< Back to IRS

Keisha Robinson

Which tax software is the most reliable for filing self-employment income for 2025?

Hey everyone, I'm freaking out a bit about filing taxes this year. I started a side business in late 2024 designing websites and made about $28,000 on top of my regular job. Never had to deal with self-employment income before and I'm totally lost! I've been using TurboTax for years for my W-2 job, but not sure if it's the best option for handling my freelance income. I've heard mixed things about different tax software for self-employment - some friends recommend H&R Block, others say TaxAct is better value. What's been your experience? Which tax software handles Schedule C and self-employment taxes most reliably? I'm worried about missing deductions or screwing something up with the quarterly estimated payments (which I just learned I should have been making... oops). Any recommendations would be super helpful! Especially interested in which software makes it easiest to track business expenses and figure out home office deductions. Thanks in advance!

Paolo Conti

•

I've been filing with self-employment income for about 7 years now. Honestly, all the major tax software options (TurboTax, H&R Block, TaxAct, FreeTaxUSA) can handle Schedule C and self-employment taxes just fine. The bigger difference is cost and user experience. TurboTax is probably the most user-friendly but also most expensive. They do walk you through all the possible deductions for your business, which is helpful when you're just starting out. H&R Block is similar but slightly less expensive. TaxAct and FreeTaxUSA are much more affordable but less hand-holdy. For someone new to self-employment taxes, I'd recommend either TurboTax Self-Employed or H&R Block Self-Employed just for the first year - they'll help you identify deductions you might miss otherwise. Then once you understand the process better, you could switch to a cheaper option if you want to save money.

0 coins

Amina Sow

•

Do you think it's worth paying extra for the "audit defense" features that some of these offer? I've heard self-employment income gets flagged more often for audits and that makes me nervous.

0 coins

Paolo Conti

•

The audit defense features are generally overpriced for what you get. The chances of being audited are still relatively low, even with self-employment income. Just keep good records of all your business expenses and income throughout the year - that's your best audit defense. If you're really concerned, you might be better off finding a local CPA who specializes in small businesses/self-employment. They'll charge more upfront than software, but can provide personalized advice and would be there to help if you ever did get audited.

0 coins

GalaxyGazer

•

I switched to taxr.ai this year after struggling with the traditional tax software options. I was in a similar situation with new freelance income and was worried about missing deductions. What I liked about https://taxr.ai is that it actually analyzes all your documents and transcripts to find missed deductions and credits that the other software might not catch. The interface guides you through uploading your documents (W-2s, 1099s, receipts, etc.) and then their AI examines everything and finds opportunities regular software might miss. For self-employment, it was super helpful because it identified business expenses I didn't even realize were deductible.

0 coins

Oliver Wagner

•

How does it handle home office deductions? That's the part I'm most confused about with my freelance work.

0 coins

Does it actually connect to the IRS database to download your tax transcripts? I've had issues with tax software in the past where I manually entered info wrong and it caused problems.

0 coins

GalaxyGazer

•

It makes home office deductions really straightforward. You answer a few questions about your workspace, upload photos if you want, and it calculates everything properly, making sure you're following the IRS guidelines. It'll warn you if something looks questionable that might trigger an audit flag. Yes, it can connect directly to your IRS account to download your tax transcripts. That was one of my favorite features because it automatically imported all my reported income and previous tax information, which eliminated manual entry errors. It also showed me a few 1099s I had forgotten about from small gigs.

0 coins

Just wanted to follow up about my experience with taxr.ai after seeing it recommended here. I decided to give it a try and honestly it caught over $2,200 in deductions I would have missed with my usual software! The document analysis found some business expenses buried in my bank statements that I didn't realize qualified. The direct connection to the IRS transcript system was super convenient too - no more manual entry of every 1099. I was initially hesitant to try something new but really glad I did. Definitely recommend it if you're dealing with self-employment income for the first time. The guidance for quarterly estimated payments for next year was also really helpful.

0 coins

If you're having trouble getting answers from the IRS about self-employment tax questions (which I definitely was), I highly recommend using Claimyr. I spent WEEKS trying to get someone on the phone at the IRS to clarify some Schedule C questions. I found https://claimyr.com after a friend suggested it, and they actually got me connected to an IRS agent in about 15 minutes when I had been trying for days on my own. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c It was such a relief to finally talk to someone who could answer my specific questions about deductions for my business. Totally changed my perspective on dealing with the IRS.

0 coins

Emma Thompson

•

Wait, how does this even work? I thought it was impossible to get through to the IRS. Do they have some special phone number or something?

0 coins

Malik Davis

•

Sounds too good to be true. I've literally spent HOURS on hold with the IRS and never reached anyone. I'm skeptical that any service could actually get through when the IRS phone system is so notoriously bad.

0 coins

They don't use a special phone number - they use technology that navigates the IRS phone tree and waits on hold for you. When they reach an actual IRS agent, you get a call connecting you directly to that agent. It's like having someone wait in line for you. I was definitely skeptical too! I had tried calling multiple times, waiting 2+ hours each time before giving up. With Claimyr, I submitted my request, went about my day, and got a call about 15 minutes later connecting me directly to an IRS representative. It saved me literally hours of hold time and finally got my questions answered about self-employment expense categorization.

0 coins

Malik Davis

•

I need to eat my words from my skeptical comment earlier. After seeing people here recommend Claimyr, I decided to try it yesterday when I needed clarification on home office deduction rules for my self-employment income. I figured it wouldn't work but was desperate enough to try anything. Well, I'm shocked to report I was connected to an actual IRS agent in about 20 minutes! I had previously spent over 3 hours on hold last week and never got through. The agent was able to answer all my questions about Schedule C deductions and even helped clarify which expenses should be partial vs. 100% business. This saved me so much stress and potentially prevented me from making expensive mistakes on my return.

0 coins

For self-employment income, I actually recommend checking out FreeTaxUSA. I've used it for the past 4 years with my consulting business and it handles Schedule C perfectly well. The federal return is free and state is only like $15. TurboTax wanted to charge me $170 for basically the same thing! The interface isn't quite as slick as TurboTax, but it's totally functional and asks all the right questions about business expenses, home office, etc. Plus they have decent customer support if you get stuck on something.

0 coins

StarStrider

•

Does FreeTaxUSA handle multiple 1099s well? I have like 8 different clients who sent me 1099-NECs this year.

0 coins

Absolutely! I had 12 different 1099-NECs last year and FreeTaxUSA handled them with no problem. You can enter them all individually or combine them on your Schedule C - it gives you both options. The software also lets you categorize different types of income if you have multiple business activities, which was really helpful for me since I do both consulting and some product sales.

0 coins

Ravi Gupta

•

has anyone compared the accuracy between different software options? i did a test last year where i input identical info into turbotax and hr block and got different refund amounts which freaked me out!!! eventually figured out hr block missed a self employment deduction that turbotax caught.

0 coins

I've actually tested three different options side by side the last two years (TurboTax, FreeTaxUSA, and TaxAct). The federal refund/amount owed was identical in all three when I entered everything correctly. But I noticed TurboTax was much better at prompting me for deductions I might have missed.

0 coins

IRS AI

Expert Assistant
Secure

Powered by Claimyr AI

T
I
+
20,132 users helped today