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Mila Walker
I'm a bit late to this thread but just wanted to add that you should definitely keep detailed records of all your crypto transactions - purchase dates, sale dates, prices, fees, etc. The burden of proof is on you if questioned. I believe Binance only issues 1099-Bs for customers with transactions exceeding $20,000 or 200 transactions in a year. For smaller accounts, they often don't issue any tax forms at all, which is why you might not see anything on your transcript.
Logan Scott
ā¢I've heard people recommend using crypto tax software that keeps track of your cost basis across different platforms. Do you think that's necessary, or is just keeping my own records in a spreadsheet good enough?
Mila Walker
ā¢A spreadsheet can be sufficient if you're diligent and have relatively simple crypto activity. I started with spreadsheets myself. But they become cumbersome quickly, especially if you're dealing with multiple exchanges, token swaps, staking rewards, or DeFi transactions. The key advantage of specialized crypto tax software is that it handles complex situations like FIFO vs LIFO accounting methods, tracks cost basis across platforms, and automatically identifies which specific coins were sold from your holdings. The IRS allows different accounting methods, and your choice can significantly impact your tax liability, especially if you bought the same crypto at different price points.
Chloe Green
Anyone tried FreeTaxUSA for reporting crypto? I've used them for years but never had to report crypto until now.
Lucas Adams
ā¢I used FreeTaxUSA for my crypto last year. They handle it pretty well! You'll need to enter each transaction manually on Form 8949, but the interface makes it straightforward. Just make sure you've calculated your cost basis correctly beforehand. If you have tons of transactions, it can get tedious, but for a reasonable number it works great.
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Freya Larsen
Anybody know why there's such a big gap between when they "process" your return and when they actually send the money? Seems like once they approve it they could just send the refund immediately. Mine was processed on 2/9 but refund date shows 2/21...that's ridiculous.
They do this on purpose to earn interest on holding your money. My brother works for Treasury (not IRS) and says it's all about float time on billions of dollars.
Omar Zaki
Pro tip: If you have the 846 code on your transcript with a specific date, that's your ACTUAL refund date. That's the date they send the payment to your bank. Then it usually takes 1-2 business days for your bank to post it. But the IRS doesn't always hit that exact date - sometimes it comes a day or two early. The processing date is different from the refund issued date.
Chloe Taylor
ā¢I see a code 570 on mine. What does that mean? My tax guy says everything is fine but it's been 5 weeks...
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Ava Garcia
If you're in a real hurry and can't wait for transcripts, you might be able to use your final paystubs from those years. They usually have year-to-date totals that would match or be close to your W2 amounts. Not ideal, but in a pinch it works. When I filed late for 2019, I used my December paystub and the IRS didn't question it. Just make sure you note on your return that you're using reconstructed information based on paystubs since the employer isn't responding.
Miguel Silva
ā¢Is this actually legal though? I thought you had to use the exact W2 information or get official transcripts from the IRS.
Ava Garcia
ā¢It's absolutely legal to file with your best available information. The IRS would much rather have you file with reconstructed information than not file at all. You should make a good faith effort to get the correct documents first, but if that's not possible, you have to work with what you have. Just be sure to note on your return that you're using estimated information based on available records. The IRS can always correct it later if there are significant discrepancies, but at least you've fulfilled your filing obligation and stopped the failure-to-file penalties from growing.
One thing nobody mentioned - if you're due a refund for those years, you only have 3 years from the original due date to claim it. So for 2021, you have until April 2025 (since it was due April 2022). After that, you can still file but kiss any potential refund goodbye. If you owe money though, there's no time limit for the IRS to collect, and penalties and interest keep building. So definitely prioritize filing those past returns ASAP.
Are you sure about this? I thought the 3-year limit was from when you actually file, not the original due date. Is this different for different tax situations?
I'm 100% certain it's 3 years from the original due date, not from when you file. This is a common misconception. This is straight from the IRS: you must file your claim for a credit or refund within 3 years from the date you filed your original return or within 2 years from the date you paid the tax, whichever is later. So for a 2021 tax return that was due in April 2022, you have until April 2025 to claim any refund. After that, even if you were owed money, it becomes the property of the U.S. Treasury. The IRS is strict about this timeline and doesn't make exceptions. That's why filing sooner rather than later is so important, especially if you think you might be owed money!
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Don't forget to consider state tax implications of the switch! Depending on your state, there can be significant differences in how S Corps vs C Corps are taxed at the state level. For example, in California, S Corps pay a 1.5% tax on net income (minimum $800), which is different from the C Corp rate. Some states don't recognize S Corps at all for state tax purposes!
Miguel Ortiz
ā¢This is such an important point. I'm in New York and was surprised to learn they have an additional tax for S corporations that I wasn't expecting. Always research your specific state requirements before making the switch.
The timing of when you make the conversion matters a lot. If your business has significant assets that have appreciated in value (like real estate, equipment, intellectual property), converting can trigger a tax on that appreciation. If your business is mainly service-based with minimal assets, this is less of a concern. But if you do have valuable assets, consider getting them properly valued before making any decisions.
Oliver Becker
Don't forget about the AMT implications with ISOs! Even if you have a disqualifying disposition, you might still need to figure out if you paid any AMT in the year you exercised. If you did, you might be eligible for an AMT credit. The whole ISO system is ridiculously complicated. When I exercised some ISOs in 2022, I had to pay AMT that year. Then when I sold in 2023 (disqualifying disposition), I got ordinary income but was also eligible for an AMT credit. Make sure you're tracking all this stuff.
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Miguel Alvarez
ā¢I'm honestly not even sure if I paid AMT when I exercised these. How would I know? Would it have been obvious on my 2023 return or is this something that could have happened without me realizing it?
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Oliver Becker
ā¢Check your 2023 tax return for Form 6251 (Alternative Minimum Tax). If you paid AMT, it would show up there and on line 1 of Schedule 2 of your Form 1040. If you did pay AMT in 2023 when you exercised, you'll likely be eligible for an AMT credit on your 2025 return (for the 2024 tax year when you sold). You'll need to file Form 8801 (Credit for Prior Year Minimum Tax) along with your return. This credit can potentially offset some of the tax impact from your disqualifying disposition.
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Natasha Petrova
Something else to consider with ISOs - if your company is private or was private when you exercised, the calculation of the bargain element can get really messy. Companies use 409A valuations which might not match what you think the shares are worth. My company went public 8 months after I exercised some ISOs and the 409A value at exercise ($12/share) was WAY lower than the IPO price ($47/share). I made a disqualifying disposition but the bargain element was calculated based on the lower 409A value, not the public market value when I sold.
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Javier Hernandez
ā¢Yep, this happened at my last job too. But be careful - some companies mess up the reporting on disqualifying dispositions. My employer reported the wrong amount on my W-2 (they used the sale price instead of FMV at exercise for calculating the ordinary income). Had to get an amended W-2 which was a huge hassle. Double-check your W-2 when you get it!
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