Just to add another perspective - one option no one's mentioned is adjusting your vesting schedule while the company valuation is still low. If you accelerate vesting now, you'll recognize ordinary income on the current (presumably low) value difference between what you paid and fair market value. This won't fix the missed 83(b), but could minimize the tax impact if done while company valuation is still close to what you paid. You'll want a proper 409A valuation to document the current fair market value to support this approach.

This is a tough situation but you're not completely out of options. I've seen similar cases where founders had some success with a few different approaches: 1. **Document your reasonable cause**: Even though the IRS is strict about the 30-day rule, you should still prepare documentation showing you had reasonable cause for the delay (misunderstanding the timeline, reliance on incorrect advice, etc.). While it rarely works for 83(b) elections, having this documentation ready could help if you ever face penalties. 2. **Consider a Section 83(b) "protective election"**: Some tax advisors suggest filing the election anyway with a cover letter explaining the circumstances, even though you're past the deadline. The IRS will likely reject it, but it creates a paper trail showing your intent and good faith effort. 3. **Restructure now while valuation is low**: Since your company hasn't increased much in value, this is actually the best time to explore restructuring options. The tax consequences of canceling and reissuing shares would be minimal at current valuations. 4. **Plan for the future**: Make sure you understand exactly how the missed election will affect you at different exit scenarios (acquisition, IPO, etc.) so you can plan accordingly. The key is acting quickly while your company valuation is still low. Once it starts growing, your options become much more limited and expensive.

Has anyone successfully completed this through the online application portal? I tried but got stuck at the "Who owns the LLC?" question. There's no option for "trust" or "partnership" - just individuals and existing corporations. Do I seriously have to use the paper form and wait weeks for processing?

I've been dealing with this exact scenario for my practice and wanted to add some clarification on the responsible party requirements. The IRS actually issued updated guidance in 2016 (Rev. Proc. 2016-21) that addresses this specific situation. For disregarded entities owned by non-individuals, the responsible party must be an individual who has "significant control" over the owning entity. This means: - For a trust-owned LLC: Use a trustee (not a beneficiary) - For a partnership-owned LLC: Use a general partner or managing member - For a corporation-owned LLC: Use an officer, director, or controlling shareholder The key is that this individual must have authority to make decisions for the owning entity. You're not claiming to be the owner - you're identifying yourself as the controlling person of the actual owner. Also, make sure to include a brief explanatory statement with your paper application describing the ownership structure. Something like: "Single-member LLC owned by [Name of Trust/Partnership], disregarded entity for federal tax purposes." This helps prevent processing delays. The paper route is definitely your best bet here. The online system hasn't caught up with these complex structures yet.

Has anyone used FreeTaxUSA for filing prior year returns? I heard they charge like $15 per state but federal is free even for old returns.

I went through almost the exact same situation a couple years ago! Was overwhelmed with life stuff and let my taxes slide for 2019 and 2020. The IRS Wage and Income Transcript that Mateo mentioned is absolutely the way to go - it's like a lifesaver when you have missing W2s. One thing I'd add is that when you're dealing with a company that went out of business, sometimes their payroll records got transferred to whoever handled their final business affairs (like a bankruptcy trustee or accounting firm). You might try searching online for any notices about the company's closure to see if there's contact info for getting final tax documents. Also, don't stress too much about being late - the IRS is surprisingly understanding when you owe them money versus when they owe you money. Since you think you'll get refunds, they're not going to come after you with penalties. Just get it sorted before that 3-year deadline Zoe mentioned! Good luck getting back on your feet - you've got this! 💪

Does anyone know if you can transfer a 529 plan from a parent to a grandparent? My situation is backwards from most - I opened 529s for my grandkids but now their parents make more money than me and could benefit from the state tax deduction more than I can.

Great question! I went through this exact decision a few years ago with my kids. Definitely keep the 529 plans in your name (or yours and your wife's) with the twins as beneficiaries - don't put them directly in the kids' names. Here's why this matters for your situation: Since you mentioned being in a higher tax bracket, you'll want to maximize any state tax deductions available. Most states that offer 529 deductions only give them to the account owner, so having the plans in your names ensures you can claim those deductions. Also, for financial aid purposes down the road, parent-owned 529s are assessed at only 5.64% when calculating expected family contribution, versus 20% if the student owns the account. That's a huge difference that could affect aid eligibility. One more benefit - keeping ownership gives you flexibility. If one twin gets a full scholarship or decides not to go to college, you can easily change the beneficiary to the other twin or even use it for graduate school later. You maintain complete control over the funds until they're withdrawn for qualified expenses. The tax advantages (tax-free growth and tax-free withdrawals for education) are the same regardless of ownership structure, so there's really no downside to the parent-owned approach.

Thanks for starting this thread! I'm in a similar boat - filed my IL return on March 8th and still waiting. The divorce filing status change definitely seems to add extra processing time. I've been using the IL Where's My Refund tool religiously, but it's been stuck on "Your return is being processed" for over 3 weeks now. Based on what everyone's sharing here, it sounds like we're right in that normal window, which is reassuring. The batched deposit schedule on Tuesdays/Fridays is really helpful to know - I'll stop checking my account every single day! 😅 Has anyone noticed if the IL DoR sends any email notifications when your refund is actually approved and scheduled for deposit? Or do you just wake up to find it in your account?

As a newcomer to this community, I wanted to share my recent Illinois refund experience that might help others! I filed my IL return on February 28th (also post-divorce, changing from MFJ to Single) and just received my refund yesterday - exactly 22 days from acceptance to deposit. A few things I learned during the process: • The IL DoR customer service rep told me that filing status changes automatically add about 7-10 days to processing time for verification purposes • My refund amount was under $500, which apparently keeps it in the "standard" processing queue rather than the higher-scrutiny review for larger amounts • The deposit hit my account on a Tuesday, confirming what others mentioned about the Tuesday/Friday batch schedule For those still waiting - hang in there! The timeline seems much more predictable this year compared to the horror stories I heard about 2023. The 2-4 week window really does seem accurate for most electronic filers, even with complications like divorce-related filing changes. Thanks to everyone who shared their experiences here - this thread was incredibly helpful during my anxious waiting period! 😅