Just wanted to add some important context here - you absolutely can still claim those stimulus payments through the Recovery Rebate Credit when you file your back taxes. However, be aware that the IRS has been extra thorough in reviewing returns that claim these credits, so make sure you have documentation of what you actually received (or didn't receive). If you're unsure about which payments you got, you can request your Account Transcript from the IRS online at irs.gov - it'll show all payments made to you. This will help you avoid claiming incorrect amounts which could delay your refund or trigger correspondence from the IRS. Also, since you mentioned being out of work, don't forget to look into other credits you might be eligible for like the Earned Income Tax Credit (if you had some income) or the Child Tax Credit if you have kids. These can significantly increase your refund beyond just the stimulus payments.

Just wanted to share my experience since I was in almost the exact same situation last year. I hadn't filed 2020 or 2021 taxes and was panicking about missing out on the stimulus money. Here's what I learned: First, you definitely CAN still get the stimulus payments through the Recovery Rebate Credit when you file your back taxes. The money comes as part of your tax refund, not as separate stimulus checks. Second, time is critical! For 2020 taxes, you only have until May 17, 2024 to claim any refund (including stimulus money). That's coming up fast! For 2021, you have until April 18, 2025. I ended up getting my Account Transcript from the IRS website to see exactly which payments I had received (turned out I got one partial payment I'd forgotten about). This was crucial because the IRS will delay your refund if you claim the wrong amount. Filed both years in February and got my refunds about 10 weeks later - much slower than normal but I did get the full stimulus amounts I was eligible for. The wait was nerve-wracking but totally worth it. Don't give up hope, just make sure you file accurately and as soon as possible!

I'm surprised nobody has mentioned the potential for basis adjustment due to the "kiddie tax" that might have applied while the shares were in the UGMA account. If the custodial account generated dividends or other income that exceeded certain thresholds while you were a minor, there could be implications for your basis calculation. Also, don't forget to check if there were any return of capital distributions over the years that would have reduced your basis. With shares held this long, it's surprisingly common.

This is exactly the type of complex situation where getting professional help makes sense. Between the original employee stock options, the UGMA transfer, multiple corporate actions (two mergers!), and decades of potential dividend reinvestments, you're dealing with a multi-layered basis calculation that could easily result in overpaying taxes if handled incorrectly. A few additional things to consider that others haven't mentioned: 1. Check if your brokerage has any historical records from when the shares were transferred in 2018. Sometimes they capture basis information from custodial accounts even if it's not immediately visible. 2. Contact the current company's investor relations department - they often maintain historical information about corporate actions, stock splits, and merger terms going back decades. This documentation will be crucial for your basis calculations. 3. If your father still has any old tax returns from around 1992 when he exercised the options, those might show the income he recognized, which would help establish his original basis. 4. Don't overlook state tax implications - some states have different rules for gift basis than federal tax law. Given the potential tax savings involved with shares held for 30+ years, it's probably worth investing in proper documentation and calculation rather than guessing. The IRS is pretty strict about substantiating basis claims, especially on large gains from old securities.

Has anyone used TurboTax to figure this out? I'm in literally the same situation (26, lived with parents most of 2024, made under the threshold) and the software keeps giving me conflicting answers about my status when I try different paths.

I went through this exact situation two years ago! The key thing that helped me was creating a detailed support calculation spreadsheet. I tracked everything - rent value for the months I lived with my parents, groceries they bought, utilities, even car insurance they paid. What surprised me was that the "fair rental value" of living at home was way higher than I expected - like $800/month in my area. When I added up ALL the support (not just cash), my parents had definitely provided more than half my total support for the year, even though I was working. The good news is you have options here. Even if you qualify as a Qualifying Relative, your parents can choose not to claim you if that works better for your family's overall tax situation. But as others mentioned, you'd still need to check the box saying you CAN be claimed. I ended up having my parents claim me because their tax savings were bigger than what I would have gotten filing independently, and they shared some of that savings with me. My advice: sit down with your parents, calculate the actual numbers for both scenarios, and make the decision that benefits your family most overall.

This thread has been incredibly helpful! I'm actually in a very similar situation - inherited a whole life policy that my uncle had been paying into for about 20 years before he passed. I was planning to just surrender it and report the full amount as taxable income, but after reading through all these comments, I realize I need to get the complete premium payment history first. The tips about using Claimyr to get through to the right department at the insurance company seem really valuable. I've been dreading dealing with customer service, but it sounds like getting to their "policy services" or "tax basis research" team makes all the difference. One question though - since I inherited this policy rather than received it as a gift while my uncle was alive, does that change how the basis is calculated? From what I understand, inherited policies get a "stepped-up basis" to fair market value at death, but I want to make sure I'm not missing anything before I surrender.

This is such a helpful discussion! I'm dealing with something similar but with a twist - my mom gifted me her whole life policy about 3 years ago, but she had actually let it lapse for about 6 months in 2019 before reinstating it. I'm wondering if that lapse affects how I calculate the tax basis when I surrender? I've been paying the premiums since she gifted it to me, and I have records of what I've paid, but I'm not sure if that 6-month gap where no premiums were paid changes anything about carrying forward her basis. The policy definitely lost some cash value during the lapse period before being reinstated. Has anyone dealt with a previously lapsed policy before? I'm worried the IRS might treat this differently than a continuous policy when it comes to the gifted basis rules.

Don't forget about the "die" part of this strategy lol. Make sure you have proper estate planning with a good attorney who understands step-up basis rules. My father-in-law did this for years but didn't update his trust after the 2017 tax law changes, and it created a mess for the family to untangle after he passed. I think this strategy makes the most sense for people in their 50s+ who have substantial appreciated assets and are unlikely to need to sell them during their lifetime. For younger investors, the benefit is less clear since the time horizon until the "die" part means decades of interest payments.

I've been implementing a modified version of this strategy for the past 3 years, and it's been working well so far. One thing I haven't seen mentioned yet is the importance of having multiple credit facilities to reduce concentration risk. I use a combination of portfolio margin loans and securities-based lines of credit from different brokers. The key lesson I learned is to always stress-test your leverage ratios against worst-case scenarios. I maintain detailed spreadsheets modeling what happens to my loan-to-value ratios under various market conditions (2008-level crash, interest rate spikes, etc.). This helped me realize I needed to keep my overall leverage much lower than I initially planned. Also, consider the psychological aspect - watching your portfolio fluctuate while carrying significant debt can be stressful. Make sure you're truly comfortable with the risk before going all-in. The tax benefits are real, but they're not worth losing sleep over potential margin calls.