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Just make sure you're reporting everything correctly! My brother tried to just "net" his gambling wins and losses a few years back (only reporting the difference) and got hit with an audit. The IRS requires you to report the FULL amount of the 1099-MISC as income, then deduct losses separately on Schedule A if you itemize. Don't make that mistake - the IRS computers will flag the mismatch between your reported income and what Underdog submitted on your 1099.
I went through almost exactly this situation two years ago - had a big 1099-MISC from FanDuel but overall losses for the year from other sites. Here's what I learned the hard way: You absolutely MUST report that full $10,400 as income even though you had net losses. Don't try to just report the "net" - the IRS computers will catch that immediately since Underdog already reported paying you $10,400. The good news is you can deduct your gambling losses, but only if you itemize deductions on Schedule A. You can deduct up to the amount of your winnings ($10,400 in your case), so theoretically you could zero out the tax liability from the gambling income. However, here's the catch that got me - you need to compare your total itemized deductions (including the gambling losses) to the standard deduction. If your standard deduction is higher, you're better off taking that and just paying tax on the $10,400. For the Bovada losses, keep every record you can find - transaction history, bank statements showing transfers, screenshots of your account summary. The IRS doesn't specifically exclude offshore sites, but documentation is absolutely critical. One more thing - don't forget about state taxes! Some states don't allow gambling loss deductions at all, so you might owe state tax on the full amount even if you can offset it federally.
This is really helpful, thanks for sharing your experience! I'm wondering about the documentation part - when you say "every record you can find" for the Bovada losses, how detailed did you need to get? Like did you need to document every single bet, or was it enough to show deposits/withdrawals and maybe monthly summaries? I'm trying to figure out how much work I'm looking at here to get my records together.
Great question! I went through this exact same confusion with my S-Corp last year. The short answer is NO - you don't need to spend all your money before year-end, and doing so could actually hurt you financially. As others have mentioned, S-Corps are pass-through entities, so you're taxed on profits regardless of where the cash sits. But here's what I wish someone had told me earlier: keeping cash in your business account is actually SMART for several reasons: 1. **Cash flow cushion** - Having reserves helps with irregular income months 2. **Business opportunities** - You can jump on good deals or investments when they come up 3. **Equipment replacement** - When something breaks, you have funds ready 4. **Quarterly tax payments** - Having business cash available for estimated taxes is super helpful The only thing you MUST do is pay yourself that reasonable salary throughout the year (sounds like you're on top of that). Beyond that, your cash management should be driven by business strategy, not tax avoidance. I used to stress about this every December and would buy random office supplies I didn't need. Now I keep healthy cash reserves and my business runs much smoother. Your $28k profit will be taxed the same whether it's in your business account or spent on unnecessary equipment!
This is really reassuring! I'm new to S-Corps and have been panicking about having leftover funds in December. Your point about quarterly tax payments is especially helpful - I hadn't thought about keeping business cash available for estimated taxes. That seems much smarter than scrambling to find personal funds every quarter or trying to spend down the business account on things I don't actually need. Quick question - do you have any recommendations for how much cash to keep as reserves? Is there a general rule of thumb for S-Corps, or does it just depend on your specific business situation?
Great question about cash reserves! There isn't a one-size-fits-all rule, but here are some guidelines I've learned: **General business rule:** 3-6 months of operating expenses is standard, but for S-Corps with irregular income, I'd lean toward 6+ months. **For your situation:** With $28k annual profit, keeping $10-15k in reserves seems reasonable. This covers: - 2-3 quarters of estimated taxes - Emergency equipment replacement - Slow income periods - Unexpected business opportunities **My approach:** I keep enough to cover my quarterly estimated taxes plus 3-4 months of typical business expenses (software subscriptions, phone, internet, etc.). For a side business like yours, that might be $8-12k depending on your expense structure. The key is finding the balance between having enough liquidity to run smoothly and not holding excessive cash that could be invested elsewhere. Since you have W-2 income providing stability, you might be comfortable with slightly lower reserves than someone whose S-Corp is their only income source. Start with 6 months of expenses and adjust based on how your business cash flow patterns develop over the year!
This is such a helpful discussion! I've been making the same mistake as Noah - worrying about having money left in my business account at year-end. Reading through all these responses really clarifies that the tax obligation exists regardless of where the cash sits. One thing I'd add for anyone in a similar situation: if you do decide to take distributions rather than leaving cash in the business, make sure you understand the timing implications. Distributions can be taken throughout the year, but they need to be properly documented and can't exceed your stock basis. Also, something that helped me was setting up automatic transfers for my quarterly estimated tax payments directly from the business account. Since I'm already being taxed on the S-Corp profits anyway, using business funds for those payments feels more organized than trying to remember to transfer money to personal accounts first. The peace of mind from having cash reserves in the business has been worth way more than any imaginary tax benefit from spending money I don't need to spend!
