Just a heads up for anyone new to ESPPs - the taxation gets even more complicated if your plan has a "lookback provision" where you get the discount based on either the price at the beginning or end of the offering period, whichever is lower. In those cases, you might actually have MORE than just the straight 15% discount counted as ordinary income. If the stock price increased during the offering period and you get to use the lower beginning price, that additional discount also counts as ordinary income.

I've been through this exact situation and want to emphasize something that might not be obvious - make sure you understand your company's specific ESPP terms before assuming the standard 15% discount applies the same way everywhere. Some plans calculate the discount differently (like using the lower of beginning/ending prices as mentioned), and some companies withhold taxes on the discount automatically while others don't. I learned this the hard way when I assumed my situation was identical to what I read online. Also, keep detailed records of your purchase dates, fair market values, and actual amounts paid. You'll need these for Form 8949, and it's much easier to track this as you go rather than trying to reconstruct it at tax time. Your brokerage statements might not have all the details you need for proper tax reporting. One more tip - if you're planning to do immediate sales regularly, consider the transaction costs. Frequent small sales can eat into your gains pretty quickly depending on your broker's fee structure.

I also have the same issue but my code 150 have a future date , code 810 is some months ago

Hey Greg! I went through something super similar last year. The 810 freeze is definitely frustrating but you're on the right track having done the in-person verification. Those codes 766 and 768 are actually good signs - they show your credits are being processed and applied to your account. The 4/15/24 date you're seeing is just the tax filing deadline, not your refund date unfortunately. After identity verification, the IRS usually takes 6-9 weeks to lift the freeze and process your refund. Keep checking your transcript for when that 810 code disappears - once it's gone and you see an 846 code, that's when you'll have your actual refund date! The waiting is the worst part but you're definitely moving in the right direction 👍

Has your son received any letters from the IRS over the years? The fact that they haven't reached out makes me think he's probably due refunds rather than owing money. But regardless, fixing this now is smart before they do eventually notice. My advice is to focus on the last 3 tax years first (2022, 2023, 2024) since those are the only ones where he can still get refunds. Then deal with 2019-2021 to get fully compliant, but understand those refunds are likely lost forever.

First, take a deep breath - this is absolutely manageable! Your son isn't the first person in this situation, and he won't be the last. The IRS deals with these cases regularly. Here's my practical step-by-step approach: 1. **Get the wage transcripts first** - Call the IRS at 800-908-9946 or use their online "Get Transcript" tool. You'll need transcripts for at least the last 6 years to get compliant. 2. **Start with 2022-2024** - These are the only years he can still claim refunds for, so prioritize these. If he's owed money (which sounds likely), there are zero penalties for filing late. 3. **Don't stress about the older years initially** - Yes, he should file them for compliance, but any refunds from 2018 and earlier are gone forever, so focus your energy on the recoverable money first. 4. **Consider getting professional help** - Given that this spans 15 years and potentially involves multiple employers, a tax professional might save you time and stress. Many will do a free consultation to assess the situation. The key thing to remember: if he's been having taxes withheld and making modest wages, he's likely owed money, not the other way around. The IRS wants people to get compliant - they're not looking to destroy someone who's trying to fix their situation voluntarily.

I went through this exact same situation with Form 3531 about 6 months ago! The signature issue is incredibly common - even when you think you signed everything properly, sometimes the ink doesn't show up clearly when they scan it, or you might have missed signing a schedule attachment. For the address situation, I was confused about this too until I called the IRS. They explained that even though you moved after filing, they want your return to reflect your current address in their system so all future correspondence about that specific tax year goes to the right place. It's more of an administrative update than anything punitive. You have a couple good options here: 1) Fix the paper forms and mail them back (your February filing date is preserved), or 2) E-file instead since your paper return was technically rejected. I went with e-filing and it was SO much faster - got my refund in about 2 weeks instead of waiting months for paper processing. If you do e-file, just use your current address from when you moved in July. Since you already updated your address with the IRS online, this will actually solve both the signature and address issues at once. The electronic signature takes care of the signing problem, and having your current address on the return matches their records. Don't stress too much - this is a very fixable situation and won't affect your refund timeline as long as you respond promptly!

I've been following this thread closely since I'm dealing with a very similar Form 3531 situation right now! Thank you to everyone who shared their experiences - it's been incredibly helpful to see so many people who went through the exact same thing. Based on all the advice here, I'm convinced that e-filing is the way to go. The idea of getting my refund in 2-3 weeks instead of potentially waiting months for paper processing is really appealing, especially since I've already been waiting since February like the original poster. One thing I want to emphasize for anyone else reading this thread: make sure you're using black ink if you do decide to go the paper correction route. I learned this the hard way on a different form last year - apparently blue ink sometimes doesn't scan clearly in their systems, which can trigger the signature issue even when you think you signed everything properly. The address situation still seems confusing to me though. If I moved after filing but before receiving the Form 3531, should I use my old address (from when I originally filed) or my current address when e-filing? I've seen conflicting advice on this point.

Has anyone tried using one of those debt settlement companies? I see ads for them all the time promising to cut credit card debt by 50% or more. Would that be better than touching the 401k?

I completely understand the pressure you're feeling - high interest credit card debt can be absolutely crushing. Before touching your 401k, I'd strongly recommend exploring every other option first. Here's the brutal math: if you're under 59½ and withdraw $58,700, you'll likely pay around 22-24% in federal taxes plus 10% early withdrawal penalty, plus any state taxes. That could mean losing $20,000+ right off the top, leaving you with maybe $35,000-40,000 to pay down debt. Since you mentioned your business is generating income again, have you tried these approaches? 1) Contact each credit card company's hardship department directly - explain your situation and ask for payment plans or temporary interest rate reductions. 2) Look into nonprofit credit counseling (try NFCC.org) - they can sometimes negotiate lower rates across all your cards. 3) Check if your 401k plan allows loans - you'd pay interest to yourself instead of losing money to penalties. The 401k withdrawal might feel like a quick fix, but it could cost you decades of retirement growth. Your future self will thank you for exploring alternatives first.