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I work as a massage therapist and see a lot of clients who get regular treatments for work-related injuries like yours. From what I've observed with my clients who've successfully deducted these expenses, the key is really about establishing that medical necessity piece. A few things I've noticed that help clients with their documentation: Make sure you're seeing a licensed massage therapist (LMT) rather than someone at a spa - the IRS looks more favorably on treatments from licensed healthcare providers. Also, ask your therapist to note in their records the specific work-related conditions being treated and how the massage therapy addresses those issues. One strategy I've seen work well is to have your first few sessions specifically focused on assessment and treatment planning. A good LMT should be able to document the specific muscle tension patterns, postural issues, and movement restrictions caused by your barbering work, then create a treatment plan showing how regular massage addresses these occupational health issues. This creates a paper trail that goes beyond just "I get massages for back pain" to "I receive therapeutic massage as part of a documented treatment plan for occupational injuries caused by the repetitive motions and sustained postures required in my profession." The documentation piece really can make or break these deductions during an audit, so it's worth investing in that professional relationship with a licensed therapist who understands the tax implications.

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Aaron Boston

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This is incredibly helpful insight from someone who actually works in the field! I never thought about the difference between a licensed massage therapist versus spa treatments, but that makes total sense from an IRS perspective. The treatment plan approach you mentioned sounds like it could really strengthen the case for deductibility. Having that professional assessment documenting how specific barbering motions (like the repetitive arm movements, prolonged standing, and neck positioning) are directly causing the muscle issues would create exactly the kind of paper trail that could withstand scrutiny. Do you know if most LMTs are familiar with creating this kind of documentation for tax purposes? Or is this something I'd need to specifically request and explain when I'm looking for a therapist? I want to make sure I find someone who understands both the therapeutic side and the documentation requirements. Also, would it be beneficial to have my regular doctor refer me to the massage therapist, or is it sufficient to just start with a licensed LMT directly? I'm trying to figure out the strongest way to establish that medical necessity chain from the beginning.

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GalacticGuru

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@d50f9aae8163 Most licensed massage therapists are familiar with documentation requirements, especially those who work with healthcare referrals, but it's definitely worth mentioning upfront that you'll need detailed records for tax purposes. When you're looking for an LMT, ask specifically about their experience with work-related injuries and whether they're comfortable providing documentation that establishes medical necessity. Having a doctor's referral can definitely strengthen your case, especially if your doctor can document the occupational nature of your injuries and specifically recommend massage therapy as treatment. This creates a clear medical chain: doctor diagnoses work-related musculoskeletal issues β†’ doctor recommends massage therapy β†’ licensed therapist provides treatment and documents progress. However, you can also start directly with an LMT who specializes in occupational injuries. Many are trained to do initial assessments and can provide the documentation you need. The key is finding someone who understands they're not just providing relaxation services, but actual therapeutic treatment for documented conditions. Either path can work, but the doctor referral route might give you extra credibility if you ever face questions from the IRS. Plus, if you haven't had a proper medical evaluation of your work-related back and shoulder issues, it's probably worth doing anyway for your long-term health.

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Lucas Kowalski

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As someone who's been through a similar situation with work-related physical therapy deductions, I want to emphasize how important it is to get ahead of this documentation-wise. I made the mistake of trying to claim expenses retroactively without proper medical backing and it became a nightmare during my audit. Here's what I wish I'd known from the start: Even if you're just starting to consider massage therapy, go to your doctor FIRST and get a proper evaluation of your work-related injuries. Have them document how your barbering work is causing these specific musculoskeletal issues. This creates a medical foundation that supports everything else. When they recommend massage therapy (and they likely will for your situation), make sure it's written as a prescription or formal recommendation, not just a casual suggestion. This distinction matters a lot to the IRS. Also, consider seeing if your state has any workers' compensation or occupational health resources that might help cover some of these costs. Some states have programs specifically for repetitive stress injuries in service professions like barbering. Even if they don't cover massage directly, having official recognition of your condition through these programs can strengthen your tax case. The $2,000+ annual cost is significant enough that it's worth spending a little time and money upfront to document everything properly rather than risk having to pay it all back with penalties later. Trust me on this one - I learned the hard way!

