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Omar Hassan
As someone who prepares taxes professionally, I can tell you that what your family member did isn't technically correct, but it's also not unusual. Many preparers will summarize Form 8949 transactions, especially when there are dozens or hundreds of trades. However, there are right and wrong ways to do this. The right way: 1. Separate short-term and long-term transactions 2. Use the proper checkboxes (A, B, C for short-term; D, E, F for long-term) 3. Use proper adjustment codes if needed The fact that long-term transactions were included in the short-term section is definitely an error that should be corrected.
What about the reporting to the IRS? If the transactions are summarized, does the IRS get the detailed listing some other way? I always thought they match each individual transaction?
Omar Hassan
ā¢The IRS generally only receives what's actually reported on your tax return. If the transactions are summarized, they don't automatically get a detailed breakdown elsewhere. However, brokerages do report the detailed transactions to the IRS on Form 1099-B. The IRS's matching program typically works at a summary level first - they compare the total proceeds reported by your brokerages against what's on your return. If there are significant discrepancies, that might trigger further review where they would request the detailed information. That's why it's essential to at least have the summary amounts match what the brokerages reported, even if you're summarizing.
Diego Chavez
Has anyone used the option to attach a statement instead of filling out all the 8949 lines? My tax software mentioned I could do this but wasn't sure if it would cause issues.
NeonNebula
ā¢I did that one year when I had over 500 transactions. You can attach a separate statement that has all the required 8949 information in a similar format. The key is making sure that the statement has all the same column headers and information that would be on the actual form. Then on the 8949 itself, you enter "See attached statement" with the totals on a single line.
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Pedro Sawyer
Just to add some clarity on the 1042-S issue specifically - I'm a university administrative assistant who deals with these for international students all the time. When a 1042-S is reissued, the issuer (usually the university or employer) is required to: 1. Check the "corrected" box at the top of the 1042-S 2. Submit the corrected form electronically to the IRS 3. Provide you with a paper copy marked "corrected" The most common problem I see is that sometimes the issuer provides the corrected copy to the recipient but forgets to submit the electronic correction to the IRS. Or they submit it late, after the IRS has already started their matching program. Ask your issuer to confirm they submitted the electronic correction AND the date they submitted it. If they submitted it after you filed your tax return, that's likely the source of the problem.
Rosie Harper
ā¢Thank you so much for this specific information! I just checked my 1042-S again and it DOES have the "corrected" box checked at the top. I hadn't even noticed that before. So I'm guessing you're right that the timing between their correction and my filing might be the issue. I'll contact the issuer tomorrow and specifically ask about when they submitted the electronic correction to the IRS. That seems like the most likely explanation for why the IRS thinks there's a mismatch when my numbers actually match what's on my form.
Pedro Sawyer
ā¢Glad I could help! That "corrected" box is definitely your smoking gun. Based on what you've said, I'm almost certain the timing is the issue. When you contact the issuer, ask them to provide you with documentation showing both the original and corrected submission dates. Having this documentation will make resolving the issue with the IRS much easier. You can include it with your response to show exactly what happened and why there appears to be a mismatch in their system.
Mae Bennett
Has anyone actually resolved a 1042-S issue through the IRS website or is calling really the only way? I'm having a similar issue but really don't want to spend hours on the phone if I can avoid it.
In my experience, these specific matching issues almost always require a phone call or a written response. The online account tools don't have functionality to resolve document matching problems. Your best option is probably to prepare a written response with copies of your documents and mail it to the address on your notice.
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Taylor To
One thing to keep in mind is that there are different safe harbor requirements depending on your income level. If your AGI was over $150,000 last year, you need to cover 110% of last year's tax liability (instead of 100%) to meet the safe harbor. Also, don't forget that if you're self-employed, you still need to make sure you're covering your self-employment taxes through either estimated payments or additional withholding. Those can add up fast!
Ella Cofer
ā¢Do you know if the safe harbor is calculated on total tax liability or just income tax? Like does it include the self-employment tax portion too when figuring the 100% or 110% of last year's taxes?
