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I've been dealing with wash sales for years as an active trader, and one thing that really helped me was setting up a spreadsheet to track all my positions across different accounts. The cross-account wash sale issue that someone mentioned is absolutely real and can catch you off guard. One strategy I use is the "parking" method - instead of immediately repurchasing the same stock after a loss sale, I'll buy a similar ETF or a stock in the same sector for 31+ days, then switch back if I want. For example, if I sell AAPL at a loss, I might buy QQQ or MSFT temporarily to maintain similar market exposure without triggering the wash sale. Also, be extra careful with dividend reinvestment plans (DRIPs). If you have automatic dividend reinvestment turned on and it buys shares within 30 days of your loss sale, that can trigger a wash sale too. I learned this one the hard way when my "clean" loss harvesting got messed up by a $12 dividend reinvestment I forgot about. The basis adjustment works exactly as others described, but tracking it manually across multiple securities and years can get messy quickly. Good record keeping is essential!

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CyberNinja

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This is incredibly helpful advice! I never thought about DRIPs potentially triggering wash sales - that's such a sneaky gotcha that could mess up careful tax planning. The "parking" strategy sounds smart too. Do you have any specific recommendations for similar ETFs that work well for this? For instance, if I'm holding individual tech stocks, would switching between QQQ and VGT be different enough to avoid the substantially identical rule, or do I need to go broader like VTI? Also, I'm curious about your spreadsheet setup - do you track this manually or have you found any tools that can automatically pull in data from multiple brokerages? Managing this across several accounts sounds like a lot of work but seems essential for anyone doing active tax loss harvesting.

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Bruno Simmons

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Great point about DRIPs! I had no idea those could trigger wash sales too. For the "parking" strategy with tech stocks, I've had good success with these pairings: - Individual tech stocks β†’ QQQ or VGT (both should be different enough) - QQQ ↔ VGT (these track different indexes so definitely safe) - Individual stocks β†’ broader market ETFs like VTI or SPY - Large cap growth β†’ small cap value ETFs for maximum differentiation The key is making sure the securities aren't "substantially identical." Individual stocks vs ETFs are almost always safe, and ETFs that track different indexes (even in similar sectors) should be fine. For tracking across accounts, I use a combination of approaches: - Manual CSV downloads from each brokerage monthly - A Python script I wrote that parses the files and flags potential wash sales - Portfolio tracking tools like Personal Capital for the big picture view The manual work is tedious but I've found it's worth it. Missing just one cross-account wash sale can cost you hundreds in lost tax benefits. Plus, the discipline of tracking everything has made me a much more strategic trader overall. Have you run into the IRA wash sale issue mentioned earlier? That's another nasty gotcha where losses can be permanently disallowed.

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Ravi Patel

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The wash sale rule is definitely one of the most misunderstood aspects of tax law! Your $250 loss isn't gone forever - it gets added to the cost basis of your remaining shares (LOT A). What's happening is that your LOT A basis increases from $2,000 to $2,250 total, so when you eventually sell those shares, you'll realize that loss through either a smaller gain or larger loss on the sale. The tricky part you identified is correct though - since LOT A was purchased 980 days before the wash sale occurred, those shares are already long-term. This means your short-term $250 loss effectively gets converted into a long-term loss when you eventually sell LOT A. This is actually a common "gotcha" that can hurt your tax planning since short-term losses are generally more valuable (they offset ordinary income rates vs capital gains rates). One thing to watch out for: if you're using Tax Sensitive method specifically to harvest losses, make sure you're planning around the 30-day wash sale window. Consider waiting 31+ days before repurchasing, or temporarily "parking" your money in a similar but not substantially identical security (like a related sector ETF) to maintain market exposure while avoiding the wash sale. The software conflicts you're seeing probably stem from different interpretations of how to track basis adjustments across multiple lots with different accounting methods. When in doubt, the IRS Publication 550 examples are your best reference.

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For your wife's nanny income, wouldn't she need to pay self-employment tax too? That's an extra 15.3% on top of regular income tax, right? That seems like it would be a big hit on back taxes you're already struggling with.

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Oh that's a huge relief! I've been reporting babysitting money as self-employment income and paying that extra tax for years. So if I'm caring for kids in their home and following their schedule, I'm actually a household employee and not self-employed? How would I fix my past returns then?

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Millie Long

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Yes, you're likely correct about being a household employee! The key test is whether you're working in their home, following their schedule, and they control how you do your work. If so, you're their employee, not self-employed. To fix past returns, you'd need to file amended returns (Form 1040X) for any years within the statute of limitations (generally 3 years). You'd remove the self-employment income from Schedule C and instead report it as "other income" on Schedule 1. This should eliminate the self-employment tax you've been paying. However, keep in mind that your employers technically should have been paying their share of Social Security and Medicare taxes too. When you amend, you might want to consider whether this could create issues for them, similar to what @Makayla Shoemaker is dealing with regarding her cousin s'family. You might want to consult with a tax professional to make sure you handle the amendments correctly and understand all the implications before filing.

