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This might be a stupid question but... if I'm filing an extension, do I still need to contribute to my IRA by April 15th to count it for last year? Or does the extension give me until October for that too?
Not a stupid question at all! Unfortunately, the extension doesn't give you extra time for IRA contributions. The deadline for making IRA contributions for the previous tax year is still the original filing deadline (April 15th for most people), regardless of whether you file an extension. So if you want to make a contribution to count for 2023, you need to do it by April 15, 2024, even if you're filing an extension for your tax return.
Just wanted to add something that might help with your Form 4868 extension - since you mentioned getting a refund last year and having a similar financial situation, you're likely safe putting zero for the estimated tax liability. But if you want to be extra cautious, you could put a small amount like $100 just to avoid any potential issues. For the 8949 checkbox confusion, I had the same problem last year! The key thing to remember is that you MUST check one of the boxes - leaving it blank will cause processing delays. Most individual crypto traders end up using Box C (short-term, not reported on 1099-B) and Box F (long-term, not reported on 1099-B) since most exchanges don't provide proper 1099-B forms with cost basis information. One tip that saved me a lot of headaches: keep detailed records of all your transactions with dates, amounts, and what you paid for each crypto. Even if you use software to help calculate everything, having your own backup records is invaluable if the IRS ever has questions. Good luck with your extension!
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You need to use the EITC Assistant on the IRS website. With your income level and three qualifying children, you're looking at a significant Earned Income Credit. You should also claim the Child and Dependent Care Credit if you paid for childcare. Your refund will likely be substantial, but you need to file correctly. The self-employment tax will reduce it somewhat, but the credits should more than offset this. Consider making estimated tax payments next year to avoid any penalties.
Would this income level also qualify for the Additional Child Tax Credit if the regular Child Tax Credit exceeds their tax liability? I'm trying to understand if there's a phase-out that would apply here or if they'd get the full refundable portion.
What about the Recovery Rebate Credit? Or is that not applicable anymore for the current tax year? I'm still learning all these different credits and which ones are still available.
Based on your income levels, you're definitely in a good position for a substantial refund! With $19,000 total income and 3 qualifying children, here's what I'd expect: **Child Tax Credit**: $6,000 (3 kids × $2,000 each) **EITC**: Around $6,500+ with 3 kids at your income level **Self-Employment Tax**: ~$706 (as others mentioned) The key factors that will determine your exact refund: - How much was withheld from your W-2 (this is crucial!) - Your filing status (Head of Household vs. Married Filing Jointly makes a huge difference) - Whether you qualify for Additional Child Tax Credit if your credits exceed your tax liability Your income is low enough that you'll likely get most/all of these credits as refunds rather than just reducing tax owed. I'd estimate you're looking at $8,000-$10,000+ refund range, but definitely use the IRS EITC Assistant tool that Sara mentioned - it's the most accurate way to calculate the Earned Income Credit portion. Don't forget to keep receipts for those medical expenses too - they might be deductible if they exceed 7.5% of your AGI!
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Don't panic! I had the exact same issue with Cashapp and IDEX stock last year. If your total gain was only $340, then Cash App probably didn't meet the threshold for sending you a 1099-B. I called their support and they confirmed they only send forms if your trades exceed certain amounts. What I did was create my own makeshift "1099" using my transaction history from the app. I calculated: - Initial investment (purchase price × number of shares) - Final sale amount - The difference (my capital gain) Then I reported it on Form 8949 with Box C checked (for transactions without a 1099-B). The IRS never questioned it and my return was processed normally.
Thanks so much for sharing your experience! That's really reassuring to hear. Did you have to attach any supporting documentation from your Cash App account when you filed, or did you just fill out the form with your calculated numbers?
