Important question: when did you leave your company compared to when you exercised the options? If there was a significant gap (like more than 3 months), there might be an issue with the 409A valuation they used for the FMV. Companies are supposed to use updated valuations, and if they used an outdated one, you might have grounds to dispute the valuation with the IRS.

This is a really complex situation that highlights why equity compensation taxation is so tricky. Based on what you've described, it sounds like there were multiple communication failures between SecFi, your former employer, and potentially even your accountant. One thing that stands out is that you mentioned SecFi told you taxes were "covered" but then your former employer reported wages on a W-2. This suggests there might have been withholding taxes paid (which SecFi may have included in their financing) but the W-2 income wasn't properly accounted for on your tax return. A few immediate steps I'd recommend: 1. Get a wage and income transcript from the IRS for 2022 - this will show exactly what was reported and any withholding credits you might be entitled to 2. Request detailed documentation from SecFi showing exactly what taxes were withheld and paid on your behalf 3. File an amended return (Form 1040X) to properly report the W-2 income, which should also credit any withholding that was already paid The good news is that if taxes were actually withheld but not credited to your account, you might not owe as much as you think. The bad news is that NSO exercises almost always result in a significant tax liability that goes beyond just withholding. Going forward, always assume you'll get a W-2 for NSO exercises and that additional taxes beyond withholding will be owed. These financing companies are in the business of providing capital, not tax advice, regardless of what their reps might say informally.

Has anyone mentioned the at-risk rules yet? Even if you could somehow get around the passive activity loss limitations, you'd still need to have "at-risk" basis in the LLC to claim the losses. Did you or your wife actually contribute cash or property to the LLC, or personally guarantee any loans? Without at-risk basis, you can't take the losses even if they weren't passive.

Just to add another perspective on this - make sure you're also considering the state tax implications carefully. I had a similar situation with an out-of-state LLC and ended up owing more in nonresident state taxes than I expected because the state where the property was located didn't allow the same loss carryforward rules as the federal return. Also, keep detailed records of all your suspended passive losses. I use a simple spreadsheet to track mine year over year, including the original source and any partial usage. It becomes really important when you eventually dispose of the property or generate passive income to offset against. The IRS doesn't send you a reminder of what you have suspended, so it's on you to track it properly. One last thought - if this hunting property ever generates rental income (like seasonal hunting leases), that would be passive income that could be offset by your suspended losses. Might be worth discussing with the family whether monetizing the property could help everyone's tax situation.

Don't wait! I had almost the exact same situation happen with my daughter's 529 (accidentally transferred $2000), and I noticed the mistake right away but thought "I'll deal with it tomorrow" - big mistake. The money got invested overnight based on my pre-set allocations, and then I had to deal with the earnings. Ended up paying a small penalty but it was such a headache with the tax reporting. Just call them ASAP!

I'm glad you caught this mistake so quickly! I went through something similar last year when I accidentally contributed to the wrong 529 account (my nephew's instead of my son's). The key is definitely acting fast before any automatic investment happens. Since you called within 30 minutes, you should be fine. Most 529 plans have a grace period before they invest new contributions - usually 24-48 hours. Your plan administrator was correct about the no-tax-consequences rule as long as it's still in cash. One tip: once you get this sorted out, consider setting up account nicknames or alerts in your banking app to prevent this from happening again. I learned that lesson the hard way! Also, some banks let you set up confirmation screens for transfers above certain amounts, which has saved me from similar mistakes.

I used TT for years but switched to FreeTaxUSA after the guarantee fiasco and it's been so much better. Paid $15 total for what TurboTax wanted $129 for lol

I had the exact same experience with TurboTax's "satisfaction guarantee" last year! What really got me was how they plaster that guarantee all over their marketing but bury the exclusions in tiny print that you only see after you've already paid. I ended up having to escalate through multiple customer service reps before anyone would even acknowledge that their advertising was misleading. The worst part is they know exactly what they're doing - their customer service scripts are clearly designed to wear you down and make you give up. I finally got my refund after threatening to report them to my state's attorney general office, but it took weeks of back and forth. For anyone still dealing with this, document EVERYTHING. Screenshot every page that shows the guarantee without clear limitations, save all your chat transcripts, and don't let them transfer you around in circles. Ask to speak to a supervisor immediately and reference their own terms of service if they try to claim you don't qualify. It's ridiculous that we have to fight this hard just to get what they advertised, but unfortunately that seems to be TurboTax's business model now.

Has anyone used TurboTax for reporting this kind of thing? I'm confused about where to even put this information when I file!

I went through something very similar last year with a charity auction I organized! The most important thing is to establish that you were acting as an agent/conduit for the charity from the beginning, not as someone who received income and then decided to donate it. Here's what saved me: I got a signed letter from the 501(c)(3) organization stating that I was authorized to collect funds on their behalf as a volunteer fundraiser, and that all net proceeds were always intended for their organization. This letter should be dated close to when your event occurred (not just now when you're filing taxes). When reporting, you'll want to show the gross receipts as "Other Income" on Schedule 1, but then you can offset it with the charitable deduction. The key documentation is: 1) All your expense receipts totaling $2,300, 2) The charity acknowledgment letter, 3) Bank records showing the $3,900 transfer to the charity, and 4) A simple written statement explaining your role as volunteer organizer. Don't worry too much - the IRS understands volunteer fundraising is common. Just make sure you have solid paper trail showing you never personally benefited and were always acting on behalf of the charity.