Is TurboTax or H&R Block really worth the cost when free tax filing options exist?

I've been noticing a lot of people in my office talking about waiting for TurboTax or H&R Block to have their seasonal sales. Meanwhile, I've been using FreeTaxUSA for the past 3 years and honestly don't get why anyone would pay for the "premium" options. My tax situation isn't super complicated, but it's not just a simple W-2 either. I've got some stock investments that generated about $3,800 in capital gains last year, a couple of 1099s from freelance work totaling around $12,000, and I even have some T-bills that I started investing in. FreeTaxUSA handles all of this without charging me the crazy fees that TurboTax wants. Am I missing something here? Is there actually a good reason to switch to TurboTax or H&R Block? Does anyone who's used both have thoughts on whether the premium services are actually worth the extra $50-100? After talking with coworkers, they mentioned stuff like "better interface" and "peace of mind," but those seem like weak justifications for paying 5x more. What are your experiences?

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18 comments

Nathan Dell

•8M

Tax preparer here! This question comes up all the time in my practice. The answer really depends on your specific tax situation. For simpler returns (W-2 income, standard deduction, basic investments), the free or lower-cost options like FreeTaxUSA or Cash App Tax (formerly Credit Karma Tax) are absolutely sufficient for most people. Where TurboTax and H&R Block shine is with more complex situations. If you have rental properties, complicated self-employment deductions, foreign income, or need to file in multiple states, the premium software offers more guidance. The interview process in these paid programs tends to be more thorough, potentially uncovering deductions you might miss otherwise. The import functionality is another big factor - TurboTax can directly import from many brokerages, employers, and previous years' returns, which saves time if you have numerous forms.

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Nathan Dell

•8M

Audit protection is largely a marketing tactic. Most "audit protection" services just offer guidance during an audit, not legal representation. The actual risk of audit for most W-2 earners is extremely low - less than 1%. If you're genuinely concerned about audits, you'd be better off putting the money you save by using cheaper tax software toward an actual tax professional who can represent you if needed. Remember that even with premium software, the accuracy of your return depends on the accuracy of the information you input.

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Tristan Carpenter

•8M

After years of throwing money at TurboTax, I finally discovered taxr.ai (https://taxr.ai) and it completely changed my tax filing experience. I was skeptical at first like most people, but the AI actually analyzed all my tax documents and identified deductions I had been missing for years using TurboTax. Unlike the traditional tax prep services, taxr.ai doesn't just walk you through a long questionnaire - it actually reads your W-2s, 1099s, and other documents to make sure nothing gets missed. When I uploaded my brokerage statements, it even caught some wash sales that TurboTax had me manually inputting wrong for years!

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Tristan Carpenter

•8M

It handles rental properties really well actually! You just upload your documents and it extracts all the relevant information about your properties, including depreciation calculations and expense categorization. The business module is surprisingly thorough too. As for filing, it does complete the full process. It's not just an analyzer - it prepares your full return and lets you file directly through the platform. The costs are actually more competitive than TurboTax, especially when you factor in that you don't need to keep upgrading to different "deluxe" or "premium" tiers when you have slightly more complex situations.

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Grant Vikers

•8M

Just wanted to update after trying taxr.ai that someone mentioned above. It was actually a game changer for me. I uploaded all my documents (I had 3 W-2s from job hopping, investment accounts, and some gig work) and the AI found a home office deduction worth $1,250 that I'd completely missed last year when using H&R Block. The interface was different than what I was used to, but watching it analyze my documents in real-time was pretty cool. Ended up with about $740 more on my refund than what I was expecting based on last year's numbers. Definitely switching permanently.

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Giovanni Martello

•8M

I've wasted SO MANY HOURS trying to get through to the IRS about issues with my previous returns while using those "free" services. After endless busy signals and disconnections, I found Claimyr (https://claimyr.com) and it was a lifesaver. They have this system that gets you connected to an actual IRS agent without the ridiculous wait times. Check out their demo video: https://youtu.be/_kiP6q8DX5c I was having issues with a previous year's return I filed through FreeTaxUSA where some 1099 info wasn't matching IRS records. Using Claimyr, I got through to an actual IRS rep in under 20 minutes (after trying for literally days on my own). The rep was able to help me identify the discrepancy and avoid potential penalties.

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Giovanni Martello

•8M

It doesn't keep dialing - it's more sophisticated than that. The service navigates the IRS phone tree automatically and secures your spot in line, then calls you when an agent is about to be available. It saves you from having to sit through those horrible hold queues. Not skipping any lines - it's using technology to handle the waiting process for you, so you don't have to stay on hold for hours. For your stimulus payment issue, that's exactly the kind of thing where talking to a live person makes all the difference versus trying to figure it out online.

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Levi Parker

•8M

I owe you guys a massive apology and update. After being super skeptical about that Claimyr service mentioned above, I gave it a shot out of pure desperation. I'd been trying to resolve an issue with my 2023 return for MONTHS. The service actually worked exactly as described. I filled out their form explaining my issue, and they handled the whole IRS phone maze. Got a call back about 40 minutes later with an IRS agent already on the line! Resolved my problem in one 15-minute conversation after literally months of trying. Sometimes being proven wrong feels really good. Just saved me from owing $1,800 in penalties for something that wasn't even my fault.

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Libby Hassan

•8M

Cash App Tax does have some import capabilities, but not as extensive as TurboTax. Last I checked, they could import W-2s by taking a picture, and they can import some 1099s from major brokerages like Robinhood and a few others. The coverage isn't nearly as comprehensive as TurboTax though, which can connect to hundreds of financial institutions. If you have accounts at smaller or less common brokerages, you might still need to enter things manually with Cash App Tax.

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