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Has anyone tried doing this calculation on TurboTax? I've got a similar situation with about $8K in carried over losses from last year and $11K in gains this year, but TurboTax seems to be applying my losses weirdly. It's only using part of my carryover.
I used TurboTax for this exact situation last year. Make sure you're entering your capital loss carryover from last year correctly - there should be a specific section for entering carryover amounts. If you just enter it as a current year loss, it will process it incorrectly. Also double-check that you properly categorized your carryover as short-term or long-term (or properly split between both if applicable). TurboTax worked fine for me once I entered everything in the right place.
This is a great question that trips up a lot of people! The key thing to understand is that the $3,000 annual limit only applies when you're using capital losses against ordinary income (like your salary). When you have actual capital gains, you can use your entire capital loss carryover to offset those gains without any annual limit. In your specific case with $13.5K loss carryover and $16K gains, you would indeed subtract the full $13.5K from your $16K gains, leaving you with only $2.5K in net capital gains to be taxed on this year. No remaining loss would carry forward to Y3 since you've used it all up. The IRS designed it this way because capital losses and gains are considered "like-kind" - losses from selling investments should be able to fully offset gains from selling investments. The $3K limit is really just a consolation prize when you don't have any gains to offset against. Make sure you're correctly categorizing your carryover losses as short-term vs long-term though, as the netting rules do matter for determining your final tax rate on any remaining gains.
Just want to point out that if you do decide to withdraw from your 401k, remember that the plan administrator will usually withhold 20% for federal taxes, which might not be enough depending on your tax bracket. So you'd need to withdraw more than just the amount you owe the IRS to account for the taxes on the withdrawal itself.
I was in a very similar situation last year and ended up going with the estimated payment route rather than touching my 401k. Here's what I learned: even though you're over 59.5 and won't face the early withdrawal penalty, the tax implications can be tricky. The biggest issue is that you'll need to withdraw MORE than the $5,400 you owe because the withdrawal itself becomes taxable income. Plus, depending on your current tax bracket, that additional income could push you into a higher bracket for the year. I'd strongly recommend calculating both scenarios before deciding. For the estimated payment, you can still make the Q4 payment by January 15th through the IRS website - it's actually pretty straightforward once you set up an account. And if your income was uneven this year (sounds like it might have been), look into Form 2210 and the annualized income method - it could save you from underpayment penalties on earlier quarters. The peace of mind from keeping your retirement savings intact and growing was worth it for me, even with a small penalty.
Has anyone used TurboTax for reporting with HIFO? I've got about 50 transactions across Coinbase and Kraken, and I'm wondering if it's worth paying for their premium version or if I should use something else entirely.
Another important consideration with HIFO is that it can create some unexpected complications if you're planning to hold crypto long-term. Since you're always selling your highest-cost basis coins first, you might inadvertently be selling newer purchases that haven't reached the one-year holding period for long-term capital gains treatment. This means you could end up with more short-term gains (taxed as ordinary income) instead of long-term gains (lower tax rates). Also, if you ever need to demonstrate a clear investment strategy to the IRS, constantly cherry-picking the highest cost basis assets might look like you're purely focused on tax avoidance rather than following a consistent investment approach. The IRS prefers methods that reflect actual investment decisions rather than purely tax-motivated choices. For your 50 transactions, make sure whatever software you use can generate the detailed Form 8949 that shows each specific transaction with dates and cost basis - the IRS will want to see this level of detail if they ever audit your crypto reporting.
I went through this exact same nightmare situation two years ago! The confusion between what you select during EIN application vs. actual S-Corp election is SO common. Here's what I learned: Just checking "S-Corp" on your EIN application does NOT automatically elect S-Corp status. You need to file Form 2553 separately within 75 days of formation (or by March 15th of the following year) to actually make the election stick. In my case, I thought I had elected S-Corp status but never filed the 2553. I was technically still a disregarded entity the whole time, which meant no back filing requirements for my dormant LLC. The easiest way to know for sure is to call the IRS at 800-829-4933 with your EIN and ask them directly what elections they have on file. If they don't show an S-Corp election, you're likely still a disregarded entity and don't need to worry about those 1120-S filings or penalties. Don't panic until you confirm your actual status - you might be stressing over nothing!
