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Connor Murphy

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Just a heads up that NY has some of the most aggressive non-resident income tax policies in the country! If you physically worked in NY, they will definitely want their cut. Make sure you're tracking exactly which days you worked in which state. NY has the notorious "convenience of employer" rule where they might try to tax income you earned while physically in NC if it was for a NY-based company and you were working remotely "for convenience" rather than necessity.

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Yara Nassar

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This! NY's convenience rule screwed me last year. I lived in CT but worked remotely most days for a NY company. NY still taxed all my income even days I never set foot in the state. Definitely check this rule.

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Heather Tyson

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Just went through this exact situation last year with W2s from Texas and Florida! Here's what I learned that might help: 1. Yes, you combine all income ($132k total) on your federal return - that part is straightforward. 2. For state taxes, since NC has income tax but NY has higher rates, you'll likely end up paying some additional tax to NY beyond what was withheld from your NY paychecks. 3. The key thing that saved me money was making sure I understood the timing - if you had taxes withheld from both W2s throughout the year, you might actually get a refund from one state while owing the other. 4. Keep detailed records of your work locations and dates. I used a simple spreadsheet tracking which days I was physically in each state. This becomes crucial if either state audits your return. One thing that really helped was calling both state tax departments early in the process to confirm I understood their specific rules correctly. Each state has slightly different interpretations of multi-state income, and getting it right the first time saved me a lot of headache later. Good luck with your filing!

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Ella Lewis

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This is really helpful, thanks! The timing aspect you mentioned is something I hadn't considered. When you say you might get a refund from one state while owing the other - does that mean the withholdings from each W2 might not match up with what you actually owe each state? Also, did you find any particular challenges with the record-keeping? I'm wondering if I should go back and try to reconstruct my work location calendar from emails and calendar entries, or if that's overkill for a straightforward situation like mine.

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Mei Chen

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This thread has been incredibly informative! I'm also doing tax loss harvesting for the first time this year and had the exact same confusion about the December 31 deadline. One additional consideration I learned from my research: if you're planning to harvest losses but also want to maintain exposure to the market, you might want to consider using the proceeds to immediately buy a similar (but not substantially identical) investment to avoid missing out on potential gains while staying compliant with wash sale rules. For example, if you're selling an individual stock at a loss, you could use those proceeds to buy a broad market ETF, or if you're selling a large-cap growth fund, you might switch to a total market fund temporarily. Just make sure to wait the full 31 days before buying back the original position if you want to avoid wash sale treatment. Thanks everyone for confirming the December 31 trade date rule - that removes a lot of uncertainty from my year-end planning!

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Sunny Wang

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Great strategy on maintaining market exposure while harvesting losses! I'm doing something similar this year. One thing I discovered is that some brokerages actually have built-in tools to help identify "substantially identical" securities to help you avoid wash sales when doing these substitution trades. For anyone else reading this, I'd also recommend checking if your brokerage offers tax loss harvesting previews or calculators - mine shows me exactly how much I could save before I execute the trades, which has been super helpful for planning. The December 31 deadline definitely gives us flexibility, but having a clear strategy like yours for reinvestment makes the whole process much smoother. Thanks for sharing that approach - it's exactly what I needed to hear as I finalize my own year-end tax planning!

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This has been such a valuable discussion! As someone who's been putting off tax loss harvesting because I was confused about the timing, you've all given me the confidence to finally execute my strategy. Just to summarize what I've learned for anyone else who might be reading this: - December 31st is the absolute deadline (trade date, not settlement date) - After-hours trades on 12/31 still count for the current tax year - Watch out for wash sale rules (30 days before/after) - Keep good documentation, especially for last-minute trades - Consider the order of trades (losses first, then gains) - Be mindful of mutual fund distribution dates I'm planning to sell my underperforming positions this week to avoid any last-minute stress, but it's reassuring to know I have until December 31st if needed. The tools mentioned (taxr.ai for analysis and Claimyr for IRS questions) also sound like they could be really helpful resources. Thanks everyone for sharing your experiences and expertise - this community is amazing!

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Evelyn Xu

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This is such a comprehensive summary, thank you! As someone who's been lurking and learning from this thread, I really appreciate how you've organized all the key points. I'm in a similar boat - have been procrastinating on tax loss harvesting because the rules seemed so confusing, but this discussion has cleared up all my major questions. One thing I'm still wondering about: if I'm harvesting losses from individual stocks, is there a minimum holding period I need to worry about? I know there are short-term vs long-term capital gains rules, but does the same apply to losses? Some of my losing positions I've only held for a few months, while others I've had for over a year. Also, does anyone know if the wash sale rule applies if I sell at a loss in my taxable account but my spouse buys the same stock in their IRA around the same time? We file jointly but have separate investment accounts. Thanks again everyone - this has been incredibly educational!

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To add some historical context to this discussion, the authority for the Treasury Department to issue tax regulations comes from 26 U.S. Code Β§ 7805, which gives the Secretary of the Treasury the power to "prescribe all needful rules and regulations for the enforcement" of tax laws. This delegation of authority has been around since the Revenue Act of 1916! Sometimes Congress will specifically direct Treasury to issue regulations on a particular topic. These are called "legislative regulations" and they carry the full force of law. Other times, Treasury issues "interpretative regulations" on their own initiative to clarify how they understand the tax code.

