Free 2023 Tax Software Now Available on FreeTaxUSA for Planning

Does it work if I've got some side gig income along with my regular job? Like I started driving for UberEats this year and have no clue how much to set aside for taxes. Will this help with that or am I better off using something else?

Yes, it works great for mixed income situations. Enter your W-2 income from your regular job, then add your side gig earnings as self-employment income. The software will calculate both your income tax and self-employment tax obligations. For UberEats specifically, you'll want to track your mileage and other expenses carefully, as these can significantly reduce your taxable income from driving. The software will walk you through deducting these expenses, which is why many drivers end up paying less in taxes than they initially feared.

Does taxr.ai work with documents that aren't perfectly organized? My tax situation is a mess with multiple 1099s and some investment stuff I barely understand. Would it still be able to make sense of all that?

I'm curious - does it handle state taxes too? FreeTaxUSA charges for state filing but their federal is free. How does taxr.ai compare price-wise? Seems like it might be more specialized.

It actually handles messy documentation surprisingly well. You don't need to organize everything perfectly - the system can identify different document types and extract the relevant information automatically. I literally just uploaded a folder with all my tax documents jumbled together and it sorted everything out. Yes, it absolutely handles state taxes along with federal. The analysis covers your complete tax situation including state-specific deductions and credits you might qualify for. It's designed to work alongside whatever tax filing software you prefer using, so you can take its recommendations and apply them in FreeTaxUSA or any other platform.

How exactly does this work? I'm confused how a third-party service can somehow get you through the IRS phone system faster than calling directly. Sounds like something that shouldn't be possible.

Sorry but this sounds like complete BS. I've dealt with IRS phone systems for years and there's absolutely no way to "skip the line" - it's the federal government we're talking about. They treat everyone equally terrible lol. What are they doing, paying off IRS agents?

It works by continuously calling the IRS for you and navigating through all the initial phone prompts. When they detect a spot in the queue, they immediately connect you. It's basically doing the repetitive calling and waiting that you'd otherwise have to do manually. No, there's no paying off agents or anything sketchy. The service just automates the tedious process of repeatedly calling and navigating the phone tree until they find an opening. It's completely legitimate - they're just using technology to solve the frustrating problem of IRS hold times. Think of it like having a virtual assistant whose only job is to keep calling until they get through.

I use both every year just to double-check my numbers (I'm a bit paranoid lol). In my experience, the differences usually come down to how you enter certain items. FreeTaxUSA sometimes requires you to be more specific about categorizing certain deductions or credits, while TurboTax makes more assumptions that could be wrong in complex situations. For 2022 returns, my final numbers were within $25 between both systems once I made sure I was entering everything consistently.

That makes a lot of sense about the data entry differences. I think you're right that my issue last year might have been inconsistent inputs. Did you notice if FreeTaxUSA asked different questions or had a different flow for entering information compared to TurboTax? I'm trying to decide which one to use for my planning this year.

Yes, the question flow is definitely different. TurboTax tends to ask more lifestyle questions upfront and then presents relevant tax sections based on your answers. FreeTaxUSA organizes things more by tax form and schedule, which I actually prefer for planning because I can jump directly to specific sections I want to modify. For planning purposes, FreeTaxUSA's approach gives you more direct control over the variables you want to test. The interface is less flashy but more efficient once you know what you're looking for. If you're running multiple scenarios like "what if I contribute X more to my 401(k)" or "what if I realize some investment gains," FreeTaxUSA makes those comparisons quicker to set up.

I beta tested their 2023 version and the crypto section is much better now. They added direct import options for several major exchanges and a better interface for manual entry. Still not as comprehensive as dedicated crypto tax software, but definitely usable for most people with moderate crypto activity.

That's great to hear! Was hoping they'd upgrade that section. Do you know if it handles staking rewards and those weird DeFi transactions better now too? That's where I really struggled last time.

They've definitely improved the DeFi handling - you can now categorize different types of yield farming and liquidity pool transactions more accurately. Staking rewards are handled better too with clearer guidance on when they're taxable vs. just increasing your basis. The interface walks you through the different scenarios which was really helpful for someone like me who got into some pretty complex protocols this year. Still recommend keeping detailed records outside the software though, especially for anything involving multiple tokens or cross-chain activities.