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Im in a similar situation but my numbers are different - my line 15 is -2,453 and line 16 is 3,102. I put the -2,453 on line 3 of the worksheet but then tax software is giving me an error saying I cant have a negative number there?? So confused.
Just a heads up - make sure you're using the correct worksheet version for your tax year. The Qualified Dividends and Capital Gain Tax Worksheet gets updated, and using last year's version could lead to errors. I learned this the hard way when I was using old instructions I printed out last year. Also double-check that you correctly calculated lines 15 and 16 on Schedule D in the first place. Line 15 should be your net long-term capital gain or loss, and line 16 is typically your net short-term and long-term combined. If those aren't calculated right, it cascades through the rest of your forms.
Quick tip that helped me with a similar 1099-K issue: Get transaction reports from Cash App for the entire year (you can export them) and highlight all transactions that were: 1. Transfers between your own accounts 2. Reimbursements from friends/family 3. Personal items sold at a loss Add notes documenting what each payment was for. Keep this as a PDF with your tax records. This documentation really helps if you get any questions. For the actual tax filing, your approach depends on whether any of this was business activity. If it was all personal (just selling your old stuff), you can often exclude it entirely if you sold items for less than you paid originally.
Do you list every single transaction separately? My Cash App export has like 200+ transactions. Do I seriously need to document each one?
You don't need to list every transaction individually on your tax return, but you should have documentation for them in your records. I grouped similar transactions together - for example, "January-March roommate utility reimbursements: $450" rather than listing each $25-50 payment separately. For your records, I'd recommend at least categorizing each transaction in a spreadsheet. You can summarize these categories on your tax forms, but have the detailed breakdown available if ever questioned. The key is showing you've done your due diligence in separating actual income from money that was just passing through your account.
Does anyone know if these rules are different for higher dollar amounts? I sold my car last year for $18,000 and the buyer used Venmo (I know, probably not smart but it worked out). That single transaction pushed me over the 1099-K threshold and now I'm worried about how to report it.
For a car sale, you need to report it but it's considered a personal capital asset sale, not regular income. You'll use Form 8949 and Schedule D instead of Schedule C. You only pay taxes on the profit (if any) compared to what you originally paid for the car. So if you bought the car for $20,000 and sold it for $18,000, you actually have a $2,000 loss which isn't taxable. If you made a profit, you'd pay capital gains tax on that amount. Just make sure you have documentation of your original purchase price.
Just FYI for next year - I use TaxSlayer for my S Corp and it handles Form 7004 extensions pretty easily. The business version is totally different from their personal tax software though. Make sure you still pay what you estimate you owe though, even with the extension! I learned that lesson the hard way last year with interest and penalties.
Thanks for the tip! How much does the business version cost? And is it user-friendly for someone who's not a tax expert?
TaxSlayer Professional costs around $1,500 for the full package, but they have more limited versions starting around $500 if you only need specific filings like 1120S for S Corps. It's not super user-friendly for beginners honestly - definitely more geared toward professionals. For someone just starting out, I'd probably recommend TaxAct Business instead which is more like $200-300 and more intuitive. You just need to make sure you're getting the business version not the personal one. There's also Drake Tax which many small accounting firms use that's somewhere in the middle price-wise and fairly straightforward.
Something nobody's mentioned - you can file a paper Form 7004 by mail as a last resort! Print the form from the IRS website, fill it out (it's pretty simple), and mail it TODAY with certified mail to prove the postmark date. I had to do this last year when my internet went down on deadline day. As long as it's postmarked by the deadline, you're covered for the extension.
But doesn't paper filing take forever to process? I think I read somewhere that the IRS is still processing paper forms from like a year ago. Would hate to have the extension not show up in their system and then get hit with penalties.
Don't forget to check if your brokerage is correctly applying treaty rates to your dividends. I have investments in Switzerland through Interactive Brokers, and I discovered they were withholding at 35% instead of the treaty rate of 15%. Had to file a special form with the Swiss tax authorities to get the difference refunded. Also, Vanguard has a pretty decent guide to foreign tax considerations for US investors on their website. It's written for their funds, but the principles apply to individual stocks too.
Do you know if there's a time limit for claiming those refunds from foreign tax authorities? I just realized my broker has been withholding at the wrong rate for my German stocks for the past few years.
Most countries have a statute of limitations for tax refund claims. For Germany specifically, you generally have four years from the end of the calendar year in which the tax was withheld to file a claim. So for 2022 withholding, you should be able to file until the end of 2026. For your German stocks, you'll need to file a claim using their specific form (usually Form ZS-DE for US residents) and provide documentation of your tax residence in the US, typically a certificate of residence that you can request from the IRS. Each country has their own process, so you'll need to check the specific requirements for any other countries you have investments in.
Has anyone used H&R Block for reporting foreign investments? My portfolio is about 30% international stocks (mostly through ADRs but some direct foreign shares too) and I'm wondering if their software handles this well or if I should switch to something else.
I used H&R Block last year with a similar portfolio mix. It handled ADRs fine since they come in on a 1099, but for direct foreign investments it wasn't very intuitive. The foreign tax credit section especially was confusing and I wasn't confident I did it right. I switched to TaxAct this year and found their international investment section more user-friendly.
AstroAlpha
Just wanted to add my experience - I had almost the exact same situation with a 1099-R from Vanguard that showed up late. Since it was a direct rollover with nothing taxable (Box 2a empty), my accountant said not to bother with an amendment. She explained that amendments are really only needed if: 1) You owe additional tax 2) Your refund amount would increase 3) You need to correct something substantial For a non-taxable rollover that doesn't change anything, most tax pros don't recommend amending. Just keep the document with your records in case of questions.
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Fatima Al-Farsi
ā¢Thanks for sharing your experience! That makes me feel a lot better. Did your accountant mention anything about the IRS matching program? That's my main worry - getting some scary letter months later saying I "forgot" to report something.
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AstroAlpha
ā¢The IRS matching program mainly focuses on taxable amounts that affect what you owe or are refunded. My accountant explained that when the taxable amount is zero, there's no discrepancy for the matching program to flag, since there's nothing that should have been reported as income. She did recommend keeping the 1099-R with my tax records for at least 3 years just in case any questions came up. But she assured me that in 25+ years of practice, she's never seen the IRS pursue a case where a non-taxable rollover 1099-R wasn't included on a return. Their resources are focused on actual tax discrepancies.
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Yara Khoury
Pro tip: If you use TurboTax, you can actually log back in and check if this would change anything WITHOUT filing an amendment yet. Just sign in, choose to add another 1099-R, enter the information, and see if it changes your refund amount or tax due. If nothing changes, you can just cancel without submitting. I did this last year with a late-arriving 1099-INT and confirmed it wouldn't change my refund at all. Saved me the hassle of an amendment.
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Keisha Taylor
ā¢This is super smart! Just make sure you don't accidentally submit it as an amendment. I've done this "test" with TurboTax before to check if certain deductions would make a difference. Just be careful to exit without saving/submitting.
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