This is such a great point about using business funds directly for quarterly estimated tax payments! I never thought about that approach but it makes total sense - since the business profits are generating the tax liability anyway, why complicate things by moving money around unnecessarily? Your mention of stock basis is really important too. That's something I'm still trying to wrap my head around with my S-Corp. Do you have any simple way to track that, or do you just rely on your accountant to calculate it each year? I want to make sure I don't accidentally take distributions that exceed my basis and create additional tax complications. The automatic transfer setup sounds like a game-changer for staying organized. I've been manually moving money around each quarter and it's definitely more hassle than it needs to be.
I want to add another perspective as someone who went through this exact situation as an F1 student from South Korea. The consensus here is absolutely correct - Schedule D is the right form for your Robinhood trades. What really helped me understand this was learning about the "effectively connected income" test. The IRS considers three factors: (1) whether the income is from assets used in or held for use in conducting a trade or business in the US, (2) whether the business activities in the US were a material factor in producing the income, and (3) whether the income is derived from sources within the US. For F1 students actively trading stocks while physically present in the US, you typically meet criteria (2) and (3), making it ECI that goes on Schedule D. The good news about your India-US tax treaty question is that even though capital gains don't get special treaty rates, the ECI treatment means you avoid the 30% flat rate and get taxed like a US resident. I saved about $800 in taxes by having long-term capital gains taxed at 15% instead of my ordinary income rate of 22%. One practical tip: Since you mentioned you made $3,200 in gains, make sure to set aside money for taxes if you haven't already. Even with preferential rates, you'll likely owe something, and international students can't always make estimated payments as easily as US residents. The Schedule NEC advice from HR Block was definitely wrong - that form is for things like rental income from property in your home country or certain royalty payments, not US stock trading.
This is such a thorough breakdown of the ECI test - thank you! The three-factor analysis really helps clarify why stock trading while on F1 status qualifies as effectively connected income. I wish more tax preparers understood these nuances for international students. Your point about setting aside money for taxes is really important. I actually hadn't calculated what I might owe yet, so I should probably do that soon. Do you remember roughly what percentage of your gains you ended up paying in total taxes (federal + state if applicable)? Just trying to get a ballpark estimate for my own planning. Also, I'm curious about the estimated payments issue you mentioned. Are F1 students not able to make quarterly estimated payments like US residents? I thought if you expect to owe more than $1,000, you're supposed to make estimated payments regardless of visa status.
You can absolutely make estimated payments as an F1 student! I think there might be some confusion about this. F1 students who expect to owe $1,000 or more should make quarterly estimated payments just like anyone else filing in the US. The challenge is more practical than legal - many international students don't realize they need to make estimated payments, or they struggle with calculating the right amounts since our tax situations can be more complex with multiple income sources (campus job + trading + potentially treaty benefits). For my tax rate calculation: I ended up paying about 18% effective rate on my total capital gains between federal and state (I was in New York). My long-term gains were taxed at 15% federal + 8% NY state, while short-term gains were taxed at my ordinary income rate of 22% federal + 8% state. The blended rate worked out to around 18% since most of my gains were long-term. Your rate in California might be a bit different since CA has higher state tax rates, but you should still benefit significantly from the long-term capital gains treatment if most of your positions were held over a year. I'd recommend using Form 1040ES to calculate your estimated payments for next quarter if you expect similar trading activity this year.
As someone who works in tax compliance, I want to emphasize that everyone here giving advice about Schedule D being correct is absolutely right. The HR Block advisor who suggested Schedule NEC clearly doesn't understand the nuances of international student taxation. Here's a simple way to think about it: If you're physically in the US on F1 status and actively making investment decisions through a US broker like Robinhood, that activity creates "effectively connected income" that gets reported just like a US resident would report it - on Schedule D. Schedule NEC is specifically for income that's NOT effectively connected with US business activity. Think of it as income that would exist regardless of your physical presence in the US - like rental income from property you own back in India, or royalties from intellectual property. Regarding your tax rate concerns: Since your capital gains qualify as ECI, you'll pay graduated rates, not the flat 30%. Short-term gains (held less than 1 year) are taxed as ordinary income at your marginal rate, while long-term gains get the preferential rates (0%, 15%, or 20% depending on your total income). The India-US tax treaty doesn't provide special capital gains rates, but the ECI treatment is actually better for you anyway since it avoids the harsh 30% flat rate that applies to certain types of non-ECI investment income. Make sure to keep detailed records of all your transactions since you'll need to report each sale on Schedule D, even without a 1099-B from Robinhood.
