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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.
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.
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.
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.
Derek Olson
ā¢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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This is such a comprehensive discussion! As someone new to this community but facing very similar decisions with my two adult kids, I'm finding all these perspectives incredibly valuable. One aspect I haven't seen fully explored is the psychological impact on the kids themselves. My concern isn't just about encouraging good financial habits, but also about how receiving significant gifts might affect their self-reliance and confidence in their own earning ability. Has anyone dealt with kids who became anxious about their own financial capabilities once they knew substantial family money was available? I worry that even well-intentioned gifts with conditions might create a dependency mindset or make them second-guess major financial decisions, wondering if they should wait for family assistance rather than solving problems themselves. I'm particularly drawn to the milestone matching approach mentioned by several people here - it seems like it could encourage good behavior while still requiring them to take the initiative. But I'm curious whether anyone has found their kids becoming too focused on meeting "gift criteria" rather than making decisions based on their own goals and values. The trust vs. direct gift debate is fascinating, but I keep coming back to whether we're solving the right problem. Maybe the issue isn't how to control the money, but how to raise kids who make good decisions regardless of whether family money is involved?
Ava Johnson
ā¢You've raised such an important point about the psychological impacts that often gets overlooked in these planning discussions! As someone who's been part of this community for a while but new to this particular conversation, I think you're absolutely right to focus on the mindset effects. I've seen families where well-intentioned financial support actually undermined the kids' confidence in their own decision-making abilities. One thing that might help is involving your kids in the planning process from the beginning - explaining your goals and asking for their input on what kind of support would feel empowering rather than controlling. The milestone approach seems promising specifically because it requires them to take initiative first, but I'd suggest making sure the milestones align with goals they've already expressed rather than goals you think they should have. That way you're supporting their vision rather than potentially redirecting it. Maybe start with a family conversation about financial values and long-term goals before implementing any formal gifting strategy? Understanding what success and independence mean to each of your kids individually could help you design support that builds their confidence rather than creating dependency concerns.
Carmen Ruiz
This is such a valuable discussion! I'm new to the community but have been wrestling with similar decisions for my two adult children. Reading through everyone's experiences has been incredibly helpful. One thing that really resonates with me is the balance between providing support and maintaining their independence. I've been leaning toward the annual gift exclusion approach combined with some of the milestone matching strategies mentioned here, but I'm also concerned about the family dynamics aspects that several people have raised. The point about involving kids in the planning process seems crucial. I think I'd been approaching this too much from a "we know what's best" perspective rather than understanding what kind of support would actually be meaningful to them. The psychological impact concerns raised by KingKongZilla really hit home - I don't want to inadvertently undermine their confidence or create anxiety about their own financial capabilities. I'm particularly interested in the hybrid loan-to-gift conversion approach mentioned by a few people. It seems like it could provide the structure I'm looking for while still requiring them to take initiative and demonstrate responsibility first. Has anyone found that starting these conversations with adult children gets easier over time? I'm honestly a bit nervous about bringing up the topic since I don't want them to feel like I'm questioning their judgment or trying to control their choices. Any advice on how to frame these initial discussions would be really appreciated!
Welcome to the community, Carmen! Your nervousness about starting these conversations is completely understandable - I think most of us felt the same way initially. What helped me was framing the initial discussion around our own estate planning process rather than focusing on gifts to them specifically. I started by saying something like "We're updating our estate plan and want to make sure we're thinking about this thoughtfully. We'd love to understand your perspectives on financial goals and what kind of support, if any, might be helpful as you build your careers." This made it feel more collaborative and less like we were making assumptions about their needs. The loan-to-gift conversion approach you mentioned has worked really well for us. The key is making sure the "conversion milestones" are things they genuinely want to achieve anyway, not hoops we're making them jump through. For example, if they're already planning to buy a house, offering to convert a down payment loan to a gift after they've successfully managed homeownership for a year feels supportive rather than controlling. One thing that surprised me was how much my kids appreciated the transparency about our financial planning goals. They actually had great insights about what would feel empowering versus what might create pressure. Starting with open-ended questions about their own financial priorities made the whole conversation much more natural.
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I'm glad to see everyone sharing such helpful advice about IRS rounding policies! As a tax professional, I can confirm that the guidance shared here is spot-on. The IRS Publication 17 specifically states that you can round off cents to whole dollars on your return and schedules, and this applies across virtually all tax forms. What I find particularly valuable about this thread is the discussion around managing tax anxiety, especially for those dealing with OCD. The "checking budget" approach mentioned by Miguel is something I often recommend to clients who get stuck in verification loops. Setting reasonable limits on review time actually leads to better outcomes because it prevents the kind of over-analysis that can introduce errors. For anyone still worried about precision: in my 15+ years of practice, I've never seen the IRS question returns based on consistent dollar rounding. They're far more concerned with accuracy of income reporting and legitimate deduction claims than they are with cents-level precision. Your good faith effort to be accurate is what matters most.
