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.

I went through something very similar with my NSO exercise through EquityBee (another financing platform) and want to share what I learned that might help you. The key thing I discovered is that these financing companies often use language like "taxes handled" or "taxes covered" when they really mean "mandatory withholding included in the financing amount." This is a crucial distinction because mandatory withholding (typically 22% federal + state rate) rarely covers your full tax liability, especially if you're in higher tax brackets or have other income. In my case, EquityBee included about $85k for "taxes" in the financing, but my actual tax liability ended up being $140k. The $85k was just the withholding that went to the IRS, but I still owed the additional $55k when I filed my return. What saved me was keeping detailed records of all communications with the financing company. When I had written emails stating "all taxes will be handled," I was able to use those to negotiate a partial reimbursement for the unexpected tax liability. It took months of back-and-forth, but they eventually covered about 60% of the difference. My advice: gather every email, text, and document from SecFi mentioning taxes being "covered" or "handled." If you have anything in writing that suggests full tax liability was covered (not just withholding), you may have leverage to negotiate with them. Also, definitely get that wage and income transcript - it will show you exactly what withholding credits you're entitled to, which could significantly reduce that $31k bill. The whole industry needs better disclosure about the difference between withholding and full tax liability. Too many people are getting blindsided by this.

The fact that they couldn't even tell you how to access Form 8949 for crypto is a huge red flag. I used Cash App Taxes (when it was still Credit Karma) and they completely messed up my foreign income reporting. I ended up getting a letter from the IRS and had to pay penalties. For anyone dealing with crypto, I HIGHLY recommend using a dedicated crypto tax software like Koinly or CoinTracker to generate your 8949 forms first, then input those totals into whatever tax software you use. That way you have documentation if you ever get audited.

I'm dealing with a similar nightmare with Cash App Taxes right now. Filed my return in February and just got a CP2000 notice from the IRS saying my crypto transactions were reported incorrectly. Cash App apparently didn't include some of my cost basis information properly, so the IRS thinks I owe way more than I actually do. Their customer support has been completely useless - they keep telling me to "just respond to the IRS notice" but won't explain how their software calculated my gains in the first place. I can't even see the actual Form 8949 they submitted on my behalf! Now I'm scrambling to gather all my transaction records to prove the correct cost basis to the IRS. This is exactly why transparency matters - you should always be able to see the actual tax forms being filed in your name. Lesson learned the hard way.

One option nobody's mentioned yet is TaxHawk - it's basically the same company as FreeTaxUSA but with a slightly different interface. Federal is free and state is $14.99 just like FreeTaxUSA. I've used it for 3 years with multiple 1099s and Schedule C. I like that they don't constantly try to upsell you on stuff you don't need. The interface is basic but gets the job done, and their help content is actually really clear for self-employment questions.

Watch out for the Free File income limits! I got burned last year thinking I qualified but my AGI was like $200 over the limit and ended up having to pay. The 2024 filing limit should be around $73k but check the IRS site to be sure. Also, if you go with FreeTaxUSA, search for coupons! I found a 25% off code that brought the state filing down to about $11. Every little bit helps when you're on a tight budget.

I'm dealing with something very similar right now and this thread has been incredibly helpful! Just wanted to add that if you paid through Direct Pay, you can actually look up your payment confirmation online at IRS.gov/payments even if you don't remember your confirmation number. You just need your SSN, payment amount, and the date you made the payment. I found my confirmation there and it showed that my payment was processed but somehow got applied to the wrong form type (they put it toward estimated taxes instead of my 1040 balance due). The confirmation page actually has a "Print" option that gives you an official-looking document with all the payment details that you can include with your response. One thing I learned from calling (after waiting 2 hours) is that if you respond in writing to the CP14, they're supposed to put a hold on any collection activity while they investigate. The agent told me to write "PAYMENT INQUIRY" at the top of my response letter in big letters so it gets routed to the right department faster. Also, if you're really stuck and the online account doesn't show your payment, try calling the automated payment line at 1-888-353-4537. You can check if your payment was processed without having to wait for a human agent.

This is incredibly stressful but you're definitely not alone in dealing with this! Based on all the great advice here, I'd recommend a multi-pronged approach to get this resolved quickly. First, definitely create that online account at IRS.gov if you haven't already - you might be able to see exactly where your payment ended up. Sometimes it's as simple as it being applied to the wrong tax year or form type. Second, gather ALL your documentation now - bank statement showing the withdrawal, any confirmation emails or numbers, screenshots of your online banking, everything. Make copies (never send originals) and respond to that CP14 notice in writing within their deadline. Write "PAYMENT INQUIRY" at the top like Mateo suggested. Third, try that automated payment line at 1-888-353-4537 to verify your payment was processed before trying to reach a human agent. The most important thing is to respond within their timeframe even if it's just to say "I already paid, here's my proof" - this should put a hold on any collection activity while they investigate. I know it's frustrating when you KNOW you paid, but based on everyone's experiences here, this does get resolved once they locate your payment in their system. The IRS processing systems clearly have issues matching payments correctly, especially around filing deadlines. Hang in there!

Has anyone actually been audited over donation timing like this? I'm wondering how strict the IRS really is about this December/January thing. They can't possibly check every donation date, right?

I work in tax preparation and see this exact scenario all the time. The consensus here is correct - for ACH transfers initiated on December 31st, what matters is whether you could cancel the transaction after submitting it. Most banks don't allow you to cancel ACH transfers once they're submitted, which means you "made" the donation in 2024 even though it processed in January. However, I'd recommend keeping documentation of both the initiation date (December 31) AND the processing date (January) in case you're ever questioned. Bank screenshots showing the pending transaction on December 31st would be ideal proof that you surrendered control of the funds in 2024. For your $2,300 in donations, this documentation becomes especially important since it's a significant amount. The IRS does spot-check charitable deductions, and having clear proof of timing will save you headaches if they ever ask questions.