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Ask the community...

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Luis Johnson

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I shorted Apple last year and paid out dividends. The way I handled it (confirmed by my CPA) was: 1. Report the full dividend amount from my 1099-DIV on Schedule B 2. The dividend I paid on my short sale gets added to the cost basis of the short position 3. When I closed my short position, the adjusted basis meant I had a smaller gain So you're not really "deducting" it directly from your dividend income. You're adjusting the cost basis of the short sale transaction, which affects your capital gain/loss instead.

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Ellie Kim

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So to be clear, if I'm understanding right: - You report the full $125 dividend income - You add the $27 to the cost basis of your short position - When you close the position, your gain is $27 less than it would have been otherwise So the tax benefit comes when you close the position, not when you report dividends?

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Yuki Tanaka

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Exactly right! You've got it. The tax benefit happens when you close the short position, not when you report the dividends. So in your example: - Report full $125 on Schedule B - Your short position cost basis increases by $27 - When you close the short, your capital gain is reduced by $27 (or loss increased by $27) This way you're still getting the tax benefit of that $27, just through the capital gains/loss calculation instead of directly reducing dividend income. The IRS wants to see the transactions reported separately since they're technically different types of income/expenses.

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This is a great question that catches a lot of people off guard! I went through the same confusion when I first started shorting stocks. The key thing to understand is that you cannot simply net the $27 against your $125 in dividend income on your tax return. Here's what you need to do: 1. **Report the full $125 on Schedule B** - This matches what your broker reported to the IRS on your 1099-DIV 2. **Add the $27 to your short position's cost basis** - The dividend payments you made while shorting increase the cost basis of that short sale 3. **The tax benefit comes when you close the short position** - Your capital gain will be $27 less (or capital loss $27 more) when you eventually close the position Think of it this way: the IRS wants to see dividend income and capital gains/losses reported in their proper categories. You're not losing the tax benefit of that $27 - you're just getting it through the capital gains calculation instead of directly reducing dividend income. Make sure to keep good records of these payments so you can properly adjust your cost basis when you close the short positions!

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Thank you so much for this clear explanation! As someone new to short selling, this helps me understand the bigger picture. I have a follow-up question though - what happens if I'm still holding the short position at year end? Do I still need to adjust the cost basis even if I haven't closed the position yet, or does that adjustment only matter when I actually close it out? Also, should I be keeping track of these dividend payments separately from what my broker reports, or will they typically include this information in my year-end statements?

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My nightmare experience with Sprintax - avoid for non-resident tax filing

I need to warn fellow non-residents about my terrible experience with Sprintax this tax season. I filed my taxes late (had some personal stuff going on) and decided to use Sprintax since I'm a non-resident alien. The whole experience was a disaster from start to finish. After completing all the forms and paying the fees, I was shocked to discover it would take 3-5 days to prepare my forms. Every other tax software I've used (like Glacier Tax Prep) generates forms automatically! This meant my forms might not be ready before the deadline, which was super stressful. Here's what made me furious - there were ZERO warnings about this processing time before I paid. None. If I had known, I never would have chosen Sprintax. When I contacted customer service about this issue, they refused to give me a refund (ridiculous!) but promised my forms would be ready before the deadline and that I'd get an email notification. I checked back on Saturday and saw my federal return was finished, but never got any email about it. Then today I logged in to check on my state return, and it still wasn't completed! When I tried chatting with customer service again, the agent had the nerve to claim I had "agreed that forms might not be ready on time" during application - which is a total lie. Then they just closed the chat on me! I tried again with another agent and asked to file a complaint. They dismissed me repeatedly and claimed their system showed me warning pop-ups - another complete lie. I read EVERYTHING carefully before clicking and paying. The software is bad enough, but their customer service is truly atrocious. I'm out $75 and still don't have my complete tax forms. Please save yourselves the headache and avoid Sprintax completely. I'm never using them again.

Carmen Ortiz

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I'm so sorry you went through this with Sprintax - what a nightmare! As someone who's dealt with non-resident tax issues for years, I can tell you that their lack of transparency about processing times is unacceptable, especially so close to deadlines. For anyone reading this who needs to file as a non-resident in the future, here are some tips to avoid this situation: 1. File early - even if you're using software, give yourself at least 2-3 weeks before the deadline 2. Always read the fine print about processing times before paying 3. Check if your employer/university has partnerships with tax prep services first 4. Keep screenshots of any promises made during the signup process in case you need to dispute charges The fact that they closed chat on you and lied about warning pop-ups is completely unprofessional. Document everything and definitely consider the chargeback route that others have mentioned - you have a strong case since they didn't deliver the service as promised. Hope you can get this resolved and your taxes filed properly!

