Tax day is April 18th—today. We shouldn’t have to be here, but here we are. Sure, you can labor through the labyrinthine official tax forms and send those to the U.S. government yourself. But as is the case every year in the U.S., the best options for less stress when filing taxes online for free are also the same services that have helped created this whole mess in the first place.
Companies are regularly trying to upsell you on tax filing services. Previous audits of major tax filing services found millions of U.S. citizens paid for services they could have gotten for free. Despite the intensified scrutiny, you’ll still see most major services employing dark patterns in the UI to emphasize paying for services that don’t benefit users.
Yes, you have to do something about your taxes. Yes, you might end up going through a website that’s trying to upsell you hard from their ‘free filing’ options. Yes, it will take you a good chunk of your free time.
In the end, you really have few options for stress-free filing. That’s why we’re here to give you some advice on how and where to file and what’s the best way to get an extension if you need one.
Where do I e-file?
Sites like TurboTax and H&R Block have a near stranglehold on the online tax filing market. The IRS has its own Free File sites listed, but most are awful. The IRS requires that these sites offer a free e-filing option, but there is no real regulation on how much these companies try to upsell you when filing, and no regulation about how well it presents information to users.
The IRS does not offer an in-house option to file based on a deal it struck with tax filing companies two decades ago. And despite advertising these free options, some of the IRS’ suggested sites, such as 1040NOW.net, have UI that would have looked dated a decade ago. These sites also have restrictions based on your adjusted yearly income, though most allow for filing if you make $73,000 per year or less. There may also be restrictions based on which state you live in. Some, like TaxAct’s free version, do not allow for the free filing of state taxes.
Notably, Intuit, the company behind TurboTax, announced back in 2021 that it was no longer participating in the U.S. Free File program. Despite the program being created to allow these companies to continue milking citizens when filing taxes, Intuit said it left because of “strict requirements concerning user experiences.” Similarly, H&R Block is also no longer a part of the Free File program.
All in all, if you’re set on using a free file program, then TaxSlayer might be your best option. You need to be 58 or younger making less than $73,000 a year, be eligible for the Earned Income Tax Credit, or be an active duty military servicemember making less than $73K. You also have to live in one of just 23 listed states—otherwise, it will cost upwards of $75 to file both state and federal returns.
You can also plug in all the numbers yourself using the IRS form-fillable documents, but that will require you to create an account on the IRS site, which itself can be quite a time-consuming hassle as it will require you to have an ID like a driver’s license or passport at the ready, and also scan your face to ID.ME. This is also the most lengthy option, and since it’s already Tax Day, you’re best either filing for an extension or using the other tax filing options.
TurboTax is often noted as the easiest-to-use e-file option. They have a lot of tooltips to help you find out which form to file and where to find the information the system needs. You can also simply upload your W-2 and it will fill out all the necessary boxes automatically. It also helps if you use them year after year, as some of your profile information gets saved. The catch is they also are notoriously predatory in how they try to upsell you, and despite their advertising the free offering, they are also one of the most expensive options if you get suckered into giving them money to file.
Other free options include:
- Cash App’s free service (which has been noted for upselling users)
- H&R Block Free Online
- Tax Slayer Simply Free
- TaxAct Free Edition
How do I get a tax extension?
Most of the free file options listed above also allow you to submit for an extension. You can log onto one of these sites and answer the questions to submit for the extension.
This is effectively an option for you to note your tax liability and then pay what you owe. The IRS will charge a 3% interest on the unpaid balance until the full amount gets submitted, and there will likely be further fees for every month they go unpaid.
This extension gives you until October 15 to file your taxes. You will need to note what you already paid on the extension when you file your taxes later this year.
If you don’t want to use those e-file platforms, you’ll need to submit a form to the IRS. Since it’s already Tax Day, your best option would be to file the form online through the e-file providers.
There is no penalty for filing the form last minute, but there can certainly be repercussions if you fail to file anything at all. You should receive a notification that the extension application has been filed. There are ways to track the status of your application as well.
What should I know about filing taxes this year?
Most people will not find things too different from last year. It’s already a little late for you to start considering recording mileage rates for a tax exemption, as those rates have increased. Most people will be filing for a standard deduction, which was adjusted for inflation to $12,950 for single or married separately, or $25,900 for anyone who is filing jointly or is a surviving spouse.
The federal government made several changes to clean vehicle credits and other deductions thanks to the 2022 Inflation Reduction Act. If you think you apply, it might be worth a quick study to get your mind around it.
Is AI becoming the new hotness for tax filings?
With all the hubbub about AI chatbots, of course the major tax filing companies are working on using large language models to speed up the filing process. There are a few new examples of companies that say they’re using AI systems to power their filing services, but just like the rest of the industry, they’re a mishmash of various monetizing schemes. At this point, it’s best to avoid any app that tries to use AI hype as its main selling point, especially as AI is fully capable of being completely wrong.
This year, H&R Block talked up technology that found missing refunds missed by TurboTax. Meanwhile, TurboTax is currently testing a so-called “Express Lane” for those working on relatively simple filings that could be finished in “10 minutes or less.” In an interview with Fast Company, Intuit VP Varun Krishna said it’s only being rolled out to existing TurboTax users, though in coming years the company wants it to become a bigger staple in its filing software.
TurboTax’s AI system is essentially a chatbot that wants to use natural language to file taxes compared to the current question-and-answer format. This new program is being explicitly targeted to “GenZ and Millenials.”
Both major tax-filing companies will likely push more AI-based services in the coming years. With it will come a bevy of other services following along on its heels.
You probably shouldn’t use a dating sim to file your taxes
Your options for digital tax filing now even include an anime-style dating sim. Created by Brooklyn-based art collective MSCHF, Tax Heaven 3000 is a game styled like any other rough dating sim you might find crawling through the bowels of Steam, but it actually asks the necessary questions for filing your taxes. By going on dates with the pink-haired anime girl named Iris, users can sort through their tax returns and tax credits, which then lets them print out the correct forms to send to the IRS.
The explicit point of the dating sim/tax service is to protest against the major tax services. MSCHF’s manifesto portion of their site says Intuit, the maker of TurboTax, “actively seeks to backdoor the regulatory structure that could otherwise seek to rein it in. And it works!”
Users need to download Tax Heaven directly from the store page, as the Steam version was delisted without any notice earlier this month. Though Valve has not responded to inquiries, the likely problem is users are being asked to submit sensitive personal info. The developers have claimed that Tax Heaven 3000 does not connect to the internet, though we can’t advise that anybody takes up an unknown program that asks for users’ ultra-sensitive data.
A last note
Just a reminder, the main reason that you’re stressing about taxes is that companies like Intuit and H&R Block have lobbied heavily to quash any mention of a return-free program, or even for the IRS to invest in its own free-file system.
So part of the reason we have this headache every year is that these large fintech companies are making too much money off the laborious nature of filing our taxes. Sorry for the downer, especially as you’ll likely be spending your lunch or evening today filling in last-minute forms.