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Has anyone actually tried exercising and selling in the same tax year to avoid AMT entirely? My financial advisor suggested this approach, but I'm not sure if it works in all situations.
That strategy can work but you lose the potential for LTCG treatment. If you exercise and sell in the same year, the entire gain is treated as ordinary income. So you avoid AMT but potentially pay more in regular tax. It really depends on how much the stock has appreciated and what your regular income is. For my situation with a startup that had 5x growth, it was actually better to take the AMT hit and then get LTCG treatment a year later, even considering the time value of money. Run the numbers both ways!
One thing that really helped me understand this was realizing that AMT creates a "parallel tax system" where you essentially maintain two sets of books. When you exercised your ISOs, you paid AMT on the bargain element, but that payment creates an AMT credit that you can use in future years when your regular tax exceeds your AMT. The key insight is that when you sell after holding for over a year, your AMT basis in the stock is higher than your regular tax basis (because it includes that bargain element you already paid AMT on). This means your AMT gain will be smaller than your regular tax gain, creating what's called a "negative AMT adjustment" that helps you recover the AMT credit. So you're not being taxed twice - you're actually on track to recover some of that AMT you paid through the credit system. Just make sure you file Form 8801 to claim your AMT credit when you sell!
This is such a helpful explanation! I'm new to dealing with stock options and the "parallel tax system" concept really clicked for me. Quick question - do I need to do anything special to track my AMT basis, or does the tax software usually handle that automatically? I want to make sure I don't mess up the Form 8801 when I eventually sell my shares.
As a newcomer to this community, I want to thank everyone for this incredibly detailed discussion! I'm dealing with my first Schedule AI this year after starting a side business alongside my W-2 job, and I was completely overwhelmed by the form. The explanations here about how each period creates its own "snapshot" projection have been game-changing for my understanding. I was making the same mistake as the original poster - thinking I needed to somehow predict my entire year's business income back in January and divide it into equal quarterly payments. What really clicked for me was understanding that the annualized income method is actually protecting taxpayers with variable income. My business had slow revenue in Q1-Q2 but picked up significantly in Q3-Q4. Without Schedule AI, I would have been penalized for not paying 25% of my actual annual tax by March 15th, even though my business barely existed then! The fact that you ended up only $20 off your total tax liability really shows how well the system works when properly applied. It gives me confidence that I can navigate my own Schedule AI calculations correctly. This thread has been more educational than hours of trying to decipher IRS publications - thank you all for sharing your experiences and insights!
Welcome to the community! Your side business situation is exactly why Schedule AI exists - it's so common for new businesses to have that slow start followed by growth later in the year. I went through something similar when I started freelancing, and the form initially seemed designed to trip me up rather than help. What really helped me was keeping detailed records of my business income by quarter, which made filling out Schedule AI much easier. Since your business picked up in Q3-Q4, you probably found that your required Q4 payment was higher than earlier quarters, but that's exactly how it should work - you're paying based on your actual income pattern, not some artificial projection. The $20 accuracy that the original poster achieved really is impressive and shows the system working as intended. I'd be curious to hear how close your calculations ended up being! Most of us were off by much more in our first year with variable income.
As a newcomer to this community, I'm amazed by how helpful this discussion has been! I've been struggling with Schedule AI myself after having irregular income this year - started with steady W-2 employment, then had a period of unemployment, followed by some freelance work that came in chunks. Reading through everyone's explanations, especially the "snapshot" and "time machine" analogies, finally made the annualized income method click for me. I was making the classic mistake of thinking I should have predicted my entire year's income pattern back in January and made proportional payments. What really resonates is how this method actually protects taxpayers rather than penalizes them. My freelance income was heavily weighted toward the end of the year, and without Schedule AI, I would have been expected to pay estimated taxes on income I hadn't even earned yet. The original poster's situation with the November Roth conversion is such a perfect example - you can't be expected to predict and pay for a financial decision you hadn't made yet! The fact that they ended up only $20 off shows the system really does work when you understand it properly. Thank you all for taking the time to explain this so clearly. This thread has been more valuable than any official IRS guidance I've tried to read!
Has anyone used TurboTax to amend their return when they had these weird codes? I'm in a similar situation with code 290 and need to submit an amendment but worried it'll mess things up more.
I used TurboTax to amend my 2021 return when I had similar code issues. Just make sure you wait until your original return is fully processed (you'll see a 150 code on your transcript) before filing the amendment. If you amend too early like the original poster did, it can cause even more delays because the systems don't know how to handle overlapping processing.
