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I literally just filed through H&R Block last week but used their DIY premium version for $55 instead of the $85 tax pro option. The software was super straightforward even with my 1099 income and some stock sales. It asked me all the right questions about my side gig and walked me through all possible deductions. Honestly if ur comfortable following instructions and have your docs organized, the DIY version might save you $30. It took me about 90 minutes total. The only reason I'd pay the extra for the tax pro version is if you're really uncertain about some complex situation or hate doing the data entry yourself.
I also used their DIY version but qualified for the free version. I owed a bunch though because I didn't have enough withheld from my paychecks. Would the tax pro version have helped with that or is that just my own fault for not adjusting my W-4?
That's really just about your W-4 withholdings, not which tax prep method you use. A tax pro might have mentioned that you should adjust your withholdings for next year, but they can't change what you already had withheld in 2024. If you want to avoid owing next year, you should fill out a new W-4 with your employer and either claim fewer dependents or request additional withholding. The DIY software actually should have given you a warning about this too and offered to help you calculate better withholding for 2025.
I've been in a similar situation and ended up going with the $85 H&R Block option last year. Overall it was decent value, but here's what I learned: The good: They did catch a few deductions I would have missed on my own, especially around my freelance work. The tax pro asked good questions about home office expenses and business mileage that I hadn't thought to track properly. The not-so-good: The whole process felt a bit impersonal since it's all done remotely. You upload everything and then get an email when it's ready to review. No real back-and-forth conversation unless you specifically reach out with questions. My advice: If you're organized with your documents and can clearly explain your side gig situation, it's probably worth the $85 for peace of mind. Just make sure to include detailed notes about your business expenses when you upload everything, and don't be afraid to ask questions if something doesn't look right on the draft they send you. For next year though, I'm thinking about trying one of the AI tax services people mentioned here - seems like they might be more thorough for complex situations.
Thanks for sharing your experience! That's really helpful to know about the impersonal nature of the remote process. I'm definitely someone who likes to ask questions as I go, so good to know I'd need to be proactive about reaching out. The AI tax services do sound intriguing based on what others have shared here. Do you think the $85 H&R Block option would still be worth it for someone doing this for the first time with a more complex situation, or would you recommend jumping straight to trying an AI service? I'm torn between going with something established vs. trying the newer technology.
Can I just say how messed up it is that a 20 year old has to deal with back taxes in the first place? The tax system is so complicated even for simple situations. The IRS should make things more clear about overpayments and just automatically refund money that's not owed without making people chase after it.
The system is definitely frustrating, but to be fair, they do automatically refund overpayments in most cases. The problem is their processing times are so slow, and the automated systems don't always work perfectly. When I overpaid my taxes 2 years ago, I got the refund without doing anything - it just took almost 3 months.
That's good to hear they eventually make it right, but 3 months is ridiculous for something that should be pretty simple to process. A 20-year-old might really need that money right now, not 3 months from now. I still think the whole system needs to be more transparent and user-friendly.
I completely understand your situation - dealing with back taxes at 20 is stressful enough without worrying about whether you'll get your overpayment back! The good news is that yes, the IRS will refund you that extra $50 (or however much you actually overpaid once they calculate everything). Here's what typically happens: The IRS will apply your $225 payment to your original tax debt, then to penalties, then to interest. Whatever's left over becomes a credit on your account that they'll automatically refund to you, usually within 6-8 weeks of processing your payment. Since you estimated high to be safe, you were actually being smart - it's better to overpay than underpay and get hit with additional penalties. Just keep an eye on your mailbox for either a refund check or a notice explaining how they applied your payment. If you don't hear anything after 8 weeks, that's when I'd recommend calling them to check on the status. The fact that you're being proactive about this at 20 shows good financial responsibility. Don't stress too much - you'll get your money back!
This is such a relief to read! I've been using Venmo to send my roommate about $1,200 monthly for rent and utilities for the past year and was getting really stressed about potential tax issues. One thing I'd add - if you're really paranoid like I was, you can keep a simple record of what each payment was for (like "March rent + utilities" in the memo). That way if anyone ever questions it, you have clear documentation that these were legitimate expense-sharing payments, not income or business transactions. Also appreciate everyone sharing their experiences with getting official confirmation from the IRS. It's so much better to have peace of mind than to worry about it until tax season!
That's really smart advice about keeping records in the memo! I just realized I've been super lazy with my payment descriptions - usually just put like "rent" or sometimes nothing at all. Going to start being more specific like "April rent share" or "utilities split" so there's no confusion later. Also totally agree about the peace of mind thing. I was literally losing sleep over this until I found this thread. It's crazy how something so simple can cause so much anxiety when you don't know the rules!