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Chloe Martin

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Does anyone know if I can still contribute to an IRA for 2024 at this point to reduce my tax bill? Or is that deadline passed too?

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The deadline for IRA contributions for a tax year is always the original tax filing deadline (usually April 15 of the following year), regardless of whether you file for an extension or file late. So unfortunately for 2024 taxes, that deadline passed in April 2025. You can still make IRA contributions now, but they'll count toward the 2025 tax year.

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Douglas Foster

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Don't panic! You're actually in a pretty good position since you mentioned you'll likely get a refund. Here's what you need to do: 1. **File ASAP using regular 2024 tax forms** - no special "late" forms needed 2. **No penalties if you're getting a refund** - the IRS only penalizes when you owe them money 3. **You have until April 2027** to claim your 2024 refund, so while late, you're not in danger of losing it For your situation with all the life changes (divorce, moves, job change), make sure you have: - All W-2s from your various employers in 2024 - Any 1099s if you had contract work - Documentation of moving expenses if they're deductible - Divorce-related tax document changes The IRS is surprisingly understanding about life circumstances causing late filing when refunds are involved. Just file normally and you'll get your refund, though it will take longer to process than if you'd filed on time. The most important thing is to not put it off any longer!

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Mia Rodriguez

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Welcome to the community! This has been such a valuable thread to read through as someone who's also navigating forex tax complexities for the first time. To answer your question about currency conversion for international transactions - the Section 1256 election specifically applies to your trading gains and losses from forex contracts, not to incidental currency conversions from regular international transactions (like business expenses or personal purchases abroad). Those types of conversions typically still fall under general Section 988 rules regardless of your trading election. However, the line can get blurry if you're doing frequent international business transactions alongside your trading activity. This is actually another great reason to speak with an IRS agent through that Claimyr service mentioned earlier - they can help clarify how to properly separate your trading activity from other foreign currency transactions. One additional tip I'd add from my own research: when you do make your Section 1256 election for 2025, consider also documenting your trading strategy and typical holding periods in that internal memo. Some tax professionals recommend this to help establish that your election is consistent with your actual trading approach, which can be helpful if you're ever questioned about the appropriateness of the election. The level of detail and real-world experience shared in this thread has been incredible - definitely saving this post for future reference!

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StarStrider

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Thanks for the clarification on currency conversions! That distinction between trading gains and incidental international transactions makes a lot of sense, but you're absolutely right that the line could get blurry in practice. I really appreciate the tip about documenting trading strategy in the election memo too. That's the kind of forward-thinking detail that could really help if there are ever questions down the road. It shows you made a thoughtful, informed decision rather than just picking whichever option seemed better after the fact. As a newcomer to both forex trading and this community, I'm honestly amazed at how helpful everyone has been in breaking down these complex tax issues. When I first started trading, I naively thought the tax part would be straightforward - just report gains and losses, right? This thread has been a real eye-opener about how much planning and documentation is actually required to do this correctly. I'm definitely going to start preparing my Section 1256 election documentation now for 2025, even though it's still months away. Better to have everything properly set up than scramble at the last minute like I'm doing now for my 2024 filing. @Mia Rodriguez - thanks for the warm welcome and the additional insights! This community seems like an incredible resource for navigating these types of complex tax situations.

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Lara Woods

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As a tax professional who specializes in trader taxation, I wanted to jump in and clarify a few important points that have come up in this excellent discussion. First, regarding the Section 1256 election timing - while it's true you generally need to make the election before January 1st or before beginning trading, there's actually a lesser-known provision that allows you to make the election up until the original due date of your return (without extensions) for the first year you engage in forex trading. This could potentially help some newcomers who weren't aware of the election requirement. Second, I want to emphasize the importance of the "trader tax status" determination alongside your 988/1256 election. If you qualify for trader tax status (which requires substantial, regular, and continuous trading activity), you get additional benefits like deducting trading expenses above the line and potentially qualifying for the mark-to-market election under Section 475. The combination of trader status + Section 1256 election can be incredibly powerful for active forex traders. But qualifying for trader status requires meeting specific IRS criteria about the scope and frequency of your trading activity. For those using the AI tools and IRS callback services mentioned here, make sure to also ask about trader status qualification - it's a separate but related consideration that could significantly impact your tax strategy. The documentation requirements are strict, so proper record-keeping from day one is essential. Keep up the great discussion - this is exactly the kind of detailed tax planning that can save traders thousands of dollars!