I went through almost the exact same situation last year! The 290 code combined with your audit being reversed is actually really good news. Here's what likely happened: When you filed your amended return right around the time of the audit, it created a processing conflict in the IRS system. The 290 code you're seeing is the IRS making an adjustment to reconcile your original return with the audit findings (which were then reversed) and your amendment. The fact that you now see code 846 (as you mentioned in your follow-up) means your refund has been approved and is being issued. That date is when the Treasury will send the payment - usually takes 1-3 business days to hit your bank account if you have direct deposit set up. For your stimulus payments, definitely claim the Recovery Rebate Credit on your 2022 return. Since your 2021 return was tied up in processing, you likely didn't receive the payments that were based on that return. The IRS will cross-reference what you've already received and give you credit for any missing amounts. One tip: keep checking your transcript weekly because sometimes additional codes appear that give you more details about processing timelines. After dealing with this mess for over a year, seeing that 846 code must feel amazing!
This is incredibly helpful! I'm dealing with a similar transcript maze right now and seeing code 290 with no clear explanation of what it means. The timing conflict between amended returns and audits makes total sense - I bet that's exactly what happened to create this whole mess. Quick question though - when you say to keep checking the transcript weekly, is there a specific day of the week when the IRS typically updates these codes? I've been checking randomly and wondering if there's a pattern to when new information appears. Also, for the Recovery Rebate Credit, do you remember if there were any income limits or other restrictions? I'm worried I might not qualify even though I never received the payments originally.
Quick question - I mailed in my 2022 return last month but haven't heard anything back yet. Is there a way to check if the IRS received it? I didn't e-file because I thought you couldn't do that for prior year returns.
You can check the status of any return by creating an account on the IRS website: https://www.irs.gov/payments/your-online-account It lets you see if they've received and processed your return. But be patient - paper returns take 6-8 weeks to process during normal times, and way longer during busy season or if there's a backlog. I mailed mine in January and it took until March to show up in their system. Also, many tax software companies actually DO allow e-filing for 2022 returns even now. Much faster than paper filing!
Don't beat yourself up about being late - life happens and you're definitely not the first person to miss a filing deadline during a tough time! The good news is you're still well within that 3-year window to claim your refund. One thing I'd add to the great advice already given: make sure you have all your 2022 documents before you start. You'll need your W-2s, any 1099s, receipts for those medical expenses and charitable donations you mentioned, etc. If you're missing any tax documents from employers or financial institutions, you can request copies or sometimes find them in your online accounts from that year. Also, since you mentioned medical expenses - remember that for 2022, you could only deduct medical expenses that exceeded 7.5% of your adjusted gross income. It's worth calculating whether itemizing will actually give you a bigger deduction than the standard deduction was for 2022 ($12,950 for single filers). You've got this! Getting your finances back on track is a great step forward.
This is really helpful advice! I'm actually in a similar situation and was wondering about the medical expense threshold. Just to clarify - if my AGI for 2022 was around $45,000, I'd need more than $3,375 in medical expenses (7.5% of $45k) before any of it becomes deductible, right? I had about $2,800 in medical bills that year, so it sounds like I'd be better off taking the standard deduction instead of itemizing?
Amaya Watson
17 Has anyone actually had the IRS contact them over a wrong address on a W2? I've had this happen twice (once my employer put the wrong apt number, once they used my old address) and filed with my correct address both times. Never heard a peep from the IRS about it.
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Amaya Watson
ā¢2 I've never heard of anyone having issues with this either. The IRS deals with millions of returns - they're not going to flag something as minor as a house number being wrong when all the important financial info matches up.
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Natasha Kuznetsova
I'm a tax preparer and can confirm what others have said - address discrepancies on W-2s are extremely common and won't cause any issues with your tax filing. The IRS uses your SSN as the primary identifier, and the financial data (wages, withholdings) is what matters for processing your return. When you file your 2024 tax return, just use your correct current address. This automatically updates your address of record with the IRS. I've prepared thousands of returns over the years with similar situations and have never seen the IRS flag or delay a return due to a W-2 address mismatch. Your concern about missing correspondence is understandable, but since you'll be filing with your correct address, any future IRS communications will go to the right place. The only time address issues become problematic is if there are discrepancies in the actual tax data (income amounts, withholdings, etc.), which isn't your situation.
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James Johnson
ā¢Thank you for the professional perspective! It's really reassuring to hear from someone who deals with this regularly. Just to clarify - when you say "automatically updates your address of record," does this happen immediately when the return is filed, or only after it's processed? I'm wondering if there's any timing issue where the IRS might try to send something to the old W-2 address before my return gets fully processed.
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