Another option worth considering is filing Form 8832 first to elect to be taxed as a C Corporation, then immediately filing Form 2553 for S Corp status. Sometimes this two-step approach can work outside the normal S Corp election deadline. Talk to your accountant about this strategy - it's worked for some clients at our firm.

Don't forget that even if you successfully convert to an S Corp, you need to run payroll and pay yourself a "reasonable salary" before taking any distributions. Many people miss this and end up with IRS problems. My brother tried taking mostly distributions with a tiny salary and got hit with penalties for avoiding payroll taxes.

Just went thru this! That taxr.ai tool someone mentioned above is actually legit - told me exactly when my 420 would clear and it was spot on. Way better than waiting on hold with IRS for hours

Code 420 can be frustrating but hang in there! I'd recommend calling the Practitioner Priority Service line if you have a tax pro helping you, or try calling early morning (7-8am) for shorter wait times. Also keep checking your transcript weekly - sometimes the codes update before you get any mail. The fact that you only had W2 and child tax credit makes it likely just a routine verification that should clear up relatively quickly.

I'm still confused about this. Can I claim exempt just for December when I'm working all that overtime, then switch it back in January? Or is exempt an all-year thing?

I see a lot of confusion here about withholding vs. exemptions. Let me try to clear this up from a practical standpoint. The "exempt" checkbox on your W-4 is NOT a tool for managing cash flow during busy seasons. It's a very specific declaration that you expect ZERO federal tax liability for the entire year. This typically only applies to people earning very little (below the standard deduction threshold). If you're working overtime during the holidays and expect to owe taxes for the year, here are your legitimate options: 1. Adjust your withholding allowances on your W-4 to have less tax taken out (but still some) 2. Use the IRS withholding calculator or tools like those mentioned above to find the right balance 3. Accept that you'll get a larger refund when you file, but have less take-home pay now The key is being honest about your expected annual income. If you'll owe taxes for the year, claiming exempt is tax fraud, even if it's just for December. The IRS doesn't care that you need more cash for the holidays - they care about accurate withholding based on your actual tax situation. Better to adjust your withholding legally than risk penalties and a massive tax bill later.

FreeTaxUSA actually handles these retirement plan situations really well. I've had a similar setup with multiple retirement accounts including a non-qualified supplemental plan for years. One thing to watch for - make sure when entering your W2, you click the "additional information" section to enter Box 11 data. Some tax software hides the less common boxes and if you don't specifically look for them, you might miss entering that information. Also, if you're concerned about FICA taxes, remember that contributions to qualified plans like 401k reduce your FICA wages, but contributions to non-qualified plans (probably your supplemental retirement plan) do not reduce FICA wages. That's just how the tax code works.

I went through something very similar last year with my university benefits package! The key thing to understand is that Box 11 and Box 2 serve completely different purposes - comparing them directly doesn't really make sense. Box 11 shows distributions from your Supplemental Retirement Plan (which is likely a non-qualified deferred compensation plan), while Box 2 is just the federal income tax that was withheld from your paychecks throughout the year. The Box 11 amount represents actual money you received from the plan, which is why it can be much larger than your tax withholding. For FICA taxes, here's what matters: your regular 401k contributions reduce your FICA taxable wages, but your Supplemental Retirement Plan contributions typically don't. This is because non-qualified plans are subject to FICA taxes when you earn the money, not when you receive distributions later. When entering everything in FreeTaxUSA, make sure you input all the boxes from your W2 accurately - the software is designed to handle these multiple retirement plan scenarios correctly. The Box 11 amount should already be reflected in your Box 1 wages, so you won't be double-taxed on it. Your situation sounds completely normal for someone with multiple retirement benefits through a university!

Don't forget about the hospital bills and birthing costs! If either of you has a Health Savings Account (HSA), getting married could let you contribute more and use pre-tax dollars for all those medical expenses. The family contribution limit is way higher than individual ($7,750 vs $3,850 for 2024). Saved us tons when our baby came!

One thing to consider that hasn't been mentioned yet - if you do decide to get married, make sure to update your W-4 withholdings at work! Many couples forget this step and end up owing money at tax time or getting a huge refund (which means you gave the government an interest-free loan all year). With your combined income of $120,000 and a baby on the way, your tax situation will be quite different than when you were both single. The IRS has a good withholding calculator on their website, or you can use the new W-4 form which has been redesigned to be more accurate for married couples. Also, don't forget about Dependent Care FSA if either of your employers offers it - you can set aside up to $5,000 pre-tax for daycare expenses once the baby arrives. This is separate from the child care tax credit and can provide additional savings!