15 Free Tax Filing Options for 2025 - Complete Guide with Self-Employment Support

I tried using Cash App Taxes last year but got really confused with how to enter my Doordash expenses. It seemed to accept the 1099 fine but when I tried adding mileage and other deductions, I couldn't figure out where they went. Do they have good support if you get stuck?

Cash App Taxes does have a slightly different flow for entering business expenses. When you enter your 1099-NEC, look for the "Business Income and Expenses" section - you'll need to create a Schedule C there. All your mileage and other deductions get entered in that section rather than as general deductions. They offer email support which is decent but can take 1-2 days to respond during peak season. Their help articles are actually quite good though - search specifically for "Schedule C expenses" in their help section and it walks you through the exact screens.

How does it handle multiple side hustles? I drive for Uber on weekends but also sell handmade stuff on Etsy and sometimes do TaskRabbit. Would I need to create separate accounts for each business or can it tell the difference?

Sounds interesting but I'm always worried about sharing financial documents with new websites. How secure is it? Do real people look at your documents or is it all AI processing?

For multiple side hustles, it actually handles them really well. You don't need separate accounts - you just tag different receipts/transactions for different business activities during the review process. The system recognizes patterns too, so after a while it automatically suggests the right business for each expense. Security is definitely solid. They use bank-level encryption for all documents. It's mostly AI doing the processing - no humans review your actual financial documents unless you specifically request help with something. They explained that even then, the support team only sees the specific item you're asking about, not your entire financial history.

How does that even work? The IRS phone system is a nightmare - I spent literally 3 hours on hold last year before giving up. Are you saying this service somehow gets through the queue faster?

Sounds like a scam tbh. Nobody can magically get through to the IRS faster than the regular line. They probably just connect you to some random "tax expert" who isn't actually with the IRS.

It doesn't get you through any faster than the regular line. What it does is handle the waiting for you. Their system calls the IRS, navigates through all the phone prompts, and then waits on hold in your place. When an actual IRS agent picks up, that's when they call your phone and connect you directly to that agent. It's definitely the real IRS. I was connected to an official IRS customer service rep who verified my identity with my tax ID number and previous filing details before answering my questions. Nothing sketchy at all - they just solved the problem of having to personally wait on hold for hours. Check out that YouTube video I linked if you want to see exactly how the process works.

Thanks for mentioning FreeTaxUSA! I've heard good things but haven't personally tried it. Does it handle cryptocurrency trading well? That's an area where I've seen some of the free options struggle.

FreeTaxUSA actually does handle crypto pretty well now. They added a much more streamlined section for it last year. It asks if you have a summary report from your exchange (like Coinbase) that you can import, or you can enter transactions manually. For mining or staking income, they have specific sections for those too, which categorize everything correctly for tax purposes. Definitely better than when I tried using TurboTax's free version for crypto a few years ago and got hit with an upgrade prompt.

For your situation with W-2 plus a single Airbnb rental, Cash App Taxes should work great - they support Schedule E for rental income at no charge. Just make sure you have all your rental income and expense records organized beforehand. FreeTaxUSA (mentioned in another comment) would also work - federal filing is free with rental income, though you'd pay $15 for state filing. The one caveat is if your rental situation is very complex (like multiple properties or partial business use), then you might still want professional help. But for a single Airbnb room, the free options should be perfectly adequate!

Thank you! That will save me a ton of money. I only have the one room I rent out so it's pretty straightforward. I'll definitely try Cash App Taxes this year instead of paying TurboTax's ridiculous fees.