Doing Your Taxes at the Last Minute—or Filing for an Extension—Is Easier Than You Think

Time to go to war with your inner tax procrastinator.
April 16, 2018, 2:12pm

As a freelancer with multiple 1099s coming in around the country, filing taxes isn’t as easy as drag-and-dropping numbers from one document to the other. Instead, it involves combing through a mountain of receipts, making sure everyone who was supposed to send me a tax document did, and carefully carrying enough ones to splinter my abacus. It’s not a fun process.

And yet, I’m a tax procrastinator, and I’m not alone. Last year, more than 21.5 million Americans waited until the last week to file their taxes. Perhaps you’re one of them. It’s certainly not a bad thing—deadlines are deadlines for a reason—but there are a few things you should be aware of if you drag your feet filing returns.


The first is whether or not you’ll be forced to file them on your own. It would seem that most tax preparers are overly occupied this time of year, and perhaps don’t have time to handle new clients, and that’s sort of true. But luckily, it also doesn’t exactly matter! “Nobody is just going to be turned away,” says Jackie Pearlman from The Tax Institute at H&R Block. “The door is not going to be shut.”

So you probably can get help. But in most cases it's cheaper—or even free—to do it yourself. Whichever route you choose, here are some tips for filing your taxes at the last minute:

DIY your taxes on the fly

Are you, unlike myself, someone with, ahem, a "real job" and therefore just have a single W-2 from your employer to report Do you not have any special deductions like houses or kids? Then you can likely still get it all done yourself, in the next hour or so, using free or paid software you can access online from places like TurboTax, TaxAct and Credit Karma.

Lost your W2? Many employers upload those documents to sites like MyTaxForm, which can then be automatically uploaded into software like TurboTax. Just check your work email or ask HR. The whole thing takes a minute.

But don’t get sloppy! Kiplinger has listed a handful of things that late-filers often overlook while they’re rushing around like banshees.

For starters, be certain to double-check, or even triple-check, all the Social Security numbers and bank routing numbers you input, and make sure to sign and date the damn thing when it’s done. Try to keep your tax returns from previous years handy, for reference and security questions, especially if you are using a certain brand of efiling software for the first time. And make sure to add up all of your charitable contributions—which include expenses like mileage, parking, and tolls accrued doing volunteer work—so that you can maximize your refund.


Also, as Kiplinger points out, if you’re confident that you’re getting a refund this year, maybe just calm the hell down? “The IRS will gladly hold on to your money until you get around to filing your return,” they write, “if ever.” Best of all, there's no fine if you miss the tax deadline when Uncle Sam owes you money—and chances are, he does.

Wave a white flag—the right way

Whether you’re having your taxes prepared by a professional or doing them on your own, remember that you can always file for an extension. This is a fine, normal, and not at all shameful thing to do!

“Many people are fearful of doing this, but there’s nothing to fear at all,” says Ric Edelman, founder and executive chairman of Edelman Financial. “It’s all very routine. Millions file extensions. I do it as well, and have for decades.”

It’s an extremely simple action to take through the IRS’s own website, and you don’t even need to give them a reason. In fact, last year, nearly 13 million people filed extensions. It gave them—and could give you!—an extra six months to put their various forms in order and send them in. For the late filers this year, that means tax day isn’t until October 17th. Why drive yourself nuts when you can leisurely do them over a Halloween movie marathon!

It makes sense, then, that everyone I spoke to said there’s no reason to expect tax preparers to charge “surge pricing” for tax procrastinators, seeing as they won’t be rushing with the extended deadline. “Some accountants even charge less to do the work for you in the summer time because they're not as busy,” says Edelman.


Just don't do this

The most important thing to keep in mind when filing the extension—either by yourself, or through your preparer—is that an extension for completing your tax return is not the same as an extension for paying your taxes. This is where the danger of unknown fees lies.

Currently, the penalty for not filing taxes is 5% of the taxes owed, but if you file an extension, that clock won’t start until October 18. But meanwhile, even if you do file the extension, the fee for not paying starts on April 18th. It’s a smaller fee (only 0.5% of the taxes owed, calculated monthly), but that adds up if you’re not aware. Perhaps you see the problem with this arrangement.

“This creates a Catch-22,” says Edelman. “If you’re not preparing your return, how do you know how much tax you owe?”

This is where tax estimators come in handy. Edelman recommends simply finding what you paid last year and paying that, to at least put you in the ballpark of what you’d owe. There are also tax estimator calculators available online at the IRS website, or at H&R Block. But the key is don’t not pay anything.

“The worst thing you can do is be like, ‘hey, I think I owe a lot this year so I’m not going to do anything,’” says Pearlman. “It’s just making it worse if you ignore it.”

Pearlman concludes with some advice if you’re one of the brave souls filing at the last minute on your own. If you’re mailing your return, make sure you actually go to the physical post office and get a return receipt. (You can also file an extension online through or with your regular tax software.)

If you do go the post office route, “Don’t leave it up to chance with that mailbox on the corner,” she says. “Cover yourself.”

And, hey, on the way to and from the post office, you can look lovingly upon the sidewalks and roads that your tax dollars helped create.

Follow Rick on Twitter.