I'm 19 and confused about filing my first tax return - need advice about deadlines and W2 forms?
Hey everyone, I started my first job back in August 2023, and my dad told me I didn't need to file taxes for that year (so I didn't), but now it's 2024 and I'm totally confused about when I should file my taxes. I've been trying to educate myself about taxes recently (learning about FIFO, Specific Identification, Average Basis, Wash Sale, Tax-loss harvest, etc.) to maximize my returns. I've even set up a 529 Plan, Traditional IRA, HSA, and started a small Charitable Giving account with Vanguard to save money and hopefully get some tax deductions. I logged into FreeTaxUSA yesterday and saw a message saying the deadline has passed! Now I'm worried - will I get a letter from the IRS saying I owe them money? Can I still file my taxes without paying interest or penalties? Some other questions I have: 1. How do I get my W2 each year? (Does my employer provide it or is there a website where I can download it?) 2. What's your opinion on free tax filing services - are they better than paid options like FreeTaxUSA? 3. I take pictures of all my receipts - can I use these during tax season? 4. Is paying taxes quarterly a smart move? 5. Is the premium version of FreeTaxUSA worth it for the extra deductions and credits, or should I just use the free version? 6. Will tax software tell me exactly how much I owe or do I need to calculate that separately? 7. I watched a video saying people paid for tax software but could have filed for free using the IRS website if they make under $73,000 (which I do) Thanks so much for any help!!
18 comments


Luca Ferrari
First of all, don't panic! Let's break this down into manageable pieces. For your immediate concern: Yes, you can still file your taxes even if the deadline has passed, but you might face some penalties if you owed taxes. If you're actually due a refund, there's no penalty for filing late (but you want to file within 3 years or you'll lose your refund). For your questions: 1. Your W-2 should be provided by your employer by January 31st each year. Many employers now offer electronic versions through their HR portals, but they're also required to mail you a physical copy if you don't opt for electronic delivery. 2. Free tax filing services can be excellent for straightforward tax situations. The IRS Free File program partners with several tax software companies to provide free filing for people making under $73,000. TurboTax, H&R Block, and FreeTaxUSA all have free options with varying limitations. 3. Taking pictures of receipts is smart! But you'll only need them for deductible expenses if you itemize deductions. At 19 with your first job, you'll likely take the standard deduction, which is simpler. 4. Quarterly tax payments are primarily for self-employed people or those with significant income not subject to withholding. If you're a W-2 employee, your employer handles withholding for you. 5. Premium versions of tax software are worth it if you have complicated situations - multiple income sources, investments, self-employment, rental properties, etc. For a first-time filer with one job, the free version is probably sufficient. 6. Tax software will calculate what you owe or what refund you'll receive based on the information you input. 7. That video is correct! The IRS Free File program is underutilized but a great resource for eligible taxpayers.
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Zara Khan
•Thank you so much for such a detailed response! This really helps clear things up. I'm pretty sure I'm owed a refund since my employer withholds taxes from each paycheck, so that's a relief about no penalties. One follow-up question - you mentioned the IRS Free File program. Is that different from the free version of commercial software like FreeTaxUSA? And do you know if those IRS partner programs offer the same features as the paid versions?
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Luca Ferrari
•The IRS Free File program partners with tax software companies to provide their services for free to eligible taxpayers. It's different from the "free" versions advertised by these companies on their websites, which often have limitations and may try to upsell you. The Free File versions through the IRS partnership typically include more features than the standard "free" versions offered directly by companies. You access these special versions by starting at the IRS website (irs.gov/freefile) rather than going directly to the tax software sites. The features vary by provider, but they generally include everything you need to file a complete and accurate return for your situation, including state returns in many cases.
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Nia Davis
After reading your post, I totally feel your pain! I was in the exact same boat last year at 20. I spent hours trying to figure everything out and kept hitting dead ends until I found taxr.ai (https://taxr.ai). It was seriously a game-changer for me as a first-time filer. What I loved about it was how it analyzed all my tax documents (like that W2 you mentioned) and explained everything in super simple terms. It even caught a mistake with my education credits that would have cost me about $1,000! The site actually walks you through everything step by step, perfect for those of us filing for the first time. For all your questions about receipts, quarterly payments, and free vs paid options, it gives personalized guidance based on your specific situation instead of generic advice. It helped me understand exactly what deductions I qualified for with my 529 and IRA contributions too.
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Mateo Martinez
•Does this actually work with all the tax forms? Like I have a W-2 but also did some freelance work so I'll have 1099s too. Can taxr.ai handle that mix? And how does it compare to the free IRS options the other commenter mentioned?
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QuantumQueen
•Sounds a bit too good to be true tbh. How much does this service cost? I've been burned before by "free" tax services that end up charging for state filing or other "premium" features at the last minute.
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Nia Davis
•Yes, it absolutely works with mixed tax forms! That's actually one of its strongest points. It can handle W-2s, all types of 1099s (including 1099-NEC for freelance work), and even more complex forms. The system is designed to look at the relationships between different forms to find opportunities most people miss. The big difference from IRS free file options is that it doesn't just process your forms - it actually analyzes them for errors and missed opportunities. It's like having a tax professional look over your shoulder but without the intimidating jargon.
