Ipiña Tax

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Every tax season, someone asks me the same question: “Which tax software should I use?” And honestly, the answer depends on you more than on the software.

I’m Francisco. I’ve prepared tax returns every season since 2022, and most of the people I work with are self-employed: rideshare drivers, house cleaners, contractors, freelancers. Some of them could absolutely file on their own with the right program. Others pay for an expensive tier they didn’t need, or pick a cheap one that leaves them guessing.

So instead of guessing, I sat down and ran the same self-employed return through six popular programs. Here’s what each one felt like to use, who I think it’s right for, and where I’d be careful.

My Picks at a Glance

Software	Best for	Last season’s price (federal / state)	Link
TurboTax Premium	Most guidance	Check site	Visit site
H&R Block Self-Employed	Human backup, in person	From $120 / $37	Visit site
FreeTaxUSA	Best value	$0 / $15.99	Visit site
TaxAct Self-Employed	Easy to follow	Check site	Visit site
TaxSlayer Self-Employed	Low price with tax pro access	$52.99 / $39.99	Visit site
Cash App Taxes	Completely free	$0 / $0	Visit site

Prices are from the 2026 filing season and can change during the season. New prices usually come out in December or January, and I’ll update this table when they do.

Before you pick any software, gather your paperwork. My free Tax Document Checklist lists every form and receipt a 1099 worker needs. (Versión en español.)

How I Tested

I tested all six during the 2026 filing season with the exact same sample return. I built it to look like the self-employed clients I see the most: one person, 1099 income, regular business expenses, and a good amount of driving.

While I worked through each program, I kept asking myself the questions my clients would care about:

• Does it explain things in plain language, or does it assume I already know which form I need?
• Does it ask about deductions, like mileage and supplies, or leave me to remember them?
• Can I finish without being pushed into a pricier version?
• If I get stuck, is there a real person I can ask?

1. TurboTax Premium: Best Overall Guidance

TurboTax Premium is TurboTax’s version for self-employed filers (it used to be called TurboTax Self-Employed). What stood out to me right away was how guided the whole process felt. It kept asking simple questions about my work, and those questions walked me through my deductions without me needing to know which tax form anything belonged on.

For someone filing a 1099 for the first time, that matters a lot. You don’t have to know what a Schedule C is. You just answer questions.

Where I’d be careful: the price. The experience was smooth, but if your return is simple, I have a hard time saying it’s worth paying TurboTax prices. And if you want a live expert to help you, that’s a separate, more expensive version (TurboTax Expert Assist).

My bottom line: the guidance is where TurboTax earns its place. If you’re nervous and want the software to lead you, this is the one.

2. H&R Block Self-Employed: Best Human Backup

I ran my sample Schedule C return through H&R Block’s Self-Employed version, with several common business expenses. The questions were straightforward, and I liked knowing I could get extra help if I got stuck.

To me, this felt like the middle ground between doing everything yourself and paying someone to do the whole return. And the in-person option is a real advantage. H&R Block has offices all over the country, so if you start online and get overwhelmed, you can walk in and talk to someone. For clients who get nervous doing taxes online, I think that peace of mind is worth a lot.

I’m not the only one who sees it that way: reviewers regularly point to its simple, step-by-step interface and easy access to tax pros.

Where I’d be careful: it gets expensive. Last season the Self-Employed version started around $120 for federal, plus $37 for state, and in-person help costs extra.

3. FreeTaxUSA: Best Value

This is the one that surprised me the most. I was able to complete almost my entire self-employed return without the software ever pressuring me to upgrade. Federal filing is free, and that includes self-employment income and Schedule C. State costs extra ($15.99 last season).

It isn’t as polished as the expensive options, and it won’t hold your hand as much. But if you keep good records and you’re comfortable typing in your own numbers, the value is hard to ignore.

My bottom line: if this isn’t your first year with a 1099 and you know your income and expenses, this is where I’d start.

4. TaxAct Self-Employed: Easy to Follow

TaxAct was easier than I expected. The questions were easy to follow, and I liked that it walked me through my information instead of dropping me into the tax forms.

It felt intuitive without being overly complicated. Customer reviews say the same thing: people often mention how easy it is to navigate.

Where I’d be careful: the same reviews include complaints about customer support, upgrade prompts, and the occasional technical problem. Before you file, double-check that your return actually shows as submitted.

