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Tax filing extension pros & cons - better to file superseding return or amendment?

I'm trying to decide whether to file for a tax extension this year, and I'm curious about potential advantages. I know that if I get an extension, I could file a superseding return instead of an amended return if needed. What exactly is the benefit of that approach? My tax situation is pretty complex this year. I have some W-2 income but I'm mainly working as a consultant with 1099s. I have a single-member LLC that's taxed as a pass-through on my Schedule C. When I started my business in 2021, I elected to use the accrual method since I was in a lower tax bracket but anticipated growth, so I wanted to shift more income into that first year rather than pushing it to 2022. Last year I also started investing more seriously. I opened a brokerage account after maxing out my tax-advantaged accounts. Made some risky trades that actually worked out pretty well, including getting lucky with the whole meme stock craze in January. I've since decided to move toward more traditional investments, but I now realize I wasn't thinking about the tax implications of trading futures, commodities, REITs, partnerships, etc. I'm expecting several K-1s to arrive, but I'm not sure how many or when they'll show up. I'm also considering hiring a CPA to help me switch from accrual to cash basis accounting so my 1099s will better align with my actual earnings. My current plan: 1. File for extension before April 15 2. File my taxes on April 15 anyway and pay what I owe 3. Pay Q1 estimated taxes using safe harbor (110% of previous year's tax * 0.25) 4. If late K-1s arrive or I change accounting methods, file a superseding return and adjust my quarterly payments accordingly Would I still face underpayment penalties and interest either way? Is there any real advantage to filing a superseding return versus an amendment? Or should I just file for extension, pay an estimated amount on April 15, and wait until October to file the actual return?

Natalie Adams

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Have you considered just paying a CPA to handle this for you? With the complexity you're describing (especially with the accounting method change), it might be worth the money. My tax situation got similarly complicated last year and I bit the bullet and hired someone. Cost me about $800 but saved me thousands in deductions I would have missed and countless hours of stress.

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Olivia Harris

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I've been considering it, but I'm worried about finding someone who really understands both the 1099 contractor side AND the investing complexities. Did you find someone who specialized in both areas? How did you go about finding them?

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Natalie Adams

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I found my CPA through a referral from another consultant who also dabbles in investing. That's probably your best bet - ask other contractors who also invest who they use. Most experienced CPAs can handle both business and investment income, but you definitely want someone who regularly works with self-employed people and investors rather than someone who mainly does simple W-2 returns. When interviewing potential CPAs, ask specifically about their experience with accounting method changes and investment income from partnerships/REITs. A good CPA will be able to immediately discuss the implications of these situations without hesitation.

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One thing nobody's mentioned yet - if you file for an extension and pay what you think you'll owe, you'll avoid the late filing penalty (which is much higher than the late payment penalty). The late filing penalty is 5% of unpaid taxes for each month your return is late, while the late payment penalty is just 0.5% per month.

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Amara Torres

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But don't you still have to pay by April 15 regardless of whether you file an extension? So if you underestimate what you owe, you'll still get hit with penalties, right?

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Yara Sayegh

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Yes, you still need to pay by April 15 even with an extension. The extension only gives you more time to file your return, not to pay what you owe. If you underestimate and don't pay at least 90% of your actual tax liability (or meet the safe harbor rule of paying 100%/110% of last year's tax), you'll face underpayment penalties. However, the key benefit is avoiding the much steeper late filing penalty if you can't get your return completed by the deadline. It's basically damage control - you might still owe some interest and underpayment penalties, but you avoid the worst penalty (late filing) by getting that extension filed on time.

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This exact situation is why I only use licensed daycare centers now even though they're more expensive. They're legitimate businesses with tax IDs, proper contracts, and regular receipts. Worth every penny for the peace of mind during tax season and for knowing they meet safety standards. For your current situation, I'd try one more written request (certified mail) for her information, explicitly stating what you paid her for the year. If she still refuses, proceed with filing with the documentation you have and start looking for new care.

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I went through something very similar with my nanny last year. She was paid $400/week for 10 months and when tax time came, she completely ghosted me about providing her SSN. I was panicking about losing out on a significant tax credit. Here's what I learned from my tax attorney: You absolutely can still claim the Child and Dependent Care Credit even without the provider's SSN. The key is documenting that you made a reasonable effort to obtain it. Send her a formal written request via certified mail asking for her tax information using IRS Form W-10. Keep the receipt and any responses (or lack thereof). On Form 2441, there's a checkbox specifically for situations where you requested but couldn't obtain the provider's taxpayer identification number. Check that box and attach a brief explanation of your attempts to get the information. Your Venmo records are excellent documentation. For the cash payments, create a simple log showing dates and amounts that align with your agreed-upon weekly rate. The IRS understands that some childcare payments are made in cash. One thing to consider: if she's being paid $385/week by you and likely similar amounts by other families, she could owe substantial back taxes. The IRS has ways of cross-referencing childcare providers when multiple families claim the same person. You're not responsible for her tax compliance - focus on claiming what you're legally entitled to. I'd also start quietly looking for backup childcare options now, just in case this relationship becomes untenable after tax season.