This is such a clear and authoritative explanation - thank you! As someone new to this community, I really appreciate how thoroughly everyone has explained the Schedule D vs Schedule NEC distinction. I'm also an international student (F1 from Nigeria) and was getting conflicting advice from different sources about my cryptocurrency trading. Based on what you and others have explained here, it sounds like crypto trades made through US exchanges while I'm physically present in the US would also be treated as effectively connected income and reported on Schedule D, correct? The point about keeping detailed records is especially important - I've been tracking everything in a spreadsheet but wasn't sure if that level of detail was necessary. Sounds like it definitely is, especially without always receiving proper tax forms from exchanges. This thread has been incredibly educational for understanding how ECI works for international students with investment activities. Much more helpful than the generic advice I was getting elsewhere!
I'm dealing with the exact same situation - trading income with huge monthly variations and completely lost with these worksheets! Reading through everyone's responses has been incredibly helpful. @Oliver Cheng - your explanation about the Worksheet 2-8 error really cleared things up. It's honestly ridiculous that the IRS publications have these kinds of mistakes in them. So just to confirm: Worksheet 2-8 result goes on Line 11 of Worksheet 2-7, not where the instructions say? @Ashley Simian - for the AGI estimate issue, I'm wondering if there's a "safe" approach? Like, would it be better to overestimate or underestimate your expected income when you're really not sure? I'm worried about either underpaying and getting penalties or overpaying and tying up too much cash. The tools mentioned here (taxr.ai and Claimyr) sound promising, though I'm always cautious about new services. Has anyone compared the calculations from these tools to doing it manually to verify they're accurate? Also curious - when you're recalculating each quarter with updated info, do you adjust the remaining quarters' payments based on your new projections, or just calculate each quarter independently?
@Nina Chan - Great questions! Yes, Oliver is correct about the Worksheet 2-8 error - the result goes on Line 11 of Worksheet 2-7, not where the instructions indicate. I've seen this confusion trip up many traders. For the AGI estimation approach, I generally recommend being slightly conservative (estimating a bit higher rather than lower) for a few reasons: 1) It helps ensure you meet safe harbor requirements, 2) You'll get any overpayment back as a refund, and 3) Underpayment penalties are more painful than temporarily tying up cash. The key is "slightly" - don't go crazy with overestimation. Regarding the quarterly recalculations, you adjust going forward based on your updated projections. Each quarter, you look at your cumulative income through that period and recalculate what your total annual tax should be, then determine if you need to adjust future payments. It's not completely independent - you're always working with the year-to-date picture. One thing I'll add that others haven't mentioned: keep detailed records of your calculations and reasoning for each quarter. If you do get questioned by the IRS later, having documentation of your good faith effort to comply using the annualized method can be very helpful. The method exists specifically for people like traders with uneven income, so don't feel bad about using it properly.
@Oliver Fischer - Thanks for that detailed explanation! The conservative approach makes a lot of sense, especially about the safe harbor requirements. I hadn t'really thought about the documentation aspect either - that s'a great point about keeping records of the calculations and reasoning. One follow-up question: when you say slightly "conservative on" the AGI estimate, are we talking like 10-15% higher than your best guess, or something more modest? I m'trying to find that sweet spot between being safe and not over-withholding too much. Also, for the year-to-date recalculations each quarter - do you find it gets easier as the year progresses since you have more actual data to work with, or does it stay pretty complex throughout? I m'hoping by Q3 and Q4 the projections become more reliable since there s'less of the year left to estimate.
Miguel Herrera
did you by chance do a split refund where part went to a bank account and part to a prepaid card? that messed up my refund timing last year
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Emma Johnson
ā¢Nope, just straight to my checking account. Same one I've used for years.
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Ben Cooper
I work in banking and see this all the time during tax season. The "pending" status often appears when the IRS has already sent the ACH file to your bank but their website hasn't updated yet. Banks typically process these overnight or in batches throughout the day. A few things to check: - Log into your online banking and look for any pending transactions (sometimes they show up there first) - Call your bank's customer service - they can often see incoming ACH transfers before they post - The IRS processes refunds in cycles, so yours might hit tonight or tomorrow morning I'd say there's about an 80% chance you'll still get it today or tomorrow despite the status change. The timing between IRS systems and actual bank deposits isn't always synchronized. Try not to stress too much - delays like this are super common and usually resolve within 24-48 hours.
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