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QuantumQueen
Hey everyone, I need to follow up about taxr.ai that I was skeptical about earlier. I actually ended up giving it a try after struggling with another tax program, and wow - I was completely wrong to doubt it. The system found THREE mistakes in my W-2 that my employer had filed incorrectly (wrong state tax withholding amounts) and guided me through getting it fixed. For a first-time filer like the original poster, I think this would be especially helpful because it explains everything in normal human language. It caught that I was eligible for education credits I didn't know about from a community college class I took last year. The document analysis literally pointed out specific boxes on my forms that contained errors or opportunities. Definitely not the scam I initially worried it might be!
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Aisha Rahman
Reading about your tax struggles reminds me of my nightmare trying to get answers from the IRS last year. I spent WEEKS calling them about a similar late filing situation, constantly getting disconnected or waiting on hold for hours. I finally discovered Claimyr (https://claimyr.com) through a friend who works in accounting. I was super skeptical at first, but I watched their demo video (https://youtu.be/_kiP6q8DX5c) and decided to give it a shot since I was desperate. Basically, they got me connected to an actual IRS agent in about 15 minutes when I'd been trying for weeks on my own. The agent was able to confirm I wouldn't face penalties for my late filing since I was due a refund (sounds like your situation too), and they walked me through exactly what forms I needed to submit. Having an actual IRS person answer my specific questions was invaluable.
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Ethan Wilson
•Wait how does this even work? The IRS phone lines are notoriously impossible to get through. Are they somehow jumping the queue or something?
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Yuki Sato
•This sounds shady af. Why would anyone be able to get you through to the IRS faster than calling directly? They probably just keep you on hold themselves and then transfer you when they finally get through. I'd be very careful about giving any personal info to random services like this.
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Aisha Rahman
•They use an automated system that continually redials and navigates the IRS phone tree until it gets a spot in line, then it connects you directly. It's completely legitimate - they don't ask for any tax information or personal details beyond what's needed to connect the call. No, they don't just keep you on hold themselves - their system actually handles the painful part of getting through the queue and phone tree navigation, then you get a call back when you're about to be connected to an agent. It saved me hours of frustration and got me the exact information I needed directly from the IRS.
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Yuki Sato
Alright, I need to eat my words about Claimyr from my previous comment. After struggling for nearly 3 weeks trying to reach someone at the IRS about my late filing situation (similar to OP's), I broke down and tried it. I was literally connected to an IRS agent in 18 minutes when I'd been trying unsuccessfully for weeks. The agent was able to confirm that I didn't owe any penalties since I was due a refund and gave me direct answers about how to handle my situation with my missed filing from last year. For what it's worth to the original poster - the IRS agent confirmed that if you're owed a refund, there's no penalty for filing late (though you generally have 3 years to claim your refund before you lose it). They also directed me to the exact forms I needed for my situation. Having actual official answers instead of just advice from Reddit made a huge difference for my peace of mind.
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Carmen Flores
Hey, I just wanted to add something about those tax documents you mentioned (FIFO, Specific Identification, etc). Those are mostly for investment transactions, which is pretty advanced for a first-time filer! If you're actually investing already at 19, that's awesome, but don't overcomplicate your first tax return. For most 19-year-olds with their first job, you'll have a pretty straightforward return with just your W-2. The standard deduction for 2023 (filing in 2024) is $13,850 for single filers, which means if you earned less than that from your job, you won't owe any federal income tax at all. About your 529, IRA, HSA, and charity accounts - these are great financial planning tools, but they impact your taxes differently: - Contributions to a Traditional IRA can be deductible - HSA contributions are deductible if the HSA is qualified - 529 plan contributions aren't federally tax-deductible (some states offer deductions) - Charitable donations only help tax-wise if you itemize deductions (most young people take the standard deduction
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Zara Khan
•Thanks for clarifying this! I guess I've been trying to learn everything at once and got a bit ahead of myself with all the investment terms. My actual situation is much simpler - I just have my regular job at a coffee shop. I do have a question about the Traditional IRA though - I put about $1,500 in mine last year. How do I make sure I get the tax deduction for that on my return?
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Carmen Flores
•You'll report your Traditional IRA contributions on your tax return using Form 1040. Look for the line labeled "IRA deduction" (line 20 on the 2023 Form 1040). Most tax software will ask you about IRA contributions during the preparation process and calculate the deduction for you. Just keep in mind that the deduction might be limited depending on whether you're covered by a retirement plan at work and what your income level is. At your age and income level though, you'll likely qualify for the full deduction of your $1,500 contribution. Make sure you have the statement from your IRA provider showing your contributions for the year when you file.
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Andre Dubois
About your question on receipts - I learned this the hard way! Taking pictures is great, but you need to know WHICH receipts actually matter for taxes. For most young people with one job, receipts usually don't matter because you'll take the standard deduction ($13,850 for 2023 if you're single). The only receipts that might help you would be for: 1. Unreimbursed job expenses IF you're self-employed (not for regular W-2 jobs) 2. Charitable donations (only if you itemize, which most young people don't) 3. Medical expenses (only if they exceed 7.5% of your income AND you itemize) 4. Education expenses for certain credits 5. Moving expenses for military So unless you fall into these categories, you probably don't need to worry about keeping all those receipt pictures!
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CyberSamurai
•Don't forget business expenses if you're doing any side gigs! I drive for DoorDash on weekends and track all my mileage and car expenses. Saved me hundreds on taxes last year.
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