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Leila Haddad

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This is exactly why I always warn people about Sprintax! I had a similar experience two years ago where they took my money and then informed me AFTER payment that there would be a multi-day processing delay. What really got me was their customer service - they act like you're the problem for not magically knowing about their hidden delays. I ended up having to file an extension because of their incompetence, which was stressful and embarrassing. Since then, I've used FreeTaxUSA for my non-resident filing and it's been much better - forms generate immediately and their customer service actually responds helpfully when you need them. For your current situation, definitely document everything (screenshots, chat logs, emails) and file a chargeback with your credit card company. Many people have had success with this approach since Sprintax fails to deliver services as advertised. You shouldn't have to eat that $75 for their terrible service.

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I'm new to filing as a non-resident and this thread is honestly terrifying me about using any tax software! Can I ask - does FreeTaxUSA actually handle all the non-resident specific forms like 1040NR and treaty benefits correctly? I'm on F-1 status with some scholarship income and I'm worried about messing something up. The immediate form generation sounds amazing compared to what everyone's describing with Sprintax. Also, for the chargeback approach - do you need to wait a certain amount of time before disputing, or can you file it right away when they don't deliver as promised?

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Miguel Castro

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Don't be terrified! Yes, FreeTaxUSA does handle 1040NR and most common non-resident situations well, including F-1 scholarship income. It correctly separates taxable vs non-taxable scholarship portions and has good guidance for treaty benefits. For your F-1 situation specifically: make sure you have your 1042-S forms from your university, and double-check that any fellowship/scholarship income is reported correctly. The software will walk you through it, but it's always worth reviewing the final forms before submitting. Regarding chargebacks - you can typically file immediately once it's clear the service won't be delivered as promised. Most credit card companies give you 60-120 days from the charge date, but the sooner you file, the stronger your case. Just make sure to document everything - screenshots of their promises, chat logs showing poor service, etc. You've got this! Filing as a non-resident seems scary but it's totally manageable with the right tools.

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Just wanted to add one more important detail that I learned the hard way - make sure you understand what qualifies as a "first-time homebuyer" for IRS purposes. It's not just about never owning a home before. You (and your spouse if married) must not have owned a principal residence during the 2-year period ending on the date you acquire your new home. So if you owned a home 18 months ago, you wouldn't qualify yet. Also, the $10,000 is a lifetime limit per person, so if you're married, you and your spouse can each use up to $10,000 from your respective IRAs for a total of $20,000. But if you're single, you're stuck with the $10,000 limit across all your accounts combined. Make sure to keep detailed records of everything - when you withdrew the money, what you used it for, and proof that you meet the first-time homebuyer requirements. The IRS can be pretty strict about documentation if they audit you later.

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This is really helpful clarification! I had no idea about the 2-year rule - I was thinking "first-time" just meant never owned before. So if someone sold their house 3 years ago, they'd still qualify as a "first-time" buyer for this exemption? That's actually pretty generous of the IRS. The married couples getting $20K total ($10K each) is interesting too. Does that mean each spouse needs their own IRA to get the full benefit, or can one spouse withdraw $20K from their single account if the other spouse doesn't have retirement savings? Thanks for emphasizing the documentation part - I've heard IRS audits on retirement withdrawals can be brutal if you don't have your paperwork in order.

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Important clarification about married couples and the $20K limit! Each spouse can only withdraw up to $10,000 from their own IRA accounts - you can't have one spouse withdraw $20K from their single account just because they're married. The benefit only applies if both spouses have their own retirement accounts. So if you're married and only one of you has an IRA, you're still limited to $10,000 total for the first-time homebuyer exemption. Both spouses need to have their own IRA accounts to get the full $20,000 benefit ($10K from each person's accounts). Also worth noting that the "qualified acquisition costs" this money can be used for include more than just the down payment - you can use it for closing costs, financing fees, and other expenses related to buying or building the home. Just make sure to keep receipts for everything since the IRS may ask for documentation later.

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Thanks for that clarification about married couples! That makes total sense - each person can only access their own retirement accounts. I was getting my hopes up thinking we could double-dip from one account. The expanded definition of "qualified acquisition costs" is really useful to know. I was only thinking about the down payment, but knowing I can use it for closing costs and financing fees gives me more flexibility in planning my withdrawal strategy. Those closing costs can really add up - sometimes 2-3% of the home price. One follow-up question: do these qualified costs have to be paid directly from the IRA withdrawal, or can I withdraw the money, deposit it in my regular account, and then use those funds mixed with other money for the purchase? I'm wondering about the paper trail requirements for an audit.