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Amara Eze

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Just wanted to add my perspective as someone who went through a similar situation with back taxes and missing documentation. The advice about reporting the nanny income as "other income" on Schedule 1 is spot on - that's exactly what I did when I had unreported cash payments from years ago. One thing that really helped me was creating a simple spreadsheet showing how I estimated the income. I listed things like "worked approximately 20 hours/week from March-December 2018 at $15/hour" with whatever details I could remember. Even if it's not perfect, the IRS appreciates seeing that you made a good faith effort to be accurate. Also, don't stress too much about the payment plan approval. In my experience, the IRS is pretty reasonable about setting up installment agreements, especially when you're proactively trying to get caught up. The fact that you've already filed 2019-2023 shows you're making an effort to stay compliant going forward. Filing jointly is almost certainly going to be better than separately - you'll get a higher standard deduction and potentially qualify for credits you'd lose filing separately. Just get that 2018 return filed with your best estimate and move forward with getting current.

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Nina Chan

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Have you checked the calculators on Fidelity or Vanguard's websites? I've found both to be pretty accurate for SEP IRA calculations. The Fidelity one in particular lets you input your self-employment income and automatically does all the adjustments for you. I've been using it for the past three years and the numbers always match what my tax software calculates later.

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I tried the Vanguard one but got confused by some of the terminology they use. Does anyone know if the SE income they ask for is before or after business expenses? And do these calculators account for that reduction factor people mentioned above?

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Nina Chan

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The SE income they ask for is your net profit from Schedule C - so that's after all your business expenses. And yes, both Vanguard and Fidelity's calculators do account for the reduction factor - they're calculating the actual 25% of your compensation after adjustments, not the simplified 20% rule of thumb. Most people get confused because the true formula is a bit circular (since your contribution impacts the base it's calculated on), but these big financial institutions have accurate calculators. Just make sure you're entering your net profit from self-employment, not your gross receipts!

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Ruby Knight

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I'm an accountant and I made a simple Excel calculator for SEP IRA contributions for my clients. It's nothing fancy but it gets the job done. It includes the adjustment for self-employment tax and handles the circular calculation accurately. I'd be happy to share it if you DM me. No charge obviously, just pay it forward somehow!

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Could you maybe explain how the circular calculation actually works? I've been trying to understand it but getting confused. Is it because the SEP contribution itself reduces the income that the 25% is based on?

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Exactly right! The circular calculation happens because your SEP IRA contribution is technically a business deduction that reduces your net self-employment income, which in turn affects the base amount your 25% contribution limit is calculated on. So if you try to calculate it step by step: your contribution = 25% of (net SE income - SEP contribution). You can see the problem - you need to know the contribution amount to calculate the contribution amount! The IRS solves this with a specific formula that works out to approximately 20% of your Schedule C net profit for most people. Ruby's Excel calculator probably uses the exact IRS formula from Publication 560 to handle this automatically. It's one of those things that's way easier to let a calculator or software handle than to work through manually every time.

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Welcome to the US tax system! Your situation is actually pretty common for new green card holders. Just wanted to add a couple of practical tips from my own experience with international transfers: 1. When you do transfer the money, consider doing it in smaller chunks (like $7k-8k at a time) rather than all $21k at once. This won't change your tax obligations, but it can sometimes get you better exchange rates and lower transfer fees depending on your banks. 2. Make sure to get a detailed transfer receipt showing the exchange rate used and any fees charged. These can be useful for your records, especially if you need to document the transaction later. 3. If your German bank charges high fees for international transfers, definitely look into services like Wise or Remitly - they often save hundreds of dollars on large transfers like yours. The good news is that Germany has a tax treaty with the US, so if you did have any taxable income from interest on that account while you were a US resident, you could potentially claim foreign tax credits to avoid double taxation. But for the principal amount you earned while working there, you're all set - no US taxes owed on the transfer itself!

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Luca Esposito

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Great advice about breaking up the transfer! I did something similar when I moved my savings from Australia - ended up saving almost $300 in fees by using Wise instead of my bank's wire transfer service. One thing to add though: make sure you keep track of all the individual transfer amounts and dates for your records. Even though it doesn't create additional tax obligations, having a clear paper trail is always helpful if questions come up later during audits or immigration processes. Also, since you mentioned the Germany-US tax treaty, that's definitely worth understanding even though your principal won't be taxed. If your German account earned any interest while you were already a US resident (even just for those 3 months), you'd need to report that interest income on your US tax return. But you can often claim a foreign tax credit for any German taxes withheld on that interest, so you shouldn't end up paying twice on the same income.

