I switched to Square Payroll last year and they definitely handle the reporting, but just FYI - they messed up my state unemployment tax rate. Double check that they have your correct SUTA rate if your state assigns individual rates to businesses. That's the one thing they got wrong for me.

Thanks everyone for all the helpful info! @Logan - I've been using Square Payroll for about 6 months now and can confirm they do handle most of the federal reporting automatically. One thing I'd add is to make sure you verify your business information is correct in their system, especially your EIN and business address. I had a small typo in my EIN that caused a delay with my 941 filing until I caught it and got it corrected. Square's support was helpful in fixing it, but it's better to catch these things early. Also, definitely keep those separate records you mentioned - they've been super helpful when I needed to reference specific pay periods or double-check calculations.

What I ended up doing after facing this exact same issue was printing out Form 8863, filling it out by hand, scanning it, and then attaching it to my electronic return as a PDF. This bypassed the fillable form system's validation for that particular form while still allowing me to e-file the rest of my return. It's a workaround but it worked for me.

I've been dealing with this exact same Form 8863 rejection issue for the past week! After reading through all these suggestions, I tried the browser switching approach first (went from Safari to Firefox) and that actually fixed it for me. For anyone still struggling, here's what I learned from this thread and my own experience: 1. Try a different browser first - it's the easiest fix 2. Make sure you're filling out BOTH 22a and 22b sections even if you only attended one school 3. If checkboxes aren't working, try typing "X" instead of clicking 4. As a last resort, the print/scan/attach method works The whole Free File Fillable Forms system really needs an overhaul. These rejection issues seem way too common for such a basic form. Thanks everyone for sharing your solutions - this thread probably saved dozens of people from having to mail in their returns!

whatever u do dont ignore it. i did and now im stuck paying wayyy more in penalties and interest. setup that payment plan asap!

I went through this exact situation last year. The key is acting fast - once your refund is processed and sent to Treasury, it's much harder to get back. Most states allow you to set up payment plans online through their unemployment portal, but you need to do it BEFORE they submit your debt to the Treasury Offset Program. Also, make sure to get any payment agreement in writing. Some states will remove you from the offset list once you're in good standing on a payment plan, but policies vary by state.

Look for ur cycle code once ur transcript shows up. Mine ends in 05 so I only update on Fridays

Same struggle here! 😅 Filed electronically 10 days ago and still seeing N/A on my transcript. Based on what others are saying about the Friday update cycles, I'm gonna wait until this Friday to check again instead of my current hourly refresh habit lol. Really hoping to see some movement soon - this waiting game is brutal!

I went through something similar with my startup equity in 2022. One thing to consider that hasn't been mentioned yet is the potential wash sale rules if you're also trading in your company's stock through secondary markets or employee stock purchase plans. Also, given your company's current situation (70% drop in valuation), you might want to look at Section 1202 qualified small business stock (QSBS) benefits. If your company qualifies, you could potentially exclude up to $10 million in gains from federal taxes when you eventually sell. This is another reason why exercising now at the lower FMV could be beneficial - it starts your 5-year holding period clock for QSBS. The key is making sure you have enough liquidity to cover both the exercise costs ($36,400 for 28,000 shares) and the tax bill (roughly $1.36M in ordinary income assuming you're in a high tax bracket). Don't forget about state taxes too - they can add significantly to your bill depending on where you live. Have you considered doing a partial exercise strategy? Maybe exercise 25% of your vested shares now to start the capital gains clock, then reassess in 6-12 months based on how the company is performing?

Hi!  A lower 409A can make exercising NSOs more attractive from a tax perspective, but it’s only part of the decision (This is not personal tax advice). A few key points to consider: With NSOs, the spread at exercise is taxed as ordinary income. A lower FMV at exercise means a smaller taxable spread than if the valuation increases closer to IPO. You should review your specific situation with a tax advisor to understand the implications before exercising. That said, exercising still requires paying taxes now, even though liquidity may be years away, and an IPO is never guaranteed. Non-recourse financing can reduce the financial risk as there’s no out-of-pocket costs or personal recourse, but it usually means giving up some future upside, so it’s important to compare outcomes across different exit scenarios. Bottom line:A lower FMV can make early exercise more tax-efficient, but the right choice depends on liquidity risk, personal cash exposure, downside risk, among others. Many people choose to model scenarios or exercise only a portion rather than treating it as an all-or-nothing decision. Final reminder: When considering your options, you should also speak with your tax professional about the right approach for you.