This is so true! I freaked out last year thinking my payment didn't go through, even called Marcus support. They explained that tax payments process differently than regular transfers. As long as you got the confirmation email from TurboTax, you should be good.

This is super helpful! I was just checking my Marcus account and didn't see anything pending yet, so was starting to worry. I'll give it a day before I start panicking. Thanks for sharing that!

Options trading in a UTMA account? Is that even allowed? Seems pretty risky for an account that's supposed to be for a minor. I thought most custodians limited UTMA accounts to stocks, mutual funds, ETFs and maybe bonds. Wouldn't the custodian need special approval for options trading?

You're absolutely right to question this. Most brokerages don't allow options trading in UTMA accounts, and even if they did, it would likely require special approval and involve significant risks that may not be appropriate for a minor's account. As a custodian, you have a fiduciary duty to act in the child's best interest, and speculative strategies like options could be seen as violating that duty. The suggestion about future gifting strategy is much more practical though. Having the brother-in-law gift cash instead of appreciated securities would definitely avoid this tax complexity going forward. You could then invest in diversified index funds from day one without having to worry about concentrated positions or capital gains taxes down the road.

I need to clarify something important - I made an error in my previous response about the "step-up in basis." UTMA accounts don't receive a step-up in basis when the child reaches the age of majority. The step-up in basis only occurs at death for inherited assets, not when UTMA control transfers to the child. What actually happens at the age of majority is that your son gains full control of the account, but the cost basis of the securities remains the same as when they were originally gifted. So if your brother-in-law gifted stocks with a $10,000 basis that are now worth $28,000, your son will still have that $10,000 basis when he takes control at 18-21. This actually strengthens the case for strategic tax planning now rather than waiting. The gains will be taxable whenever the stocks are sold, whether that's now (under kiddie tax rules) or later when your son has control. For modeling tools, many financial advisors use software like eMoney or MoneyGuidePro, but for DIY planning, you might consider tools like the College Board's financial aid estimator to model FAFSA impact, combined with basic tax calculators. Some of the tax planning tools mentioned earlier in this thread (like taxr.ai) might also help model different selling scenarios. The key variables to compare are: immediate tax cost, future financial aid impact, and investment growth potential of the diversified portfolio versus keeping the concentrated positions.

I need to clarify something important - there actually isn't a "step-up in basis" for UTMA accounts when the child reaches majority age. I think there might be some confusion with inheritance rules here. UTMA assets already legally belong to the child from the moment they're gifted, and the cost basis remains whatever it was when originally gifted (the donor's basis, not fair market value at time of gift). When your son reaches the age of majority, he simply gains full control of the account - the tax basis doesn't reset. The step-up in basis you might be thinking of applies to inherited assets after someone dies, where the beneficiary receives assets with a cost basis equal to their fair market value at the date of death. That's completely different from UTMA transfers at majority age. For modeling tools, I'd recommend checking with your tax professional or looking into comprehensive financial planning software that can factor in multiple variables like current taxes, future financial aid impacts, and college cost projections. Some online calculators exist, but given the complexity of your situation with kiddie tax, FAFSA implications, and long-term planning, you might benefit from professional guidance to make sure you're optimizing the right variables. Thanks for catching that - it's important to be accurate about these tax rules since the implications are so significant!

Haven't gotten any letters yet but ill def keep an eye out. And ima check out that AI thing rn, thanks!

You can definitely use software like TurboTax for prior years! They keep old versions available, though you might have to pay for them separately. I did my 2021 and 2022 returns this way a few months ago. Just remember you'll still need to print and mail the completed returns since e-filing is closed for those years.

@Dylan Campbell For missing 1099s and other tax documents, you can request copies directly from the IRS using Form 4506-T Request (for Transcript of Tax Return .)This will give you a transcript showing what income documents were reported to the IRS for each tax year. It s'free and you can request it online, by mail, or by phone. You can also contact your former employers, banks, or other institutions directly - they re'usually required to keep copies of tax documents for several years. Many banks and financial institutions also have online portals where you can access historical tax documents. Another option is to check if you saved any documents digitally - email attachments, cloud storage, etc. Sometimes we forget we downloaded PDFs of our tax documents. The IRS transcript is probably your best bet though, since it will show you exactly what they have on file for your income each year. Just make sure to allow a few weeks for processing time when you request it.

Great question about missing documents! You can actually request copies of most tax documents directly from the IRS if you're missing them. Form 4506-T lets you request transcripts of your tax information, including W-2s and 1099s that were filed with the IRS for specific years. You can also contact your former employers directly - they're required to keep payroll records for several years and can often reissue W-2s. For 1099s, reach out to any banks, investment companies, or clients you worked with during those years. Another option is to check if you have old bank statements or emails that might show deposits from freelance work or investment income - this can help you remember who might have issued 1099s that you need to track down. The IRS transcript is probably your best bet though, since it will show you exactly what income documents they have on file for each year. That way you'll know if you're missing anything important before you file.

Unfortunately, there's no way to recover your old Self-Select PIN if you've forgotten it. You'll need to reset it by using 00000 as your PIN and entering your prior year AGI for verification instead. The IRS system will then let you create a new Self-Select PIN for future years if you want. Just make sure you have your 2023 AGI amount exactly right - you can find it on line 11 of your Form 1040 from last year. If you're off by even a dollar, it'll reject again. And yes, definitely try the IRS Free File system if TurboTax keeps giving you trouble. Sometimes the direct route works better, especially during peak filing season when third-party systems can have connectivity issues.

Unfortunately, there's no way to recover a forgotten Self-Select PIN from previous years. If you can't remember it, your best bet is to use your prior year AGI as the electronic signature method instead. When you get to the signature section in your tax software, choose the AGI option rather than the Self-Select PIN option, and enter your 2023 Adjusted Gross Income exactly as it appears on your filed return (you can find this on line 11 of your Form 1040). Then the PIN field should automatically populate as 00000. This is actually the more common method anyway, so don't worry about "resetting" anything - you're just switching to a different verification method that the IRS accepts.