This is a really helpful discussion! As someone new to the complexities of S-Corp retirement planning, I'm learning a lot from everyone's experiences. One question that comes to mind - has anyone dealt with the timing aspects of profit sharing contributions? I understand the S-Corp can contribute up to 25% of W-2 wages, but are there specific deadlines for making these contributions? Can they be made after year-end but before the tax filing deadline (with extensions), similar to SEP-IRA contributions? Also, given all the warnings about controlled group rules, it seems like getting a professional determination letter or opinion from a qualified plan attorney might be worth the investment upfront rather than risking an audit issue later. Has anyone gone that route for peace of mind? The medical practice structure described here sounds quite common, so I imagine there are established best practices that practitioners have developed over time.

As someone who recently navigated a similar situation with my own medical practice S-Corp, I wanted to share a few practical considerations that might help. First, regarding implementation timing - don't feel pressured to rush this for 2025. While your CPA mentioned potential tax savings, it's better to get the structure right than to hastily implement something that could create compliance issues later. The profit sharing option will still be available next year once you've properly evaluated all the moving parts. Second, I'd strongly recommend getting clarity on the exact W-2 amount from your wife's S-Corp before calculating contribution limits. The 25% limit applies to her S-Corp W-2 wages specifically, not to the guaranteed payments from the LLC. This distinction becomes important when you're maximizing contributions across multiple retirement vehicles. Finally, consider having a three-way conversation between yourself, your CPA, and the current 401k administrator. I found this approach eliminated a lot of back-and-forth and confusion about how the different contribution streams would work together. The administrator can often provide specific guidance on how to structure the employer contributions from the S-Corp level while coordinating with existing employee deferrals. Don't be embarrassed about asking your CPA for clarification - these multi-entity medical practice structures are genuinely complex, and even experienced professionals sometimes need to work through the details multiple times to get them right!

One important thing nobody mentioned - make sure you're looking at the correct IP PIN for the current tax year! The IRS issues new IP PINs every year, so don't use last year's PIN for this year's return. This is a common mistake people make.

I went through this exact same situation last year with H&R Block desktop and my first IP PIN! I was so nervous about messing something up, but it actually went much smoother than I expected. The key thing is to have your IP PIN letter handy when you're ready to e-file. H&R Block will walk you through it step by step - first the AGI verification, then later it will specifically ask if you have an IP PIN and where to enter it. Don't try to enter it anywhere else in the software, just wait for the prompt. One tip: double-check that you're using the current year's PIN (the one you should have received in January 2025 for your 2024 return). And if for some reason your return gets rejected, don't panic - it's usually just a typo in the PIN entry and you can fix it and resubmit. The IP PIN actually makes your return more secure, so you're doing the right thing by keeping it active. Good luck with your filing!

Has anyone actually tried to do what OP is asking on their tax return? I'm curious if the tax software would even let you. When I use TurboTax, it seems to automatically apply as much investment interest as possible against my investment income.

I appreciate everyone's thorough discussion on this topic. As someone who works in tax preparation, I can confirm what others have said - the IRS does NOT allow voluntary deferral of investment interest expense when you have sufficient investment income to use it in the current year. The key thing to understand is that Form 4952 is a calculation form, not an election form. Line 5 (deductible investment interest expense) is determined by the lesser of your investment interest expense or your net investment income - there's no checkbox or option to voluntarily reduce this amount. However, the suggestion about managing the timing of income recognition is spot-on. You do have control over when you realize capital gains by choosing when to sell investments. If you're really looking to defer the tax benefit, consider whether you truly need to realize all those gains this year, or if some could be pushed to next year when the deduction might be more valuable to you. Just remember that any tax planning strategy should consider your overall financial picture, not just one deduction in isolation.

I went through this exact same situation about 3 years ago when I started doing freelance web development alongside my regular job. The stress is real, but you're going to be okay! First, don't beat yourself up - this is incredibly common for new 1099 workers. The IRS knows this happens frequently, which is why they have systems in place to handle it. Here's what worked for me: I calculated what I should have paid for each missed quarter using Form 1040-ES and made all the payments at once. Yes, there were penalties, but they were much smaller than I feared - about $240 total on roughly $35k of 1099 income. The key is acting quickly now rather than waiting until tax season. With your monthly income of $2,800-3,200, you're looking at roughly $33k-38k annually from the 1099 work. Set aside about 30-35% of that for taxes (both income tax and self-employment tax). So you'd want to pay around $2,500-3,000 per quarter. One tip: consider increasing your W2 withholding instead of making quarterly payments going forward. I ended up doing this and it's so much easier - just fill out a new W4 and have extra withheld from each paycheck. The IRS doesn't care where the money comes from as long as you're paying enough throughout the year. You've got this! Take action now and you'll minimize any penalties.

I completely understand your panic - I was in the exact same situation when I started doing freelance graphic design work alongside my W2 job! The quarterly payment requirement really catches people off guard. Here's the reality: yes, you'll likely face some penalties for missing the quarterly payments, but they're usually much more manageable than people expect. The IRS penalty for underpayment is currently around 8% annually on the amount you should have paid, calculated from when each payment was due. With your 1099 income of $2,800-3,200 monthly, you're looking at roughly $34k-38k annually. You should generally set aside about 30-35% for taxes (this covers both income tax and the 15.3% self-employment tax for Social Security and Medicare). My advice: 1. Calculate what you owe for the missed quarters using Form 1040-ES 2. Make the payments ASAP to minimize additional penalty accrual 3. Consider increasing your W2 withholding going forward instead of quarterly payments - just fill out a new W4 with an extra amount per paycheck The good news is that if you've been setting money aside, you're already ahead of many people in this situation. Don't let the stress consume you - take action now and you'll get through this just fine. The IRS deals with this scenario constantly, especially with the growing gig economy.

I've been dealing with the 570 code for about 6 weeks now and wanted to share what I've learned from calling the IRS multiple times. The key insight is that not all 570 codes are created equal - some are automated system holds (usually resolve faster) while others require manual review by an examiner (can take much longer). When I finally got through to an agent, they explained that mine was flagged for income verification because I had some freelance 1099 income that didn't match their records exactly. The agent was able to see that my supporting documents were already in the system and estimated another 2-3 weeks for resolution. So my advice: if you're past the 21-day mark and haven't received any notices, it's definitely worth the phone call hassle to get specifics about your case. The uncertainty is often worse than the actual issue!

I'm currently going through this exact situation! Filed on March 3rd and got hit with the 570 code on March 18th - so I'm coming up on 5 weeks now. What's been driving me crazy is that I also haven't received any notices or correspondence from the IRS, so I'm completely in the dark about what triggered the hold. Like you, I have some investment decisions that are time-sensitive and the uncertainty is really stressing me out. I've been reading through all these comments and it's both reassuring and terrifying to see such a wide range of timelines - from 9 days to 2+ months! I think I'm finally going to follow everyone's advice here and call the IRS this week, even if it means sitting on hold for hours. At least then I'll know if it's something simple like income verification or if there's a bigger issue. Thanks for posting this question - it's been incredibly helpful to see everyone's experiences and realize this is way more common than I thought. Will definitely update here if I learn anything useful from calling! 📞