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Rajiv Kumar

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Pro tip: the cycle code on your transcript can tell you your update schedule. Look at the last 2 digits - 05 means Thursday updates, 03 means Wednesday, etc. But honestly just use taxr.ai and save yourself the headache of trying to decode all this stuff

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James Johnson

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whats a cycle code? where do i find that?

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Rajiv Kumar

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It's in your transcript but trust me you dont wanna go down that rabbit hole. Just use the AI tool, its way easier

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Amara Okafor

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Been there! The obsessive checking is real šŸ˜… From my experience, WMR typically updates overnight between 3-6am EST like others mentioned, but transcripts are more unpredictable. I've seen updates on random days throughout the week. The cycle code thing is helpful if you can figure it out, but honestly the IRS system has been pretty inconsistent lately. My advice? Pick one time per day to check (maybe early morning) and try to resist the urge to refresh constantly - it'll just drive you crazy and won't make your refund come any faster!

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Laura Lopez

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This is such good advice! I definitely fell into the obsessive checking trap too - was literally refreshing every few hours thinking it would somehow make a difference šŸ˜‚ You're totally right about picking one time per day, wish I had done that from the start instead of driving myself nuts!

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StarSurfer

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This is such a helpful thread! I'm dealing with a similar situation with my first rental property purchase. One thing I learned from my research is that even though MACRS assumes zero salvage value for the depreciation calculation, you should still keep good records of any major improvements you make to the property over the years. The reason is that improvements have their own depreciation schedules - so if you put on a new roof, install new HVAC, or do major renovations, those get depreciated separately from the original building. This can actually increase your total annual depreciation deduction. Also, I found IRS Publication 946 (How to Depreciate Property) really helpful for understanding all the nuances. It's dense reading but covers scenarios like partial business use, mixed-use properties, and how to handle improvements vs. repairs. Definitely worth checking out if you want to understand the full picture beyond just the basic residential rental depreciation.

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Zoe Gonzalez

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This is exactly the kind of detailed info I was looking for! I had no idea about the separate depreciation schedules for improvements. Does this mean if I replace the flooring in my rental, I should track that separately from the building depreciation? And how do you determine what counts as an "improvement" versus just regular maintenance and repairs?

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Great question! Yes, you should definitely track flooring replacement separately. The key distinction is that improvements add value, extend the useful life, or adapt the property for a new use, while repairs just maintain the current condition. Replacing flooring would typically be considered an improvement and gets its own depreciation schedule (usually 5-7 years depending on the type). Regular maintenance like fixing a leaky faucet or touching up paint would be a current-year deductible repair. Some examples: New flooring = improvement (depreciate over 5-7 years). Fixing a broken tile = repair (deduct immediately). New HVAC system = improvement (depreciate). Replacing a broken HVAC part = repair. The IRS has gotten stricter about this in recent years, so good documentation is crucial. I keep a separate spreadsheet tracking all improvements with receipts, dates, and depreciation schedules. It's saved me during an audit because I could show exactly how I categorized everything.

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Kyle Wallace

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Great discussion everyone! As someone who just went through this process with my first rental property, I want to add a few practical tips that might help others avoid the mistakes I made initially. First, when separating land and building values, don't just rely on the property tax assessment - it can sometimes be way off. I found it helpful to get a professional appraisal that specifically breaks down land vs. building value, especially since this affects your depreciation for the entire 27.5-year period. Second, keep meticulous records from day one. I created a simple folder system: one for the original purchase documents, one for improvements, and one for repairs/maintenance. This makes tax prep so much easier and you'll be prepared if you ever get audited. Finally, don't forget about the "mid-month convention" for real estate depreciation - you only get half a month's depreciation in the month you place the property in service, regardless of when in the month you actually start renting it out. This caught me off guard in my first year. The zero salvage value rule for MACRS really does simplify things compared to other types of assets. Just focus on getting that land/building split right and you'll be in good shape!

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This is incredibly helpful advice, especially about the mid-month convention - I had no idea about that rule! I'm just starting to look into purchasing my first rental property and this thread has been a goldmine of information. Quick question: when you mention getting a professional appraisal for the land/building split, roughly how much does that typically cost? I'm trying to budget for all the upfront expenses and want to make sure I'm not missing anything important. Also, do you recommend getting this appraisal done before closing or can it be done after you've already purchased the property?

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