5. TaxSlayer Self-Employed: Low Price, Mixed Reviews

With TaxSlayer, I focused on Schedule C income and deductions. The layout is fairly simple, and I could move through the return without much hand-holding. The price is one of the lowest of the paid options ($52.99 federal and $39.99 state last season), and the Self-Employed version includes access to tax pros with self-employment experience.

Where I’d be careful: the low price got my attention, so I paid closer attention to the help sections and the reviews. That’s where experiences are the most mixed. Some people love the interface and the support. Others report trouble with corrections, rejected returns, or a final charge that was higher than they expected. My advice: read every screen before you pay.

6. Cash App Taxes: Best Free Option

I tested Cash App Taxes with freelance income, and honestly, the first thing I noticed was how nice it was not to worry about an upgrade screen just to finish the return. Federal and state are both free.

If your situation is supported and you’re comfortable doing most of the work yourself, $0 is hard to beat.

Where I’d be careful: there’s no live support and no tax pro to call. You’ll type your 1099s in by hand, and you can’t file in more than one state. Whatever you enter, review every number yourself. Don’t assume the software caught everything.

Side-by-Side Comparison

Software	How guided it felt	Federal cost	Real person available?
TurboTax Premium	Very guided	Paid	Yes, in a pricier version
H&R Block Self-Employed	Clear and straightforward	Paid	Yes, online and in person
FreeTaxUSA	Light	Free	Limited
TaxAct Self-Employed	Easy to follow	Paid	Yes; mixed reviews
TaxSlayer Self-Employed	Simple layout	Paid	Yes; mixed reviews
Cash App Taxes	Do it yourself	Free	No

So, Which One Should You Use?

• It’s your first year with a 1099: TurboTax Premium or H&R Block. Pay for the guidance this one time; it’s worth it while you learn.
• You drive for Uber, Lyft, DoorDash, or Instacart: any program that asks about mileage, plus a good mileage tracker app so your numbers are ready before you sit down.
• You clean houses or do home services: FreeTaxUSA if you keep good records; H&R Block if you want someone to check your work.
• Money is tight: FreeTaxUSA or Cash App Taxes.
• You file with an ITIN: if you already have a valid ITIN, you can generally e-file with tax software. If you need a new ITIN or have to renew one, the return has to be mailed with Form W-7, so software alone won’t get you there. My ITIN guide explains how it works.

Deductions I Always Double-Check

Software only asks about what it’s programmed to ask about. Whatever you use, make sure you’ve thought about these:

• Mileage vs. actual car expenses: you can usually choose the standard mileage rate or your actual vehicle costs. What you choose the first year you use a car for business can limit your options later.
• Phone and internet: the business-use percentage is deductible.
• Supplies and equipment: cleaning supplies, tools, and phone mounts add up fast.
• Home office: only if you use the space regularly and only for business.
• Half of your self-employment tax: the software handles this one for you, and it lowers your income.

When Software Isn’t Enough

Software works for a lot of 1099 workers. But I’d talk to a tax preparer if:

• you owe back taxes or have years you didn’t file;
• you got a letter from the IRS;
• you or someone in your family needs a new or renewed ITIN;
• you have employees, inventory, or more than one business.

FAQ

Do I need to pay quarterly estimated taxes?

Generally, yes, if you expect to owe $1,000 or more for the year. Payments are usually due in April, June, September, and January.

Will I get a 1099-K from Uber, Lyft, or PayPal?

Payment apps and marketplaces generally send a 1099-K when you receive more than $20,000 across more than 200 transactions in a year. Rideshare companies may also send a 1099-NEC. Either way, all business income is taxable, whether or not you get a form.

Can I file with an ITIN using tax software?

If you already have a valid ITIN, generally yes: you enter it where the software asks for a Social Security number. If you need a new ITIN or are renewing one, you can’t e-file. The return must be mailed with Form W-7 or submitted through a Certifying Acceptance Agent.

What’s the cheapest way to file as self-employed?

Cash App Taxes (free federal and state) and FreeTaxUSA (free federal, low-cost state), as long as your return fits what they support.

About the author: Francisco is a tax preparer and IRS Certifying Acceptance Agent who has prepared returns since 2022. He works mostly with self-employed clients, gig workers, and ITIN filers, in English and Spanish.

This article is for general information only and isn’t tax advice for your specific situation. Features and prices change every season; check each provider’s site before you buy.