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Kai Santiago

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Just wanted to share my experience as someone who went through a very similar situation last year. I moved from Canada to the US with about $35k in savings and was equally confused about the tax implications. The key thing that helped me was understanding the difference between "pre-immigration assets" (money you earned before becoming a US tax resident) and income earned after you become subject to US taxation. Your $21k from working in Germany falls into that first category, so transferring it won't create a US tax liability. However, I'd strongly recommend keeping very detailed records of everything - not just for the FBAR filing, but also in case you ever need to prove the source of funds during future immigration processes or if the IRS has questions. I kept copies of my Canadian employment contracts, tax returns from Canada showing the income was properly reported there, and bank statements showing the money sitting in my account before I moved to the US. One practical tip: when I made my transfer, I used a combination of Wise for the bulk amount and kept about $5k in my Canadian account initially. This way I could test the process with a smaller amount first and also had some buffer time to make sure I understood all the US reporting requirements before moving everything over. The whole process ended up being much less scary than I initially thought, but having good documentation made me feel much more confident about everything!

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Nia Wilson

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Something nobody's mentioned yet - check if the foreign country has a tax treaty with the US! This makes a huge difference. I invested in a UK company and because of the tax treaty, my dividend tax rate was reduced from 30% to 15%. Also - watch out for foreign currency gains/losses. The IRS treats these as separate taxable events from your actual investment return. My tax software totally missed this and I had to file an amended return last year.

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Aisha Hussain

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Would using a specialized accountant for this be worth it? I'm getting a headache just thinking about tracking all these foreign investment rules.

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Jamal Edwards

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Yes, you absolutely need to track exchange rates on the specific dates of each transaction - dividend receipts, stock purchases, sales, etc. The IRS requires you to convert everything to USD using the exchange rate from that specific date. I use the Treasury's daily exchange rates from their website to stay consistent. For record-keeping, I created a simple spreadsheet with columns for date, transaction type, foreign currency amount, exchange rate, and USD equivalent. It's tedious but necessary. Some tax software can help automate this if you input the foreign currency amounts. @37b3aea8aa57 A specialized international tax accountant is definitely worth it if your foreign investments are substantial or complex. The rules are intricate and the penalties for mistakes can be severe. I learned this after nearly missing several required forms in my first year of foreign investing.

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Emily Parker

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One important aspect that hasn't been covered yet is the timing of when you recognize income for tax purposes. For foreign investments, you need to be aware of the "constructive dividend" rules that can apply even when no actual cash distribution occurs. If you're investing in a European company as mentioned, also consider whether it's structured as a corporation, partnership, or other entity type under both US and foreign tax law. Sometimes an entity that's treated as a corporation abroad might be considered a partnership for US tax purposes, which completely changes your reporting obligations. Also worth noting - if you're planning to hold this investment long-term, consider the impact on your estate planning. Foreign investments can complicate estate tax filings significantly. The reporting requirements don't go away just because you're not actively managing the investment anymore. I'd strongly recommend getting that consultation with a tax attorney who specializes in international taxation before making the investment, not after. The structure you choose upfront can make a huge difference in your ongoing tax compliance burden.

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Jenna Sloan

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This is really helpful advice about getting professional help upfront! I'm curious about the "constructive dividend" rules you mentioned - could you give an example of when that might apply? I want to make sure I understand what situations could trigger tax obligations even without receiving actual cash. Also, when you mention entity classification differences between US and foreign tax law, does that mean I need to research how the European company is structured under both tax systems before investing? That sounds incredibly complex for what I thought would be a straightforward investment.

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Natalie Adams

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@c6da548b9fab Great point about the constructive dividend rules! A common example would be if you own shares in a foreign corporation that uses its profits to provide you with personal benefits - like paying for your travel expenses or letting you use company property for personal purposes. Even though you didn't receive cash, the IRS treats the value of those benefits as taxable income. Another scenario is when a foreign corporation makes loans to its shareholders at below-market interest rates, or forgives debts owed by shareholders. These can be treated as constructive dividends even without any cash changing hands. Regarding entity classification - yes, you absolutely need to understand how the entity is treated under both tax systems. For instance, many European limited liability companies are treated as corporations under their local tax law but might be classified as partnerships or disregarded entities for US tax purposes. This "check-the-box" election can dramatically change your reporting requirements and when you owe US taxes on the entity's income. The complexity is exactly why getting professional advice before investing is so crucial. What seems like a simple stock purchase can trigger incredibly complex reporting requirements depending on the structure.

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