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Does the public get any say in these regulations before they become final? Or do they just get announced and we have to deal with them?

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Yes, the public absolutely gets input! The Treasury Department follows the Administrative Procedure Act, which requires a notice and comment period for most regulations. They publish proposed regulations in the Federal Register, and then anyone can submit comments during a specified period (usually 30-90 days). After reviewing public comments, Treasury then issues final regulations, often with modifications based on the feedback received. Sometimes they'll even hold public hearings on particularly complex or controversial regulations. The IRS also issues Revenue Rulings, Revenue Procedures, and other guidance that help interpret the tax code, though the formal regulation process is the most rigorous.

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Something nobody has mentioned yet is that sometimes courts effectively "write" tax regulations when they interpret ambiguous parts of the tax code or regulations. I had a case where I followed what I thought the regulation clearly stated about rental property depreciation, but my accountant explained that a Tax Court decision had effectively changed how that regulation is applied.

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Emma Wilson

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This is an excellent point! I think the courts use something called the Chevron doctrine when reviewing tax regulations? I vaguely remember learning about this in a business law class - something about courts deferring to agencies like the IRS when the law is unclear?

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Jamal Harris

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You're absolutely right about the Chevron doctrine! Courts generally defer to the IRS's interpretation of tax laws when the statute is ambiguous, as long as the agency's interpretation is reasonable. However, this can create situations where following the written regulation isn't enough - you also need to know how courts have interpreted it in practice. It's frustrating that tax compliance sometimes requires tracking court cases in addition to the actual regulations. Have you found any good resources for staying updated on significant Tax Court decisions that might affect how regulations are applied?

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Slightly off-topic but related - make sure you check if your home country requires you to report your US LLC interest or allows you to claim the losses on your home country tax return! I'm from Australia, and I have to report my US LLC interest on my Australian tax return too, even though I already file a 1040-NR in the US. Some countries treat US LLCs as corporations while others treat them as flow-through entities like the US does. This "hybrid entity" issue can create tax mismatches where losses get trapped in one country.

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Dylan Hughes

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Good point! In the UK we have to file a specific supplementary page for foreign partnerships. My accountant said the losses from my US LLC were basically "trapped" in the US system until the business became profitable, couldn't use them on my UK return at all.

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Aiden Chen

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As someone who went through a similar situation last year, I can confirm what others have said - you absolutely need to file Form 1040-NR even with only losses from your LLC partnership. The filing requirement is triggered by being "engaged in a trade or business in the United States," not by having positive income. One thing I'd add that hasn't been mentioned yet - make sure you keep detailed records of these losses because they become valuable when carried forward. The IRS may ask for supporting documentation in future years when you try to use the losses against profitable income. Also, if your LLC made any estimated tax payments on your behalf during 2024 (which sometimes happens even in loss years for various reasons), you'll want to make sure those are properly reported on your 1040-NR so you can get credit for any overpayments. Check box 16 on your K-1 to see if there were any payments made. The $17,400 loss figure you mentioned should go on Schedule E of your 1040-NR. Don't let the complexity intimidate you - it's a standard filing requirement for non-US persons with US business interests.

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This is really helpful information! I didn't realize about checking box 16 on the K-1 for estimated payments. My LLC partner mentioned something about quarterly payments being made, but I wasn't sure how that would affect my non-resident return since we had losses overall. Quick question - when you say "detailed records," what specific documentation should I be keeping beyond the K-1 itself? Should I be getting copies of the LLC's books and records, or is the K-1 sufficient for future years when I want to use these losses? Also, do you know if there's a deadline difference for non-residents? I know regular taxpayers have until April 15th, but I've heard conflicting information about whether non-residents get until June 15th automatically or if that requires an extension.

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Luca Romano

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Can someone explain what happens if you just put $0 for this question? I've honestly never reported any use tax in my life and I buy stuff online constantly. Never had an issue with my returns. Is the IRS really going to come after me for not tracking every random purchase I make on the internet??

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Nia Jackson

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Technically, you're supposed to pay it, but the reality is that for small amounts, enforcement is practically non-existent. I'm not advocating tax evasion, but most states just don't have the resources to track individual online purchases. They're more focused on big-ticket items and business purchases.

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I totally get the confusion! I went through the same thing last year. Here's what I learned: that question is basically asking about "use tax" - which is what you owe on purchases where the seller didn't collect sales tax from you. Don't stress too much about tracking every single purchase perfectly. Most states know this is unrealistic for regular people. Here's what I'd suggest: 1. Check if your state offers a "safe harbor" amount - this is usually a flat fee based on your income that you can pay instead of calculating exact amounts 2. Focus on any big purchases you made from smaller online retailers (especially out-of-state ones) 3. Major retailers like Amazon usually collect sales tax everywhere now, so those probably aren't an issue For this year's filing, if you can't track everything perfectly, most people either use the safe harbor amount or make a reasonable estimate. The key is being honest and making a good faith effort. You're definitely not alone in finding this confusing - it's one of those tax questions that trips up tons of people!

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LordCommander

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This is really helpful advice! I'm in the same boat as the original poster and had no idea about the "safe harbor" option. Do you know where I can find out what my state's safe harbor amount is? I'm guessing it varies by state? Also, when you say "reasonable estimate" - do you have any tips on how to come up with a number that won't raise red flags but also isn't totally random?

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