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This is really helpful advice, thank you! I'm curious about the tax attorney consultation - was that expensive? I'm trying to figure out if it's worth the cost versus just proceeding with what I've learned here. Also, when you say the IRS has ways of cross-referencing providers, does that mean they automatically investigate everyone who gets claimed by multiple families? I don't want to cause problems for her unnecessarily, but I also can't afford to lose this tax credit. Did your nanny ever find out that you filed without her SSN, and if so, how did she react?

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This is a really troubling situation, and I'm glad you caught it early. The fact that the VIN on the IRS letter doesn't match your vehicle is a major red flag that suggests either a serious clerical error or potentially fraudulent activity by the dealership. Here's what I'd recommend doing immediately: 1. **Document everything** - Take photos of your vehicle's VIN (usually visible through the windshield on the driver's side), gather all your purchase paperwork, and keep that IRS letter safe. 2. **Contact the IRS directly** - Don't wait on this. Call the Clean Vehicle Credit hotline at 1-866-455-7438. Explain the VIN mismatch and that you never knowingly transferred your credit. 3. **File complaints** - Report this to your state's Attorney General, the Better Business Bureau, and your state's motor vehicle dealer licensing board. If there's fraud involved, they need to know. 4. **Check your credit report** - Make sure no other vehicles or loans have been opened in your name. The good news is that the VIN mismatch actually works in your favor - it's clear evidence that something went wrong in the process. This isn't just a case of buried paperwork; there's a legitimate administrative error or worse happening here. Keep pushing for answers and don't let the dealership's non-responsiveness discourage you. You have rights as a consumer, and this situation definitely warrants investigation.

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Aisha Mahmood

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This is excellent advice! I'd also suggest reaching out to your local news stations if you don't get anywhere with the official channels. Consumer protection segments love stories like this, especially when there's potential dealer fraud involved. The threat of bad publicity often gets dealerships to respond much faster than official complaints. Also, consider checking if your state has a specific automotive ombudsman program - many states have these to help resolve disputes between consumers and dealers. They often have more leverage than general consumer protection offices. The VIN mismatch really is the smoking gun here. There's no innocent explanation for why a completely different vehicle's information would be on your IRS notice unless someone made a very serious error or is doing something shady with multiple customers' credits.

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This situation definitely needs immediate attention, especially with that VIN mismatch. I work in automotive compliance and have seen similar cases where dealers submitted incorrect paperwork to the IRS, sometimes accidentally but occasionally as part of larger schemes. The fact that you have a completely different VIN on the IRS letter is actually helpful evidence - it clearly shows something went wrong in the process. When you contact the IRS Clean Vehicle Credit department, emphasize this point first. They can look up that VIN and see who actually owns that vehicle and whether a legitimate transfer was made. A few additional steps to consider: Request a copy of your complete sales file from the dealership in writing (certified mail). Even if they're not responding to calls, they're legally required to provide this in most states. Also, check if your vehicle purchase was financed - if so, the lender may have copies of all the paperwork that was supposed to be signed. One thing that concerns me is the 80-mile distance you mentioned. Dealers operating far from customers sometimes use this distance as a shield against complaints, making it harder for people to follow up in person. This could be part of a pattern if they're doing this to multiple customers. Document every attempt you make to contact them and keep pushing through official channels. The VIN discrepancy alone should be enough to get this resolved in your favor.

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Carmen Ruiz

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This is really helpful insight from someone in the industry! The point about dealers using distance as a shield is something I hadn't considered but makes total sense. If they're doing this to multiple customers, it would explain why they're completely ignoring calls - they're probably hoping people will just give up rather than make the long drive. The suggestion about requesting the complete sales file through certified mail is smart. Even if they don't respond to phone calls, having a paper trail of your requests will be important if this escalates to legal action or regulatory complaints. Plus, if there are other victims, having documented proof of their non-responsiveness could help build a pattern for investigators. I'm curious - in your experience, how common are these VIN mix-ups? Is this something that happens accidentally due to poor record-keeping, or does it usually indicate something more deliberate?

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Need Help: Company changed my work location to a high-tax state in 2022 without telling me - major tax implications!