I just filled out the form with my calculated numbers, no need to attach the Cash App documentation to your tax return. However, I did save PDF screenshots of all my purchase and sale confirmations in case I ever get audited. The key is making sure your calculations are accurate. Double-check your math and be sure to include any fees in your cost basis. As long as you're reporting everything properly and paying the correct tax, the IRS is generally fine with self-reported stock transactions when a 1099 wasn't issued.
Quick tip from someone who works in tax prep - even if you don't receive a 1099, the IRS probably will. Financial institutions send copies of all 1099s to the IRS, even if they don't meet the threshold to send one to you. So definitely report your stock sales accurately!
Wait that's confusing. So Cash App might send the info to the IRS but not to the user? How are we supposed to match their numbers exactly if we don't see what they reported?
That's a great point! The reporting thresholds can be different for what gets sent to taxpayers versus what gets sent to the IRS. Generally, if you calculate your gains/losses using your actual transaction records (like the OP has with their purchase and sale confirmations), your numbers should match what the broker reports to the IRS. The key is to be as accurate as possible with your calculations. Use the exact purchase price, sale price, and dates from your account history. If there are any discrepancies later, having your original transaction records will help resolve them. The IRS understands that sometimes taxpayers need to self-report when they don't receive forms, as long as you're making a good faith effort to report accurately.
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Is this your first job out of college? Just wondering if maybe you're misreading your paystub. Most paystubs will SHOW both employer and employee portions of FICA/Medicare for informational purposes, but only the employee portion actually comes out of your check. The employer portion is just shown so you can see the total cost of employment.
This is a really good point. My company does this too - they show their contributions on my paystub but those amounts aren't actually being deducted from my pay. It's just showing what they're contributing on my behalf to be transparent about total compensation.
This is a great point to double-check! @Owen, can you clarify - are you looking at your actual gross earnings on your W-2 or year-end statement, or are you looking at what's displayed on your paystub? Many paystubs will show employer tax contributions in an "informational" section that doesn't actually reduce your take-home pay. The key is to look at your W-2 Box 1 (wages subject to federal income tax) and compare that to your contracted salary amount. If your W-2 shows less than your contracted $125,000 (minus only legitimate pre-tax deductions you elected), then you definitely have a problem. But if the employer taxes are just being displayed on your paystub for transparency without actually being deducted, your gross earnings should still match your contract. Can you check your actual W-2 and let us know what Box 1 shows?
This is exactly the right question to ask! I made a similar mistake when I first started working - I was looking at all the numbers on my paystub and getting confused about what was actually being deducted versus what was just informational. @Owen, definitely check your W-2 Box 1 first. If that matches your $125,000 salary (minus any pre-tax deductions you chose like health insurance or 401k), then the employer tax amounts you're seeing are probably just displayed for informational purposes and aren't actually reducing your pay. But if your W-2 Box 1 is significantly less than expected, then you've got a real issue that needs to be addressed with your employer immediately.
NeonNomad
Has anyone noticed if TurboTax is better or worse than other tax software for handling these 1099-B discrepancies? I'm having the same issue and wondering if switching to something else would help.
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Fatima Al-Hashemi
•I switched from TurboTax to H&R Block's software last year specifically for investment reporting and found it to be WAY more intuitive for handling complex 1099-B situations. Their interface for entering individual transactions made it much clearer when there were wash sales or other special situations.
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Chloe Green
I had this exact same issue with my 1099-B forms last year! The key thing that helped me was realizing that you need to look at the "Basis reported to IRS" checkbox on each form. If it's marked "No" (Box 3), then the broker didn't report your cost basis to the IRS, which means the simple math of proceeds minus cost basis won't match the net gain/loss they calculated. Also check if you have any transactions with adjustment codes in Box 1f - these can include things like return of capital distributions or stock splits that affect the basis calculation in ways that aren't immediately obvious from the main numbers. One more thing - if you're using the "summary" method in TurboTax where you just enter the totals, try switching to entering each transaction individually. It takes longer but gives the software all the detail it needs to properly handle the complexities. Good luck!
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