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13 tax tips for the 2019 filing season’s last weekend

April 13, 2019
Wading bird_I Am birdsaspoetry via Flickr CC

This wading bird doesn't mind being knee-deep, but it's not a good position if you're trying to dig through your taxes on this last weekend of the filing season. (Photo by I Am birdsaspoetry.com via Flickr CC)

We're knee- or in some cases neck-deep into the final days of Tax Season 2019. How's it going for you?

If you're among the more than 103 million U.S. taxpayers who have already filed their returns, you're probably feeling pretty good about things.

So is Charles Rettig, who's overseeing his first federal filing season as commissioner of the Internal Revenue Service.

"The filing season continues to go well in terms of tax return processing and the operation of our information technology systems," Rettig told Senate Finance Committee members on April 10.

"During my first few months here, I have been extremely impressed by how hard IRS employees all across the agency have worked to make sure taxpayers have a smooth filing experience this year," said Rettig, as reported by Michael Cohn for Accounting Today. "This is especially impressive given the need to implement so many major changes made by the Tax Cuts and Jobs Act. With hundreds of provisions providing relief to American families and making America’s businesses more competitive, the TCJA required extensive work by the IRS to ensure taxpayers would be able to meet their filing obligations this filing season."

Cohn's article with more on Rettig's take on this filing season and Senators' reactions gets this weekend's Saturday Shout Out. If you're done with your taxes, I recommend you read it.

The commish also posted on IRS.gov a message directly to all us taxpayers, basically thanking us "for taking the time to file and pay [our] taxes" and helping "make our tax system a model for the entire world." Yay taxes and us! And a secondary shout out to Rettig.

If, however, you're still working on your return and bounced over here looking for some last-minute filing tips, here are a dozen posts that should help keep this last tax weekend from turning into your return's Lost Weekend.

OK, maybe that 1945 Ray Milland classic film isn't the best metaphor. Then again, after dealing with taxes as the deadline bears down, you might want a drink or two. But I digress. Here are the tips:

  1. Filing a tax return: Who must, who should 
  2. New 1040 form and schedules 
  3. 2018 tax return checklist and Schedule A review 
  4. 5 Free File tips 
  5. 10 common tax mistakes 
  6. 22 tax deductions that don't require itemizing
  7. Gig economy tax tips 
  8. Picking the proper filing status 
  9. Obamacare 2018 tax year filing requirements
  10. 20% small business pass-through tax deduction
  11. Ways to pay your tax bill 
  12. Take care of your state taxes, too
  13. How to get a tax-filing extension

If you want even more tax tips, you can check out the monthly collections: January, February, March and — tah-dah! — April.

Extend to avoid mistakes: At this late hour in the filing season, I want to emphasize #13.

Yes, you still have the rest of the weekend and until midnight April 15 (or April 17 if you live in Maine or Massachusetts). That's plenty of time to finish the job, especially if you're already into filling out your forms.

However, if you're just now looking for a tax software to use — I know you're not searching for a tax preparer, as most reputable ones are finalizing the forms for their current clients and aren't taking on any new customers — you might want to skip to the part of the computer program that lets you file for an extension.

Unless your return is very simple, it's going to take you more time that you realize to finish. And you're likely to get frustrated and possibly take shortcuts just to be done with it all.

That could mean you end up making a costly mistake or worse hear back from the IRS about your filing.

Believe me, the IRS really doesn't want to have to question you either. Its workers have plenty of other things to do than track down relatively small filing discrepancies.

So do yourself and the IRS a favor. Take all the time you need to submit a properly completed Form 1040, even if you do so a few weeks from now.

And for all y'all putting on the final finishes on and double checking your 2018 tax returns, congrats! I'll let you get back to work so you can be done with taxes and enjoy the rest of your weekend.

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The More Tax Posts tab at the top of this page will take you to, well, more tax posts. You also can search below for a tax topic. 

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TO WRAP UP 2026

It’s over! With October’s extended filing deadline behind us, it is now time to focus on year-end moves to reduce your 2026 tax bill. 

You’ll find ways to do just that on the Tax Tips page (see the More Tax Posts drop-down menu at the top of the blog), as well as the separate tax tip pages for each month, notably October through December. If you’re on the Tax Tips page, you’ll find a monthly list at the end of this column. If you’re on another blog page, you can head straight to the October tips; at the bottom of that tips page you’ll find links to all the other 11 months’ collections of tax advice.

Not to spoil what you’ll find in that tax advice, but it does cover such things as tax deductions for charitable donations, investment moves that could reduce tax due, and ways to max out your tax-favored retirement savings. 

Finally, as the year winds down, things get hectic. There are lots of other things to occupy our time, like the much more fun upcoming holidays. But don’t lose sight of taxes, since timing is key. To be of use, most tax moves must be made by the end of the tax year. That’s Thursday, Dec. 31, which also is the last business day of the year. 

So that you don’t miss that final tax year deadline, also keep an eye on the countdown clock below. It will keep you on top of just how much time is left to make important, tax-saving moves. (Note: I’m in the Central Time Zone, so adjust accordingly for where you live.)

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