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CosmicCrusader

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Have you considered TurboTax instead? I know nobody wants to switch software mid-return, but I successfully filed Form 8919 through them last year. Their interface walks you through the misclassification situation pretty clearly. They have specific questions that help determine if you qualify. Might be worth the switch if you're hitting roadblocks with FreeTax USA.

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Thanks for the suggestion, but I'm pretty deep into my return on FreeTax USA already. Did TurboTax also explain how to handle the SS-8 form? And did you end up getting a determination from the IRS about your worker status?

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CosmicCrusader

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TurboTax handled the 8919 form but like others mentioned, the SS-8 is filed separately regardless of which software you use. They do provide guidance about it though. I did eventually get a determination from the IRS, but it took almost 8 months. The good news is they ruled in my favor and determined I was an employee. My former company had to pay the employer portion of the taxes. Just be prepared for a long wait - the SS-8 process isn't quick, but filing Form 8919 with reason code G protects you in the meantime.

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Ethan Brown

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One thing nobody's mentioned - be prepared for potential fallout with your employer. When you file these forms, the IRS will eventually contact them as part of the determination process. Some employers don't take kindly to being reported for misclassification. Happened to me last year and it got awkward fast.

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Yuki Yamamoto

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This is really important advice. My friend filed SS-8 and not only did it create tension, but the company actually tried to retroactively create documentation to make it look like he was properly classified as a contractor. Make sure you have copies of all relevant emails, texts, schedules, etc. BEFORE you file!

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I hadn't even thought about that aspect. Thankfully I don't work for them anymore, but I still need references from them. Do you think I should give them a heads up before filing, or would that just create problems sooner?

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Sarah Jones

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I filed on January 29th and STILL haven't gotten my refund!!! The IRS Where's My Refund tool just says "still processing" for over 7 weeks now. I claimed the Child Tax Credit for my two kids. Anyone else waiting this long with CTC? Getting really frustrated!!

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Sebastian Scott

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I claimed CTC for my kids too and got my refund after about 4 weeks. Did you also claim Earned Income Credit? That usually takes longer. You might want to try getting your tax transcript from the IRS website - sometimes it shows more details about what's happening with your return.

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Emily Sanjay

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For those interested in extremely detailed stats: - E-filed with FreeTaxUSA on Jan 31 at 7:32pm EST - IRS acceptance email received Feb 1 at 9:14am - WMR updated to "approved" on Feb 15 - Direct deposit hit my bank Feb 17 at 3:42am Federal refund: $2,341 State refund: Still waiting, shows "processing" on state website Our return included W-2 income, 1099-INT, mortgage interest deduction, student loan interest, and HSA contributions. No tax credits. I've been tracking this data for years and this was about 3 days faster than last year!

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Jordan Walker

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You're even more detail oriented than me lol! Have you always used FreeTaxUSA? I've been thinking about switching from TurboTax to save some money.

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Emily Sanjay

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I've used FreeTaxUSA for the last three years after switching from TurboTax. The interface isn't quite as polished, but it's completely adequate and handles all my tax situations correctly. The federal filing is free and state is only $15 compared to the $120+ I was paying with TurboTax for the same exact results. If you have a fairly straightforward tax situation (even with some common deductions and forms like I listed), it works great. The only people who might want to stick with the more expensive options are those with extremely complex situations like multiple businesses, complex investments, or unusual tax situations.

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Jacob Smithson

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Another thing to consider - if either of you has previous tax debts or is behind on certain government payments (like child support), filing jointly could put the refund at risk. When you file jointly, your entire refund could be seized to pay those debts even if they only belong to one spouse. You'd need to file an injured spouse form to try getting your portion back, which is a hassle.

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Isabella Brown

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Do student loans fall into this category? If your spouse has defaulted federal student loans, will they take your refund if you file jointly?

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Jacob Smithson

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Yes, defaulted federal student loans can definitely lead to tax refund offsets. If your spouse has defaulted loans and you file jointly, the entire refund could be seized to repay those loans. Filing Form 8379 (Injured Spouse Allocation) can help you get your portion of the refund back, but it adds complexity and delays your refund by several months. If the student loans are in good standing or on an income-driven repayment plan, then you don't have to worry about refund offsets - it's only for defaulted loans. This is actually another situation where filing separately might make sense if one spouse has defaulted loans, as it protects the other spouse's refund entirely.

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Maya Patel

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First time my husband and I filed together, we tried both options in TurboTax and found filing jointly saved us almost $2,000! But everyone's situation is different. When one spouse is a student, joint is usually better because you can claim education credits on a joint return. Consider running your numbers both ways before deciding.