Thank you so much for the professional perspective! It's really reassuring to hear from someone with 15+ years of experience that the IRS has never questioned returns based on consistent dollar rounding. As someone new to this community and dealing with my first solo tax filing, I was getting really anxious about every small detail. The combination of practical advice about rounding rules and the mental health strategies for managing tax anxiety has been incredibly helpful. I feel much more confident now about moving forward with my return using the standard rounding approach. This community is amazing for supporting people through these stressful processes!
Kaitlyn Otto
I really appreciate everyone's thorough responses here! As someone who also deals with tax anxiety (though not OCD), this thread has been incredibly educational. What struck me most is how consistent everyone's advice is - from tax professionals to people who've called the IRS directly - that rounding to the nearest dollar is not just acceptable but actually preferred. The practical tips about setting checking limits and creating written rounding rules are gold. It's so easy to get caught in perfectionist spirals during tax season, but hearing from actual professionals that the IRS systems are designed to handle these minor variations gives me a lot of peace of mind. For anyone else reading this who might be struggling with similar concerns: it sounds like the key takeaway is consistency and good faith effort matter way more than perfect precision. The IRS is looking for significant discrepancies, not penny-level differences from people genuinely trying to file accurately. Thanks to everyone who shared their experiences and expertise!
As a newcomer to this community, I just want to echo how valuable this entire discussion has been! I stumbled across this thread while researching the exact same rounding question for my own tax return, and the depth of knowledge shared here is incredible. What really stands out to me is how this conversation evolved from a technical question about IRS policies into such a comprehensive resource covering both the practical aspects (official rounding rules, which forms they apply to) and the emotional/mental health side of tax preparation. The advice about managing OCD-related checking behaviors and general tax anxiety is something I haven't seen addressed so thoughtfully in other tax forums. It's reassuring as someone new to filing independently to see such a supportive community where people share real experiences, professional insights, and practical tools. The consensus from multiple perspectives - tax professionals, people who've spoken directly with IRS agents, and those with personal experience - all pointing to the same guidance gives me confidence that I'm getting accurate information. Thank you all for creating such a helpful resource!
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Diego Rojas
Navy Federal member here! I've been banking with them for about 4 years and can confirm they're really solid for tax refunds. Since your DDD is 3/22 (Saturday), you'll most likely see the deposit hit on Friday 3/21 or even Thursday 3/20. Navy Fed doesn't play games with holding tax refunds like some of the bigger banks do. A couple things that might help ease your mind: ā¢ Navy Fed typically processes overnight between 12am-6am EST ā¢ Their mobile app notifications are instant when deposits hit ā¢ They've never held my tax refunds past the processing date ā¢ Even if there's a delay, it's usually only 1 business day max Since you mentioned this is for your post-graduation move, you might want to give yourself a small buffer just in case. But honestly, based on my experience and what I've seen from other Navy Fed members, you should have your money by Friday at the latest. The prepaid card thing really isn't worth it when you have a reliable bank like Navy Fed - those fees add up quick and you're only saving maybe 2-3 days at most. Congrats on graduation btw! š
Thanks Diego! This is really reassuring to hear from someone with actual Navy Fed experience. I was getting a bit stressed about the timing since I need to coordinate with my landlord, but it sounds like Friday 3/21 is a pretty safe bet. I definitely don't want to deal with prepaid card fees when Navy Fed seems so reliable. Really appreciate you taking the time to break down their processing schedule - the overnight timeframe is super helpful to know. And thanks for the graduation congrats! š
Lucas Adams
I've been with Navy Federal for about 6 years and they've been consistently reliable with tax refunds! Since your DDD is 3/22 (Saturday), you'll almost certainly see the deposit by Friday 3/21, possibly even Thursday 3/20. Navy Fed processes ACH deposits as soon as they receive them from the Federal Reserve rather than holding until the official date. A few things that might help: ā¢ Download the Navy Fed app if you haven't already and enable push notifications ā¢ Deposits typically process overnight between 2-6am EST ā¢ Since it's your first tax season with them, double-check your account/routing numbers one more time ā¢ They don't charge any fees for receiving tax refunds (unlike those prepaid cards) For your moving situation, I'd plan on having the funds available by Friday 3/21 but maybe don't schedule anything critical for Thursday just to be safe. Navy Fed has never let me down with tax refunds, and $3,200 should definitely cover your post-graduation move! Good luck and congrats on finishing school! š
Kayla Jacobson
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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William Rivera
ā¢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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Katherine Ziminski
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
ā¢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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