This is exactly the clarity I needed! I've been losing sleep over this for weeks thinking I was racking up thousands in penalties. The distinction between checking a box during EIN application vs. actually filing Form 2553 makes so much sense now. I'm pretty sure I never filed the 2553 form because I would have remembered that paperwork. Going to call the IRS number you provided first thing Monday morning to confirm my status. Thank you for breaking this down so clearly - wish I had found this information sooner!
Just wanted to add another data point to this discussion - I was in a very similar situation last year with my single-member LLC. Like many others have mentioned, the key distinction is between selecting "S-Corp" during your EIN application versus actually filing Form 2553 to make the election official. In my case, I had checked the S-Corp box when applying for my EIN but completely forgot about the separate Form 2553 requirement. I spent months worrying about potential penalties until I finally called the IRS Business line. Turns out I was still classified as a disregarded entity since no Form 2553 was ever filed. One thing I'd add to the great advice already given - if you do discover you properly elected S-Corp status and need to file back returns, consider working with a tax professional who specializes in S-Corp compliance. The penalty abatement process can be tricky to navigate on your own, especially when you're dealing with multiple years of missed filings. Also, for future reference, if you ever do want to make an S-Corp election, set a calendar reminder for the Form 2553 deadline - it's easy to miss that 75-day window after formation.
Yuki Yamamoto
I've been dealing with amended returns for years and here's my tried-and-true approach: Call 1-800-829-1040 on Tuesday or Wednesday right at 7:00 AM ET sharp. Have your SSN, both returns (original and amended), and your bank routing info ready. But here's the insider tip most people don't know - ask the rep to check for any "unpostables" on your account. Sometimes amended returns get stuck because of small mismatches (like a slightly different name format from what's in their system). The rep can usually resolve these on the spot. Also, if you're expecting a refund over $1,000, they might transfer you to a different department that handles larger refunds - this is normal, don't hang up! The wait time resets but you'll get someone who can actually move things along. I've seen people get their refunds released same-day after being stuck for months once the right person looked at their case.
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Samuel Robinson
ā¢This is incredibly helpful! I had no idea about asking for "unpostables" - that sounds like it could be exactly what's happening with mine. Quick question: when you mention the name format mismatch, do you mean like if I used my full middle name on the amended return but just a middle initial on the original? I'm wondering if that could be why mine is stuck since I think I might have done exactly that. Also, is there a specific way to ask about the unpostables, or do the reps know what you mean when you use that term?
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Esteban Tate
Based on everyone's experiences here, I'd suggest trying multiple approaches since amended returns can be tricky. First, try calling 1-800-829-1040 early Tuesday morning around 7 AM ET with all your documentation ready (SSN, both returns, AGI from both, mailing address). If that doesn't work, the Taxpayer Advocate Service at 877-777-4778 might have shorter wait times. Since you filed in January and it's now March with no updates in the WMAR tool, you're getting close to that 16-20 week processing window others mentioned. One thing to consider - if this is causing financial hardship, definitely mention that when you call as it can sometimes expedite processing. Also worth checking your online IRS account for any transcript updates that might show processing codes before spending hours on hold. Sometimes the system updates there before the WMAR tool catches up. Good luck getting through - the waiting game with amended returns is frustrating but you're definitely entitled to know what's happening!
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Dmitry Volkov
ā¢Thanks for the comprehensive summary! I'm in a similar boat - filed my 1040X in January and still nothing showing up in WMAR. The financial hardship angle is interesting since I was counting on this refund for some unexpected medical bills. Do you know if there's a specific threshold they use to determine "financial hardship" or is it more subjective based on what you tell them? Also, when you mention checking the online IRS account for transcript updates, should I be looking for the "Account Transcript" or "Record of Account Transcript" for the year I amended? I've been checking periodically but wasn't sure which one would show the processing codes first.
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