So here's my situation - I'm completely blindsided and hoping someone can help me figure out what to do next. In January 2022, I transferred to a new department at my current company. Nothing unusual there, and remote work is normal for us. My previous supervisor was in Colorado while I'm based in Tennessee. When I started the new position, my new manager is based in New York. I just discovered while working on my 2025 taxes (for tax year 2024) that payroll has been recording me as a New York employee since the transfer! They never asked me to complete any new tax forms, didn't notify me of the change, and somehow also changed my filing status from Married to Single. I've been living in Tennessee this whole time (which has no state income tax). Meanwhile, they've been withholding New York state taxes at their much higher rates for over two years now! I only discovered this because my Tennessee state tax return looked weird - basically nonexistent compared to previous years. When I dug deeper, I realized all my pay stubs show New York state tax withholding. I've already emailed our payroll department about this mess, but I'm waiting to hear back. What should I expect them to do to fix this? What should I be doing about my tax returns for the past years? Are there any legal issues I should be worried about here? I'm trying to get my head straight before I have more conversations with my employer about this.

QuantumQuest

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Anyone know if this affects social security and medicare withholding too? Or is that the same regardless of which state you're in?

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Social Security and Medicare taxes (FICA) are federal taxes, so they're the same in all states. This issue only affects state income tax withholding. Your federal income tax might be affected if they changed your filing status from Married to Single, though, since that changes your tax brackets.

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This is a frustrating situation but definitely fixable! I went through something similar when my company incorrectly classified me as a California resident while I was actually living in Nevada. A few key things to prioritize: 1. **Document everything** - Save all your pay stubs showing the NY withholding, any emails with payroll, and proof of your Tennessee residency (lease, utility bills, etc.) 2. **Push for W-2c forms** - Don't let payroll just fix it going forward. You need corrected W-2c forms for 2022 and 2023 to properly file amended returns and get your money back. 3. **File non-resident returns** - You'll need to file NY non-resident returns showing $0 NY income to get refunds of the withheld taxes. Since Tennessee has no state income tax on wages, you should get back everything that was withheld. 4. **Check your federal filing status** - The fact that they also changed you from Married to Single could have affected your federal taxes too. Make sure that gets corrected on your W-2c forms. The good news is Tennessee's lack of state income tax makes this cleaner than it could be. You're not dealing with reciprocity agreements or partial credits between states. Just document everything and be persistent with payroll - they created this mess and need to fix it properly.

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Ruby Knight

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I'd strongly recommend reporting the $500 even though it's a small amount. Here's why: the IRS has been increasing their data matching capabilities, and many online platforms are required to report payments to them even if they don't send you a 1099. If you use PayPal, Venmo, CashApp, or similar services, they're now reporting transactions over $600 total per year to the IRS. Even if your feet pic income stays under that threshold, it's better to be transparent. The good news is that for $500 in self-employment income, you likely won't owe any self-employment tax (since that kicks in at $400 net income, and you can deduct legitimate business expenses). You'd just report it as other income on your tax return. My advice: keep detailed records of all transactions, set aside about 20-25% of what you earn for taxes just in case, and consider any expenses you can legitimately deduct (portion of phone/internet bills, any equipment, etc.). Better to over-report than under-report when it comes to the IRS.

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Chloe Harris

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This is really solid advice, especially about the payment platform reporting! I had no idea that PayPal and those other apps were reporting to the IRS now. That definitely changes things - even if the feet pic platform doesn't send a 1099, if the payments go through one of those services, the IRS might still see the income anyway. Better to report it upfront than get caught later. The 20-25% setting aside for taxes is smart too, even if you end up not owing much. Thanks for breaking this down so clearly!

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I've been following this thread and wanted to add something that might help. As someone who works in tax preparation, I see situations like this all the time. The $500 threshold is actually pretty common for people testing out online side gigs. Here's what I tell my clients: even though $500 seems small, reporting it correctly from the start establishes good habits and protects you down the line. The IRS has gotten much better at cross-referencing data from payment processors, social media platforms, and other digital sources. For your specific situation, since you're planning to stop after making $500, you're probably looking at reporting this as "Other Income" on Schedule 1 of your Form 1040, assuming your net earnings stay under $400 after any legitimate business deductions. Keep receipts for anything related to this activity - even small expenses like a portion of your internet bill or phone costs can help reduce your taxable income. The key is documentation. Screenshot every transaction, keep records of any expenses, and track dates. Even if you never get audited, having clean records makes filing so much easier. And honestly, for $500 in additional income, you're probably looking at maybe $50-75 in extra federal taxes depending on your bracket, so it's not going to break the bank. Good luck with the car repair fund!

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Dmitry Popov

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This is incredibly helpful, thank you! As someone who's never dealt with any kind of side income before, it's reassuring to hear from an actual tax professional. The point about establishing good habits makes a lot of sense - even though $500 feels small now, if I ever do other side work in the future, I'll already know how to handle it properly. I really appreciate the specific guidance about keeping screenshots and tracking expenses. I hadn't even thought about deducting things like internet costs. And honestly, knowing it might only be $50-75 in extra taxes makes this feel much more manageable. That's way less scary than I was imagining! One quick question - when you say "portion of internet bill," how do I figure out what portion is legitimate to deduct for something like this?

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