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Which tax software did you find easiest to use for comparing both options? I tried H&R Block online but it was confusing to switch between filing statuses to compare.

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Ingrid Larsson

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For last-minute tax reduction strategies, don't forget about 529 plan contributions! Many states offer tax deductions for contributions to these college savings plans, even if you open and fund one on December 31st. For example, my state (NY) allows deductions up to $5,000 per year for individuals or $10,000 for married couples filing jointly. You can name yourself as beneficiary if you don't have kids yet, and later change it. Just check your state's rules since not all states offer deductions.

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CaptainAwesome

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Does contributing to a 529 reduce federal taxes though? I thought it was only state tax deductions in some states. We're really trying to minimize our federal tax bill since that's where the big surprise is coming from.

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Ingrid Larsson

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You're right - 529 contributions don't reduce your federal tax bill, only state taxes in states that offer the deduction. I should have been clearer about that. While this won't help with your federal tax surprise, it could still save you some money on state taxes depending where you live. For federal tax reduction, your options before year-end are more limited since you've already maxed your HSA. If you own a business or have any self-employment income, you could potentially make SEP IRA or Solo 401k contributions, which would reduce federal taxable income.

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Carlos Mendoza

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Strongly recommend reviewing your W-4 withholding ASAP to prevent this problem next year. The 2020+ version of Form W-4 doesn't use allowances anymore, so if you're still thinking in terms of "0 allowances" you might be using outdated forms or concepts. The new W-4 requires you to account for multiple jobs and specifically address additional income like investment earnings. There's a whole worksheet for this now. Your Roth conversion definitely needed adjustment on your W-4.

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Zainab Mahmoud

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Yeah the new W-4 is actually way better for two-income households. My wife and I fixed our underwithholding problem by properly filling out Step 2 of the form. The old allowances system was garbage for dual income families.

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Best tax software for 1099 contractors with self-employed 401k contributions?

So I just went from being fully W2 to taking on contract work as a 1099 last year, and my taxes got way more complicated. My spouse still has a regular W2 job and we've been filing jointly through TurboTax since 2019, but this year was a nightmare. The biggest headache was dealing with my self-employed 401k. I set one up and made contributions as both "employee" and "employer" (since I'm technically both), but TurboTax kept rejecting anything above the $23k employee limit. It wouldn't recognize my employer contributions at all! I ended up having to date some contributions for 2025 instead just to get the system to accept them, even though I made them in January 2025 and could have applied them to either 2024 or 2025. Then there was the mileage tracking disaster. Every time I tried to enter my business mileage, the software kept bouncing me to some completely unrelated section. When I called support, they just told me I needed to "talk to a tax professional" even though it was clearly a software glitch. I didn't have tons of miles to claim, so I just gave up on that deduction for simplicity's sake. I'm already dreading next year's taxes and wondering if there's better software out there for our situation. We've heard about FreeTaxUSA but not sure if it handles 1099 contractor situations with self-employed retirement accounts any better. Any recommendations for tax software that actually works for self-employed folks with SE 401ks?

I've been self-employed for about 7 years now and have tried most of the major tax software. For 1099 income with retirement accounts, I've found TaxSlayer to be surprisingly good, especially for the price point. It handles self-employed 401k contributions correctly, separating employee and employer portions without the glitches you mentioned. The business mileage tracking is straightforward, and it lets you import from mileage tracker apps if you use those. Their support is also more knowledgeable about self-employment issues than H&R Block's in my experience.

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GamerGirl99

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Thanks for the TaxSlayer recommendation! How does it compare to FreeTaxUSA price-wise? And does it handle state filing too, or is that an extra charge?

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TaxSlayer is slightly more expensive than FreeTaxUSA for the self-employed version, but still much cheaper than TurboTax or H&R Block. Last time I used it, the federal filing with self-employment was around $55, and state filing was an additional $35 per state. State filing is indeed an extra charge with TaxSlayer, similar to most tax software except for the truly free options that have significant limitations for self-employed people. The state module is comprehensive though and handles all the specific state deductions and credits relevant to self-employment income.

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PixelPrincess

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I switched from TurboTax to FreeTaxUSA last year for my 1099 work and solo 401k, and I'm never going back! The solo 401k was handled perfectly with clear sections for both employee and employer contributions. One thing nobody's mentioned yet that I found super helpful was the comprehensive audit assistance. Since 1099 workers get audited more frequently, I liked having that extra protection. And the customer service was shockingly responsive when I had questions - got answers within hours instead of days.

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Omar Farouk

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Did you find FreeTaxUSA easy to navigate for business expenses? I do photography as a side hustle and have a ton of different expense categories. TurboTax makes it so complicated I'm afraid I'm missing deductions.

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