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Zara Malik

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This is incredibly valuable information, thank you for sharing your professional expertise! I had no idea about the provision allowing the election up to the original due date for first-year forex traders - that could be a game-changer for people like me who didn't know about the election requirement beforehand. The trader tax status angle is completely new to me as well. Could you elaborate a bit on what "substantial, regular, and continuous" trading activity looks like in practice? I'm doing maybe 15-20 forex trades per week on average - would that potentially qualify, or does it require even more activity? Also, when you mention the mark-to-market election under Section 475, how does that interact with the Section 1256 election? Can you have both, or do you need to choose between them? As someone just starting to understand these complexities, having a tax professional's perspective on the strategic combinations is extremely helpful. The potential tax savings seem significant, but the compliance requirements sound quite demanding too. @Lara Woods - thank you for taking the time to share these insights with the community! This level of professional guidance is exactly what many of us need to navigate these decisions properly.

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Has anyone used TurboTax to file with a Schedule SE? I'm in the same boat with the line 7/8 confusion and wondering if it handles all this automatically or if I need to understand it to input things correctly.

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I use TurboTax Self-Employed and it handles Schedule SE automatically. You just answer questions about your business income and expenses and your W-2 job, and it figures out all the calculations behind the scenes. It even explains these limits if you click the "explain this" links.

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I had the exact same confusion when I started my freelance writing business! The $147k on line 7 threw me off completely - I thought it was somehow related to my actual income too. What really helped me understand it was thinking of it this way: the IRS sets a yearly limit on how much income gets hit with Social Security tax. For 2024, that limit was $147,000. So line 7 is just showing you what that limit is for the tax year. Line 8 is where you put your regular job wages that already had Social Security tax taken out. This prevents you from paying Social Security tax twice if your combined W-2 and self-employment income goes over that $147k limit. Since you mentioned you have a weekend photography gig, you probably also have a regular job. Make sure to put those W-2 wages on line 8 - it could save you money on your self-employment tax calculation!

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Nora Brooks

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This is such a great way to think about it! I'm also new to freelance work (just started doing social media management on the side) and was completely baffled by Schedule SE. The idea of it being a "yearly limit" rather than anything related to my actual earnings makes it click. I was stressing that I somehow owed taxes on $147k when I only made like $8k from my side gig! Question though - if my W-2 job already withholds Social Security tax and I put those wages on line 8, does that mean I might pay less self-employment tax on my freelance income? Or does it work differently?

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Do Robinhood wash sale rules apply differently to options trading?

Hi everyone, wanted to get some insight on a frustrating tax situation with my options trades. I'll simplify the numbers to make this easier to understand. Last year I made around $110,000 trading stock options on Robinhood, with a cost basis of approximately $125,000. My total wash sales according to Robinhood are about $5,000, giving me a net loss of around $8,000. But because of these wash sales, instead of reporting the full $8k loss, they're only showing a $3k loss on my 1099. Most of these wash sales were from day trading options contracts that I either sold at a loss or that expired worthless. I've already contacted Robinhood support and they just told me to "talk to a tax professional" (super helpful, right?). I'm planning to speak with my buddy's wife who does tax work, but thought I'd check here first. I'm particularly confused about one stock - PYPL. I never repurchased the PYPL options that triggered the wash sale, yet Robinhood didn't adjust my cost basis for my existing stock position. Even weirder, the total contract profit/loss for PYPL shows $0.00, which makes no sense. When I asked about this, the customer service rep just said "someone would look into it"... My main question: With stocks, I know you can trigger a wash sale but still claim the loss if you sell the position and don't rebuy within 30 days. But with options, can you permanently lose the tax deduction by triggering a wash sale? Does Robinhood handle this correctly?