Taylor To
ā¢The safe harbor amount is based on your total tax liability, which includes both income tax and self-employment tax. So when people talk about covering 100% (or 110% for higher incomes) of last year's tax, they're referring to the total amount on line 24 of your Form 1040 from last year - that's your total tax, including self-employment taxes. That's why self-employment income can really complicate things, because you're responsible for both the employee and employer portions of Social Security and Medicare taxes, which adds about 15.3% on top of your regular income tax.
Kevin Bell
Just wanted to add that you can also adjust withholding from other sources besides your W-2 job if that's easier. My spouse adjusts withholding from their pension for this exact reason whenever we have unexpected 1099 income. Form W-4P is used for pension withholding, and Form W-4V for certain government payments like Social Security. All of these count as withholding that's treated as paid evenly throughout the year!
That's a great tip! I didn't realize you could adjust Social Security withholding too. Is there a limit to how much you can withhold from Social Security benefits specifically?
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There's actually a built-in report for capital gains in H&R Block that many people miss. Go to Reports > Tax Reports > Capital Gains and it will generate a summary you can print to PDF and then copy from there. Not as convenient as direct Excel export but better than nothing!
Where exactly is this in the 2025 version? I'm looking under Reports but don't see Tax Reports as an option. Is it only available after you complete Schedule D or something?
In the 2025 version they moved it slightly. Look under Reports > My Documents > Generated Reports and then you need to click "Create New Report" and select Capital Gains from the dropdown list. It's definitely not intuitive! The report won't be available until you've entered at least some Schedule D information. Once generated, it creates a nice PDF that you can open in Adobe Reader and copy text from. The data comes out pretty clean and just needs a little formatting in Excel.
If nothing else works, I ended up using a free screen recording tool (OBS Studio) to scroll through all my entries slowly, then typed them up while watching the recording. Not elegant but worked for me when I had a similar problem with 43 trades last year.
Dylan Cooper
ā¢That sounds incredibly tedious! How long did it take you to manually enter all 43 trades?
Zachary Hughes
Just a heads up - don't forget that even though your fiancee might not owe federal income tax because the prize value is below the standard deduction, she could still be on the hook for self-employment tax if this is considered self-employment income (like if she's a Mary Kay consultant herself). Self-employment tax kicks in once you make $400 or more in self-employment income, which is way lower than the standard deduction threshold. That includes the 15.3% for Social Security and Medicare that normally gets withheld from a W-2 job's paycheck.
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Mia Alvarez
ā¢Does winning a trip as a customer count as self-employment though? I thought self-employment was only if you're actually selling stuff or providing services. The post says she won it through her consultant, which makes it sound like she's just a customer who entered some kind of contest?
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Zachary Hughes
ā¢You're right about the distinction. If she's just a customer who won a prize, then it would be reported as "Other Income" on Schedule 1, not subject to self-employment tax. The key is how the 1099-MISC is filled out - Box 3 is for "Other Income" like prizes and awards, while Box 1 would be for self-employment income. The OP should check which box on the 1099-MISC has the amount listed. If it's in Box 3, then it's just regular income (not subject to self-employment tax). If it's in Box 1, then Mary Kay might be incorrectly classifying it as self-employment income.
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Carter Holmes
Did you guys enter this trip as a prize when filing, or as a gift? Because I think gifts aren't taxable to the recipient (the giver pays any gift tax). Maybe there's a way to argue this was a gift from the Mary Kay consultant rather than a prize?
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Matthew Sanchez
ā¢That's unfortunately not going to work. The IRS has very clear rules distinguishing gifts from prizes. A gift must be given out of "detached and disinterested generosity" with no expectation of benefit to the giver. When a company like Mary Kay gives a trip through a promotion or contest, it's clearly for business purposes (advertising, client retention, etc.), so it's a prize, not a gift. The 1099-MISC confirms this classification. Trying to reclassify it as a gift would likely raise red flags with the IRS.
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