 7, 2019)
  34. Checking out charities — The option to deduct charitable donations has taken a hit thanks to recent tax law changes. But many folks still give, with or without the write-off. Either way, you need to make sure your charity is nice, not naughty. Here are ways to do that. (Dec. 13, 2019)
  35. 5 more tax moves to make by Dec. 31 — Yes, you have a holiday hangover. And yes, you still have to go back into your office as 2019 winds down. But with these last few days of the tax year upon us, you also need to check out these final five tax moves to make by New Year's Eve. Then you'll really have something to toast! (Dec. 27, 2019)

And for all y'all still working on your extension or discovering you need to amend your original 2018 taxes, you can always get filing insights by checking out the 2019 Filing Season Tax Tips that are collected on their own monthly pages: January, February, March and through Tax Day in April.

 

 

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Today's Tax Tip

  • Tax-saving HSA contribution limits go up in 2026 — The amounts that health savings account (HSA) owners can put into this tax-advantaged medical plan is going up next year. The increase is part of the IRS’ adjustment this week of the 2026 limits for HSAs, associated high deductible health plans (HDHPs), and the lesser-used health reimbursement arrangement (HRA). (May 2, 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
    Open sign
    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


  • 💐 May 💐 is 💐 here! 💐

    You've got to love a month that starts with a celebration, at least globally. But even though May Day isn’t an official or very big deal here in the United States, there still are lots of other May celebrations. Cinco de Mayo. Mother’s Day. Memorial Day.

    May Pole Dance via GIPHY


    In between, we can celebrate the arrival of the month that, for most taxpayers, means the main 2025 tax task of filing our returns is behind us. Now it’s on to shower-fed flowers, balmy days, and additional tax moves to take care of so that the rest of the year goes smoothly. Let the May tax merriment begin!


  • May 1: It’s not such a merry day for some taxpayers. Not only did the residents of eight states have to earlier deal with a major natural disaster, their Tax Day that was delayed because of those damages is today, May Day, no doubt prompting a mayday call from some affected filers.

    May 2: The rest of us made it through last month, the one that is home to the annual U.S. filing deadline. Did Tax Day mean you got or are expecting a big refund from that filing? Or did you end up owing Uncle Sam a lot? Either way, with your most recent taxes fresh in your mind, it's a good time for a paycheck checkup to determine whether you should adjust your payroll income tax withholding.

    May 5: ¡Feliz Cinco de Mayo! Fiestas are always en vogue in Tejas, but the epitome of them is this Mexican holiday.

    Feliz Cinco de Mayo

    No, it is NOT Mexican Independence Day, and May 5 tends to spur more festivities here north of the border, especially when it comes to imbibing margaritas, the Lone Star State's unofficial cocktail. With every Cinco toast, remember that the cost of state and federal alcohol taxes are included in the mixing.

    May 11: Happy Mother's Day!

    Happy Mother's Day

    Your mom meant it when you were young and she told you she didn’t need a gift today. But she definitely will appreciate a longer-than-usual hug on her special day. Love, flowers, and the best of health and happiness to every mother, from the new ones just discovering the joys, tax and otherwise, of new parenthood to those gracefully maneuvering their Golden Years and getting some year-round tax-advantaged help from their families.

    May 12: 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.

    And if you got at least $20 in gratuities in April 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, a bit late since the normal 10th of the month deadline fell in May on Saturday. Use Form 4070 to let your employer know the total tips you took in last month.

    May 19: Millions of taxpayers got an extension to file, or automatically got a later Tax Day due to a major disaster declaration. These individuals can still file electronically, which the IRS recommends. E-filing will speed up processing of returns whenever they are filed, as well as help Uncle Sam get refunds out more quickly. And yes, some late filers are due refunds.

    The IRS-Free File Alliance partnership offers no-cost online tax preparation and electronic filing to taxpayers whose adjusted gross income (AGI) is $84,000 or less, regardless of filing status at the official IRS.gov Free File website.

    Even better for eligible late filers, Free File will be available through the Oct. 15 extension deadline, with the same eight software companies that participated last year back for the 2025 filing season.

    IRS Free File; click image for details

    If your income is too high, you still can file for free by using Free File's Fillable Forms option.

    May 23: Millions of Americans will be welcoming the unofficial start of summer this long Memorial Day weekend. It’s also when gasoline prices always seem to increase. Some of the pump price is attributable to fuel excise taxes. If pump prices climb too much, that may prompt you to look more closely into getting an electric vehicle (EV) before your next road trip, and before the current White House and Congress eliminate the potential $7,500 tax credit for some EVs.

    May 26: Yes, the end-of-May long weekend is a time for fun. But don’t forget the real reason for the Memorial Day holiday. Take time to honor the military personnel who made the ultimate sacrifice. And don't forget about their families. There are some tax considerations offered survivors of lost soldiers, sailors, and air crew.

    May 31: You filed your tax return six-plus weeks ago and you’re still waiting on your refund. What the what?! Quit fuming and check your refund’s status using the IRS' "Where's My Refund?" online tracking tool.

    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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    You also might enjoy these other tax tips from some of my tax-writing colleagues:

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I gotta tell ya ...

  • AKA Disclaimer:

    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
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    Call 1-800-232-0233
    or TTY 1-888-720-7489.
    More information and resources at:
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May 2025

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Tell it to the Hill

  • DMWT Politics Posts
  • While it's easy to rail at the IRS, for the most part we can thank — or blame — Congress and the White House for our tax laws. So if you have an issue with tax legislation or want a tax bill passed, you need to let your federal legislators and the White House occupant know of your concerns. You can find out who in Washington, D.C., to contact (and how), as well as get information on your local lawmakers for matters, tax or otherwise, closer to home, at USA Gov.
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