Wait I'm confused about something. If I'm a substitute teacher working directly for a school district, wouldn't I be a W-2 employee not a 1099 contractor? I subbed last year and got a W-2.

Great question! As others have mentioned, you should receive a 1099-NEC from the learning center if they paid you $600 or more. But here's something important to keep in mind - the classification itself matters a lot. If the learning center was controlling your schedule, providing lesson plans, telling you exactly how to teach, or treating you like other employees, you might have been misclassified. True independent contractors have more control over how they do their work. This is especially common in education where companies try to avoid paying employment taxes and benefits. If you believe you were misclassified, you can file Form SS-8 with the IRS to get an official determination, or Form 8919 when you file your taxes to pay only the employee portion of Social Security and Medicare taxes instead of the full self-employment tax. This could save you money since self-employment tax is about 15.3% versus 7.65% for employees (the employer pays the other half). Just something to consider as you're navigating this for the first time!

This thread has been incredibly enlightening! I'm a dual US/Greece citizen who just moved to Athens last month and I'm already stressing about next year's tax situation. One thing I haven't seen mentioned is the complexity around Greek social security contributions. Since I'm self-employed with US clients (similar to the original poster), I'm trying to figure out if I need to pay into the Greek social security system (EFKA) on top of everything else we've discussed here. From what I've read, Greece requires self-employed residents to contribute to their social security system regardless of whether they're also paying US self-employment taxes. Has anyone dealt with this? The contribution rates seem pretty high (around 20% from what I've seen) and I'm not sure if there's any treaty relief for double social security taxation. Also, does anyone know if Greek social security contributions are deductible on your US tax return? I'm trying to budget for 2025 and between US taxes, Greek income taxes, and potentially Greek social security, I'm worried I'll be paying close to 50% of my income in various taxes and contributions! Any insights would be hugely appreciated - this community has already saved me from making some costly mistakes before I even start filing!

This is such a comprehensive discussion! As someone who's been dealing with dual US/Greece taxation for about 3 years now, I wanted to add a few practical tips that might help newcomers avoid some common pitfalls: **Documentation is everything** - Keep detailed records of all your US tax payments, including quarterly estimated payments. Greece will want to see proof of taxes actually paid, not just what was owed. I learned this the hard way when they initially rejected my foreign tax credit claim because I only provided my tax return, not proof of payment. **Exchange rates matter more than you think** - Use the IRS published exchange rates for converting your Greek income to USD for US filing, and use the European Central Bank rates for converting US taxes to euros for Greek filing. Consistency is key, and using "official" rates helps if either country questions your calculations. **Consider the timing of estimated payments** - Since you're paying US estimated taxes throughout the year but filing Greek taxes after the year ends, you might want to slightly overpay your US estimates. This gives you more foreign tax credits to claim in Greece and reduces the risk of owing a large lump sum to Greece at filing time. **Professional fees are worth it** - I spent about €800 last year on a dual-taxation specialist, but they saved me over €2,500 in unnecessary taxes and penalties. The complexity isn't worth trying to handle alone, especially in your first few years. Hope this helps others navigate this maze a bit more smoothly!

Don't forget to consider state taxes too, not just federal! I paid off my federal taxes from my old LLC but completely overlooked the state tax debt. When I went to register my new LLC, I discovered my state (California) wouldn't let me form a new business entity until I cleared the old tax debt with the state franchise tax board. Had to delay my launch by 2 months while dealing with that mess. Different states have different rules, so check your specific state's requirements before spending money on new LLC formation.

This is such a common situation for entrepreneurs trying to get back on their feet! I went through something similar when my consulting LLC failed in 2022 and I owed about $8,500 in back taxes. The good news is that you absolutely can form a new LLC while owing taxes from your old one - the IRS doesn't block business formation. However, you need to be strategic about it. The key things I learned: 1. Set up your new LLC properly with completely separate finances - different bank, different EIN, clear documentation of startup capital 2. Address the old debt proactively rather than ignoring it - even a basic installment agreement shows good faith 3. Keep detailed records showing the two businesses are completely separate entities I ended up calling the IRS (after many failed attempts) to set up a payment plan for the old debt before launching my new business. It gave me peace of mind and prevented any collection actions that could have interfered with getting business banking or credit for the new venture. The worst thing you can do is try to hide from the old debt - it won't go away and could create bigger problems down the road. But don't let it stop you from pursuing your new business opportunity either!

I've been through a similar CP2000 nightmare and want to share what worked for me. First, definitely try calling for an extension like others mentioned - I got 60 extra days just by explaining I needed more time to gather documentation. But if you can't get through or they deny the extension, here's what saved me: I sent a detailed response letter with partial agreement, paying only the portion I absolutely knew was correct (about 40% of their revised amount). In the letter, I clearly stated "I disagree with the following adjustments" and listed each disputed item with supporting documentation. The key is being very specific about what you agree with versus what you're disputing. Don't just say "I disagree with the assessment" - break it down line by line. This shows the IRS exactly where to focus their review and demonstrates you're not just stalling. I also sent everything certified mail with return receipt to prove they received it before the deadline. Three months later, they sent me a revised notice that was actually $800 in my favor! The whole process took about 6 months total, but I avoided paying money I didn't owe and didn't have to deal with amended returns later. The deposit option mentioned by Aisha is also brilliant - wish I had known about IRC 6603 deposits when I was dealing with mine!

Based on everyone's advice here, I think I'm going to try a combination approach. First, I'll call tomorrow morning to request an extension using that Claimyr service since several people had success with it - even Nia who was initially skeptical came back to say it worked. If I can get the extension, perfect - that buys me time to properly dispute everything. But if not, I'm going to send a partial agreement letter with an IRC 6603 deposit for the portion I know is definitely correct (probably around $3,000-4,000 of the $7,000). This way I stop penalties and interest on most of it while preserving maximum flexibility to recover anything I shouldn't owe. I really appreciate the specific advice about being line-by-line in the dispute and using certified mail. The memo line tip about writing "PARTIAL PAYMENT - SEE ATTACHED CORRESPONDENCE" is exactly the kind of detail I needed to know. One last question - has anyone here actually used the IRC 6603 deposit option successfully? I want to make sure I get the language exactly right in my letter since this seems like the safest approach given my tight timeline.

Just a quick tip from someone who's been in financial services for 20+ years - check if these accounts have automated dividend reinvestment plans (DRIPs). When dividends are automatically reinvested, the cost basis often equals proceeds because the purchase price equals the sale price at that exact moment. If the account is high value ($1M+) and has been running on autopilot with DRIP for years, you can absolutely get these massive matching numbers. The tiny fractional differences might not even show up due to rounding on the 1099-B.

This is a great discussion with lots of helpful insights! I'm seeing similar patterns with some of our clients and wanted to add one more scenario I've encountered recently. Sometimes matching proceeds and cost basis can result from mutual fund exchanges within the same fund family. When clients do tax-free exchanges between funds (like moving from a growth fund to a value fund within the same company), the basis often transfers directly, resulting in identical numbers on the 1099-B. Also, for anyone dealing with these complex situations regularly, I'd recommend keeping a detailed spreadsheet tracking which clients have these matching figures and the eventual explanations. It's helped me identify patterns - for instance, I noticed that three clients with matching basis/proceeds all had the same financial advisor who was implementing a specific tax-loss harvesting strategy. The key is definitely not to panic when you see these numbers. There are legitimate reasons, but it's always worth investigating to make sure you're handling the tax implications correctly for your clients.