Finnegan Gunn

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I've been dealing with similar issues with Robinhood's options wash sale reporting. One thing that helped me understand the problem better was pulling my own trade history and manually calculating what should and shouldn't be wash sales based on the IRS criteria. For options, the key factors are: same underlying stock, same strike price, AND same expiration date. If any of these differ, there's a strong argument that they're not "substantially identical." However, Robinhood's system seems to flag anything with the same underlying as a potential wash sale, which is overly broad. In your PYPL case, if you never repurchased options with identical terms within the 30-day window, those definitely shouldn't be wash sales. The $0.00 profit/loss display is almost certainly a system glitch - I've seen this happen when their automated calculations get confused by expired contracts. My advice: Document everything with specific transaction dates and contract details. When you contact support, reference the specific IRS Publication 550 language about "substantially identical securities" and ask them to review each flagged transaction individually rather than relying on their automated system. It's frustrating, but the squeaky wheel gets the grease with Robinhood. Keep escalating until you reach someone who actually understands options taxation rather than just reading from a script.

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Amara Adebayo

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This is really helpful advice! I'm new to options trading and had no idea about the specific criteria for "substantially identical" securities. I've been getting wash sale flags on what seem like completely different contracts just because they're for the same underlying stock. Quick question - when you say "same expiration date," does that mean the exact same expiration, or would weekly options vs monthly options for the same week potentially be considered different? I've been trading both SPY weeklies and monthlies and I'm wondering if that affects the wash sale treatment. Also, has anyone had success citing IRS Publication 550 specifically when dealing with Robinhood support? I'm wondering if mentioning specific tax code sections actually helps or if their first-level support just ignores it.

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Great question about the expiration dates! Yes, it needs to be the exact same expiration date for the IRS to consider options "substantially identical." So SPY weeklies expiring on Friday and SPY monthlies expiring that same Friday would be considered the same, but weeklies vs monthlies with different expiration dates would not trigger wash sales. Regarding citing IRS Publication 550 - it definitely helps, but you need to get past the first-level support. The initial chat representatives usually don't understand tax regulations and will just give you generic responses. However, once you get escalated to their tax specialist team (which you can request specifically), mentioning Publication 550 Section 4 about wash sales and providing the specific language about "substantially identical securities" carries a lot more weight. I'd recommend having the exact quote ready: "Substantially identical securities include the same stock in the same corporation." For options, this has been interpreted to require same underlying, strike, AND expiration. The more specific you can be with regulatory citations, the more likely they are to take your case seriously and actually review the transactions rather than just defending their automated system. One tip: when you escalate, specifically ask to speak with someone who handles "complex options taxation issues" rather than general customer service. That usually gets you routed to someone with actual knowledge of these rules.

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I've been following this thread closely as I'm dealing with a similar situation. Just wanted to add another perspective on the "substantially identical" issue that might help others. I had a case last year where I was trading AAPL options - sold some $150 calls expiring in March at a loss, then bought $155 calls expiring in April within the wash sale period. Robinhood flagged this as a wash sale, but when I challenged it, they eventually agreed it shouldn't have been flagged since both the strike price AND expiration date were different. The key insight I learned from my tax attorney is that the IRS applies the "substantially identical" test very strictly for options. Even a $5 difference in strike price or one day difference in expiration is enough to make them NOT substantially identical. This is different from stocks where small differences might still be considered substantially identical. What really helped me was creating a simple table showing: - Original contract: Underlying, Strike, Expiration, Sale Date - Replacement contract: Underlying, Strike, Expiration, Purchase Date - Days between transactions - Why they're NOT substantially identical This visual format made it much easier for Robinhood's tax team to understand why their automated system was wrong. I'd recommend anyone dealing with this issue to document it the same way - it really cuts through the confusion and gives them something concrete to work with. For what it's worth, after getting my corrected 1099, my additional deductible losses were about $8,400. Definitely worth the effort to fight these incorrect wash sale designations.

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Derek Olson

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This is exactly the kind of systematic approach I needed to see! Thank you for sharing that table format - it makes so much sense to document it visually rather than trying to explain it in paragraphs. I'm dealing with a similar situation where Robinhood flagged SPY options as wash sales even though they had different strikes and expirations. Your example with AAPL gives me confidence that these should definitely be challengeable. Quick follow-up question: when you submitted this to Robinhood, did you go through regular support channels or did you have to escalate to get someone who understood the nuance? And roughly how long did the whole process take from initial challenge to receiving the corrected 1099? Also, did your tax attorney charge a lot for helping with this? I'm trying to weigh whether it's worth getting professional help or if the documentation approach you described is enough to handle it myself.

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