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Dumb question maybe but what happens at the end of the year with wash sales? If I have disallowed losses from December, do they just disappear?
This is actually a really important question! Wash sales that happen at year-end need special attention. If you sell at a loss in December and then buy back in January (within 30 days), that creates a wash sale that spans tax years. The loss doesn't disappear, but it gets added to the cost basis of your new shares purchased in January - which means you can't claim the loss on this year's taxes. You won't realize that benefit until you eventually sell those January shares (potentially next tax year or beyond). This is why some traders do "year-end tax planning" and avoid rebuying securities they've sold at a loss in December until after the 30-day window has passed.
Great explanation from everyone here! As someone who got burned by wash sales in my first year of active trading, I want to emphasize how important it is to track these across ALL your accounts. I had Fidelity, E*TRADE, and a small Robinhood account, and each platform only reported wash sales within their own system. What really helped me was setting up a simple spreadsheet to track any stock I sold at a loss, with a 30-day "no buy" reminder. Sounds tedious but it saved me from creating unnecessary wash sales, especially during volatile periods when I wanted to jump back into positions quickly. Also worth noting - if you have a spouse who trades, their transactions count toward YOUR wash sale calculations too! Found that out the hard way when my wife bought Tesla shares two weeks after I sold mine at a loss. The IRS considers all accounts under the same tax filing, so coordinate with your partner if applicable. For anyone doing tax-loss harvesting near year-end, be extra careful about the calendar. That 30-day window can easily cross into the new tax year and mess up your planning.
Just wanted to add another perspective on the F1 visa work authorization issue. I run a digital marketing agency and went through this exact situation last year with a talented MBA student from Brazil. The process ended up being more straightforward than I initially feared, but timing was everything. She applied for CPT through her university since our marketing work directly related to her MBA coursework. The university's international office was incredibly helpful - they walked her through the entire application process and had her authorized within about 2 weeks. One thing I learned is that CPT has some advantages over OPT in this situation. CPT can be used while she's still in school and doesn't count against her OPT time (which she might want to save for after graduation). The downside is that CPT requires the work to be directly related to her field of study, so you'd need to make sure the marketing role aligns with her MBA program. For the tax side, I ended up working with a CPA who specializes in international contractors. Worth every penny - they handled all the withholding requirements and made sure we filed the right forms. The 30% withholding rate was reduced to 15% because of the US-Brazil tax treaty, but we needed Form 8233 to claim that benefit. My advice: get her to her international student office ASAP, and don't be afraid to invest in professional help for the tax compliance piece. The potential penalties for getting this wrong far outweigh the cost of doing it right.
This is really helpful to hear about a successful case! The CPT route sounds like it could be perfect for OP's situation since it's marketing work for an MBA student. I'm curious - when you worked with the CPA who specializes in international contractors, how did you find them? Did you just search for "international tax CPA" or is there a specific certification or specialty area to look for? I'm starting to realize that trying to navigate all these treaty provisions and withholding requirements on my own might be asking for trouble.
As someone who's navigated similar waters, I can't stress enough how important it is to get this right from the start. The good news is that if she's pursuing an MBA and this is marketing work, CPT could be a great option since it's directly related to her field of study. Here's what I'd recommend as immediate next steps: 1) Have her schedule an appointment with her university's international student services office this week - they'll know exactly what authorization options are available and can guide her through the application process. 2) Don't start any work relationship until you have her work authorization documents in hand, even if it's just a few hours here and there. 3) Once she gets authorization, connect with a CPA who has experience with international contractors to handle the tax compliance piece properly. The whole process took about 3-4 weeks for a similar situation I dealt with last year, and having proper authorization from the start saved us from potential compliance nightmares later. Yes, there's some upfront complexity with the tax withholding and reporting requirements, but it's definitely manageable with the right professional guidance. The investment in doing this correctly will pay off in peace of mind and avoiding any future issues with immigration or tax authorities.
This is such valuable advice! As someone new to hiring international talent, I'm realizing there are so many moving pieces I hadn't considered. The 3-4 week timeline you mentioned is really helpful for planning purposes. I'm curious - during that waiting period while the CPT application was processing, were you able to do any preliminary work like onboarding, training materials review, or project planning? Or is it strictly no work of any kind until the authorization is officially approved? I want to make sure I understand exactly where the line is drawn to avoid any accidental violations. Also, when you mention connecting with a CPA experienced in international contractors, did you find that most general CPAs can handle this, or do you really need someone with specific expertise in this area? I'm trying to figure out if I need to expand my search beyond my current accountant.
Based on the excellent discussion here, I'd recommend a phased approach that balances tax efficiency with your diversification goals. Since your son is only 12, you have time to be strategic. First, request detailed tax lot information from your broker showing the purchase dates and cost basis for each gift. Look for any positions that are at a loss or have minimal gains - these should be your first candidates for selling and reinvesting in your S&P 500 fund. For the remaining positions, consider selling just enough each year to stay under the $2,500 kiddie tax threshold (around $1,250 in actual gains after the standard deduction). This gradual approach will take several years but avoids the large tax hit while steadily reducing concentration risk. However, if college is definitely in your son's future, there's merit to accelerating this timeline. Completing the diversification by his sophomore year of high school could significantly improve financial aid eligibility, as UTMA assets are assessed at 20% versus 5.64% for parent assets like 529 plans. One hybrid strategy: sell positions with the highest cost basis first (lowest taxable gains), reinvest in index funds, and keep 1-2 of the best performing individual stocks with the lowest basis. This gives you diversification while maintaining some upside exposure. Also consider discussing future gifting strategy with your brother-in-law - cash gifts instead of appreciated stock would avoid this complexity going forward.
