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The best tax software for self-employed

Being self-employed is rewarding, but there are some caveats, one of which becomes more obvious at the end of each year — while you’re preparing to file your taxes. As an entrepreneur, and self-employed individual there’s a lot you must consider come tax time and the process is a lot different than doing a simple file. You have to keep track of your personal and business expenses and get your records in order, as well as review all of the tax deductions and credits, choosing what matches your experiences. At least, that’s the case if you do it all alone.

Of course, there are some alternatives. You can enlist the help of a tax professional, but that would mean printing all of your documents and bringing them into an office — or sharing the digital lot. You can also take advantage of the best tax software for self-employed professionals. These tools will guide you through the filing process and help you maximize your deductions and credits. The best part is you can stay home the entire time, or work from wherever your office is located. We’ve taken the time to research the best tax software, whether you’re a freelancer claiming some of your side gigs, or a small business owner claiming your profits for the quarter.

TurboTax Live Self-Employed

Intuit TurboTax Live tax expert on a virtual call.
Image used with permission by copyright holder
  • Federal: $199 | State: $37 per state
  • Start for free, pay when you file
  • Live help on-demand at no extra cost
  • Easy document import
  • Always get a final review with audit support

One of the more renowned tax filing services, and for good reason, is TurboTax. While they offer several editions to match your filing status, TurboTax Live Self-Employed is just what you need if you run your own business or venture. It is designed specifically for freelancers, independent contractors, and small business owners.

While you file, a real tax expert will help you, answering questions, ensuring you report the relevant work-related expenses, and they’ll also help you identify the best tax deductions. All of that help is on-demand, ready exactly when you need it, so you’re never alone and you always “have experts in your corner.” It’s less about peeking over your shoulder and more about well-informed guidance when you’re looking for it. Did we mention it all integrates with Quickbooks if that’s what you or your employer use to manage finances?

Before you file officially, your return will be reviewed one last time by an expert for accuracy and completion. If they notice something wrong, they’ll work with you to get it fixed, further reducing the potential for an IRS audit. Prices start at $199 for a Federal return, with additional fees for State taxes in select states, but you can file for free before February 15 for simple filers only. It’s hands down, the best option if you want a smooth filing experience and professional support especially since you can contact the experts anytime.

H&R Block Self-Employed Online

H&R Block offers self-employed tax filing support.
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  • Federal: $110 | State: $37 per state
  • Start for free, pay when you file
  • Live help is available separately ($145 and up)
  • Easy document import from competitors and more
  • Available on many devices, including mobile

H&R Block also provides several versions of its tax software tools, with Self-Employed Online being the titular option for entrepreneurs. Overall, the software makes it easy to file your taxes, keep track of documents, and tap into the optimal tax credits and deductions. You can connect external accounts to the service to import necessary documents. Filing is included, along with the tools to walk you through the entire process. What’s more, you can do the work from just about any device, be it desktop or mobile. It doesn’t matter where you’re doing your taxes, it’s always easy to fill in fields, get the help you need, or review your progress.

One thing to note about H&R Block is that if you want live help from a tax professional, you’ll need to pay for a higher tier, starting at $145, with an additional $37 for any state taxes filed. You can always ask questions without paying that fee, but for on-demand and live help, there’s no workaround. All in, however, H&R Block Self-Employed Online starts at $110, with an additional $37 per state filed. Guaranteed audit support is included for peace of mind. And when it comes to helping you file your taxes, H&R Block’s process is smooth, enjoyable, and definitely earns its place on our list.

Liberty Tax Premium

LibertyTax Premium for self-employed, freelancers, and contractors.
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  • Federal: $90 | State: $37 per state
  • Start for free, pay when you file
  • Virtual Tax Pro is available 24/7 for an added fee
  • Seamless filing between online and in-person
  • Audit assistance while filing

The sister company of Jackson Hewitt, Liberty Tax offers several filing tiers with Premium built for the self-employed, freelancers, contractors, or otherwise. Liberty Tax does offer its Virtual Tax Pro which connects you with a professional for guidance, questions, and more, but it will cost you extra. If you get stuck at any point while filing online, by yourself, you can transition seamlessly to an in-person office visit at a nearby Liberty Tax location. That makes this tool more valuable to anyone that thinks they might need to swap filing methods.

While filing, you can import documents from competitor services, and you’ll receive audit assistance, including help maximizing deductions and credits. The software experience is less intuitive than comparable options, but if you take things slow you shouldn’t run into any issues.

The full price for Premium starts at $90, but it’s usually discounted, with $37 additional per any state returns filed. Liberty Tax is a little more hands-off than some of the other options, but on-demand live support is available when you need it.

TaxSlayer Self-Employed

TaxSlayer mobile in use.
Image used with permission by copyright holder
  • Federal: $48 | State: $37 per state
  • Start for free, pay when you file
  • Customer support available
  • Easy document import for common forms
  • Long-term audit defense support

While the user interface does look and feel a bit dated, TaxSlayer Self-Employed still makes filing 1099 and W-2’s easier than ever. You can prepare, print, and e-file your taxes directly to the IRS. During the entire process, you’ll have access to digital support to maximize deductions. Though, unlike the premium services above, it’s easier to miss some of those deductions here, especially if you don’t understand what they’re for or what information you’re supposed to be providing. You can talk to a tax professional with self-employment filing expertise to share, although they’re not available on-demand. That simply means you might have to wait a little longer for a response.

You can start filing for free right away, and you’ll pay only when you officially file your return. Prices start at $48 with additional fees for state taxes where applicable. Getting started is quick and easy. Just log in to your free account, start entering your info, and the tool will guide you through the rest of the process. Audit defense support, with complete defense and legal representation, is available for up to 3 full years after filing. It’s one of the longest coverage options you’ll find, which is impressive in its own right.

FreeTax USA

FreeTax USA with free federal filing for all.
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  • Federal: Free | State: $15 per state
  • Start for free, pay when you file
  • Email and account messaging support
  • Easy document import from competitors and more
  • Unlimited amended returns with audit assist

As the name implies, FreeTax USA offers free filing for all federal returns including premium forms and IRS e-file services. State taxes cost $15 per file, on the other hand. While affordable, the experience is definitely not as intuitive as the premium tax tools. Everything is done from a browser, but you can access the service from desktop and mobile. Support is not always quick to respond. That said, customer support with live chat is available during the process and you do have access to knowledgeable professionals.

You can import documents, including past returns, from other software. That makes it faster when you’re importing old tax documents and the necessary forms for this year’s filing. During the process, your work will be checked and double-checked for inaccuracies to help reduce the chance of audits. There’s one final check before you officially file, as well, to catch any last-minute errors. There’s nothing in your way if you wanted to get started. Just log in, and begin entering the relevant information — it’s that easy. If you’re confident filing your taxes alone, and would like to save a little money, this is an excellent option.

While there are a ton options when it comes to filing your taxes as a business owner or self-employed individual, it’s important to remember that not all of them offer a convenient process. Everything on this list will certainly do that, and more. Most also offer on-demand or quick chat support when you have a question or run into a problem. Going above and beyond, and worth a call out, TurboTax Live makes it super easy to sync up with a tax expert, whenever you need. Of course, you can’t go wrong with any of the choices above.

Briley Kenney
Briley has been writing about consumer electronics and technology for over a decade. When he's not writing about deals for…
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