Thanks everyone for sharing your experiences! This thread has been incredibly helpful. I was getting really anxious about this whole situation, especially after hearing conflicting advice from friends and family. It sounds like the consensus is pretty clear - as long as we're just splitting legitimate living expenses and not making a profit, there's nothing to worry about tax-wise. The key seems to be making sure transactions are marked correctly as personal payments rather than goods/services. I think I'll start being more descriptive in my CashApp memos going forward (like "March rent share - $425" and "utilities split - $425") just to have a clear paper trail. Better safe than sorry! Really appreciate everyone taking the time to explain this. Tax stuff can be so confusing, and it's great to have a community where people share their real experiences and solutions.
This whole discussion has been such a lifesaver! I'm in a similar boat with three roommates and we've been using various apps to split everything - rent, utilities, groceries, you name it. I was starting to panic thinking we'd all have to report thousands in "income" that's really just us covering our fair share of living costs. The memo tip is genius - I'm definitely going to start being way more specific about what each payment is for. It's such a simple thing but could save so much headache if questions ever come up later. Thanks for starting this thread and getting everyone to share their experiences!
Just wanted to add my experience - I didn't get my W2 corrected last year (employer reported about $2,100 too much in wages) and I just filed with the correct numbers. Got a CP2000 notice about 6 months later questioning the discrepancy and had to go through the whole explanation process with documentation. Ultimately everything worked out fine, but it was a major headache that took multiple letters and a couple phone calls to resolve. Definitely would have been easier to just push for the W-2c upfront.
Did you end up having to pay any penalties or interest for the discrepancy? I'm in a similar situation now and wondering what to expect.
I actually just went through this exact situation a few months ago! My employer had incorrect withholding amounts on my W2 (about $800 difference) and I initially tried to just file with the correct numbers from my paystubs. Here's what I learned: Even though you can technically file with the correct information, you should absolutely request a W-2c from your employer. The IRS gets a copy of your original W2 directly from your employer, and when that doesn't match what you reported, it will almost certainly trigger a notice later. I ended up getting a CP2000 notice about 4 months after filing, which required me to respond with documentation proving the W2 was wrong. It was a hassle that could have been avoided if I had just pushed harder for the correction upfront. My advice: Contact your payroll department in writing (email works) and specifically request a "Form W-2c" to correct the errors. Reference the specific boxes that are wrong and include copies of your final paystub showing the correct amounts. If they don't respond within a reasonable time, you can contact the IRS at 800-829-1040 and they'll intervene on your behalf. The peace of mind of having matching documents is worth the extra effort!
This is really helpful advice! I'm curious - when you contacted the IRS at that number, were you able to get through easily or did you have to wait on hold for a long time? I've heard horror stories about trying to reach them by phone, but it sounds like having them intervene with your employer might be the best option if HR is being unresponsive. Also, do you know if there's a specific timeframe the IRS gives employers to issue the W-2c once they get involved? I'm wondering how long this whole process might take if I go that route.
Laura Lopez
Totally agree with filing the amendment. I went through this with forgotten stock sales in 2021. When I amended, I thought it would be a huge deal, but it was pretty painless. One tip: if you use tax software like TurboTax or H&R Block, they usually have an option to prepare an amended return based on your original filing. It makes the process WAY easier because they handle all the calculations and format everything correctly. Just make sure you print and mail the amendment - they can't be e-filed yet in most cases. And be prepared to wait a while for processing. Mine took about 4 months to get processed last year.
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Zane Hernandez
ā¢Thank you for the tip about using tax software for the amendment! I did use TurboTax for my original return so that would make it a lot easier. Did you have to pay again to use the amending feature or was it included with your original purchase?
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Laura Lopez
ā¢If you used the paid version of TurboTax, amending is usually included at no extra cost for the same tax year. You just log back into your account, select the return you want to amend, and there should be an option for "Amend return" somewhere in the menu. If you used the free version, you might have to pay to access the amendment feature, unfortunately. But even then, it's probably worth it for the convenience and accuracy. The system will walk you through exactly what changed and generate all the right forms.
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Zoe Alexopoulos
I'm a tax preparer and see this situation all the time - you're definitely not an idiot! Interest income reporting is one of the most commonly missed items. For $380 in interest, you're looking at maybe $40-95 in additional tax depending on your bracket. The IRS will eventually match your 1099-INT to your return through their automated system, but it can take 1-2 years. My professional recommendation: go ahead and amend. Here's why - if you amend voluntarily, you'll pay the tax plus minimal interest (calculated from the original due date). If they catch it first, you pay the same amounts PLUS potential penalties. The 1040-X isn't complicated for this type of correction. You'll just be adding the $380 to your income and recalculating your tax. Most tax software can handle this easily if you used it for your original return. One thing to keep in mind - make sure you have your 1099-INT form from the bank showing the exact amount. The IRS already has this information, so your amendment needs to match their records exactly.
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