This is such a comprehensive strategy - thank you for laying it all out so clearly! As someone new to managing UTMA accounts, I really appreciate how you've broken down the different approaches based on timeline and priorities. The idea of requesting detailed tax lot information makes total sense, but I'm wondering - do most brokerages provide this automatically, or is this something I need to specifically request? Also, when you mention keeping 1-2 of the best performing stocks with the lowest basis, how do you balance that against the concentration risk? Is there a rule of thumb for what percentage of the portfolio should remain in individual stocks versus moving to diversified funds? One other question about the college timeline strategy - if we do accelerate the selling to improve FAFSA eligibility, would it make sense to reinvest the proceeds in a 529 plan instead of keeping everything in the UTMA? I know there are tax implications for moving money between account types, but the better financial aid treatment might be worth considering.
Most brokerages will provide detailed tax lot information if you request it, though the format varies. You can usually find this in your online account under "tax documents" or "cost basis reporting," or call and ask for a "detailed position report" that shows each lot's purchase date, shares, and cost basis. For concentration risk, a common rule of thumb is to limit individual stock positions to 5-10% of the total portfolio each. If your son's account has grown to where individual positions exceed this, that's when diversification becomes more critical than tax optimization. Regarding the 529 strategy - you cannot directly transfer securities from a UTMA to a 529. You'd need to sell the stocks (triggering capital gains), then make cash contributions to a 529 plan. While the 529 would get better financial aid treatment, you'd lose the "step-up in basis" that occurs when your son inherits the UTMA at majority age. A middle-ground approach might be to gradually sell portions of the UTMA over several years, paying the kiddie tax, then contributing the after-tax proceeds to a 529. This spreads the tax impact while improving the financial aid profile. You could also consider keeping some funds in the UTMA for non-education expenses since 529s have penalties for non-qualified withdrawals. The key is modeling different scenarios with actual numbers to see which approach saves the most money long-term considering taxes, financial aid impact, and your family's specific college/career plans.
This is incredibly helpful guidance, thank you! I'm new to managing these types of accounts and the complexity of coordinating tax implications with college planning is pretty overwhelming. One follow-up question - when you mention the "step-up in basis" that occurs when my son inherits the UTMA at majority age, can you explain how that works? I thought UTMA accounts already belonged to the child, so I'm not sure I understand what changes at the age of majority from a tax perspective. Does this mean if we hold the appreciated stocks until he's 18-21 (depending on our state), he could potentially sell them with a reset cost basis? Also, regarding the modeling of different scenarios - are there any online calculators or tools that can help compare the long-term financial impact of these different strategies? It sounds like we need to weigh immediate taxes, future financial aid eligibility, and potential college costs, which seems like a lot of variables to manage manually.
Does anyone know if the IRS ever provides this breakdown when they send your refund? Like some kind of statement that says "You received $X for Child Tax Credit, $Y for Earned Income Credit" etc.? In Canada, their tax agency sends a detailed explanation with the refund payment, wondering if the IRS does something similar.
No, the IRS doesn't provide that level of breakdown with your refund deposit or check. They'll send you a notice confirming your refund amount was processed, but it doesn't break down which credits contributed what amount. The only way to get that detailed info is either through your tax software analysis, manually calculating it yourself by looking at your forms, or contacting the IRS directly and asking an agent to walk through it with you.
For anyone still looking for a simple solution within TurboTax itself, there's actually a really useful feature called "View Your Tax Summary" that breaks down your refund components. After you complete your return, go to the final review screen and look for a link that says something like "Why is my refund this amount?" or "View detailed summary." This will show you a breakdown that includes: - Total tax before credits - How much each credit reduced your tax - Your total withholdings and estimated payments - The final refund calculation It's not as detailed as some of the third-party tools mentioned here, but it gives you a good overview of the major contributors to your refund without needing to upload your documents anywhere else. I found this really helpful for understanding that my refund wasn't just from overwithholding - a big chunk actually came from the credits I qualified for!
Amara Okafor
Make sure you understand the rules for "support" with college students! My ex and I got audited because we misunderstood this. For kids in college, their scholarships, grants and student loans in THEIR name count toward THEIR contribution to their own support. If your son gets enough scholarships/loans, he might actually be providing more than half of his own support (room, board, etc), which means NEITHER of you could claim him!
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Giovanni Colombo
•That's not entirely accurate. Scholarships used for tuition and required fees don't count as support provided by either parent or the student. Only scholarships for room and board count toward support calculations.
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Lydia Santiago
Just wanted to add something important about timing - make sure you coordinate WHEN each parent files their taxes if you're alternating years claiming your son. The IRS computer system will flag it if both parents try to claim the same dependent on returns filed around the same time, even if it's for different tax years. Also, keep excellent records of your agreement and the Form 8332 filings. I've seen situations where the IRS questions these arrangements years later, especially if there are any changes to custody or support arrangements. Having clear documentation from the start saves a lot of headaches down the road. One more tip - consider having a conversation with your son about this plan. As he gets older and starts filing his own returns, he needs to understand he can't claim himself as a dependent in years when one of you is claiming him. Sounds obvious, but college kids make this mistake more often than you'd think!
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