Just want to add my experience - I was in an almost identical situation last year. Had 3 years of unfiled taxes with both W-2 and 1099 income. I decided to DIY with tax software and regret it now. I thought I was saving money, but I missed several deductions that would have saved me thousands. I also messed up the estimated tax penalty calculations which caused more issues. Then I tried amending the returns myself which created an even bigger mess! Finally hired a tax pro who had to fix everything. Cost me way more in the end than if I'd just hired them at the beginning. Just my 2 cents, sometimes trying to save money costs more in the long run.

I want to share some practical advice from someone who went through a very similar situation recently. First, don't panic - this is absolutely manageable even though it feels overwhelming right now. For your unfiled returns (2015, 2018, 2020), the most important thing is getting them filed ASAP to stop the failure-to-file penalties from growing. These penalties are typically much higher than failure-to-pay penalties. Since you mentioned your returns are relatively straightforward, you could potentially handle the preparation yourself using prior year tax software. However, given that you have over $20k in total tax debt between your back taxes and unpaid 2023 estimated payments, I'd lean toward getting professional help for a few key reasons: 1. **Penalty abatement opportunities** - A tax pro can often get first-time penalty abatements or reasonable cause waivers that could save you hundreds or thousands 2. **Maximizing deductions** - Even "simple" 1099 work often has more deductible expenses than people realize (home office, mileage, equipment, etc.) 3. **Payment plan strategy** - They know how to structure installment agreements to get the best terms and can handle both your back taxes and 2023 shortfall in one comprehensive plan The $450 per year might seem expensive, but if they can reduce your tax liability by even 10-15% through proper deductions and penalty abatement, that fee pays for itself many times over. Plus, having everything handled correctly the first time prevents costly amendments later. For immediate next steps: gather all your tax documents for those years, and consider getting quotes from a few different tax professionals who specialize in tax resolution, not just basic tax prep.

One major tip I learned the hard way - don't just check the box in Step 2(c) on all your W4 forms! I did this with my 3 jobs and ended up having WAY too much withheld. That box basically tells each employer to withhold as if that job's income was your only income but at a higher single rate. The multiple jobs worksheet is much better but still not perfect. Personally, I'd recommend using the IRS tax withholding estimator online and updating your W4s quarterly if your income fluctuates.

This is such a common problem with multiple jobs! I went through something similar last year with 3 jobs. Here's what I learned that might help: First, you're absolutely right that the new W4 is way more complicated than the old allowance system, but it's actually more accurate once you figure it out. For your situation with 4 jobs where 2 weren't withholding anything, you definitely need to update ALL of them. My recommendation would be to start with the IRS Tax Withholding Estimator (it's free on the IRS website). It's specifically designed for multiple job situations and will give you exact instructions for each W4. You'll input all 4 jobs' expected income, and it calculates how much should be withheld from each. One thing to watch out for - if your jobs have very different pay rates, the calculator might suggest putting most of the extra withholding on your highest-paying job rather than spreading it equally. This actually works better for cash flow. Also, don't stress too much about getting it perfect right away. You can always adjust your W4s again if needed after a few paychecks. The key is getting something reasonable in place so you're not hit with another big tax bill next year!

One important thing that confused me about the 1095-C - it's different from a 1095-B! My spouse got a 1095-B from their insurance company and I got a 1095-C from my employer and they contain different information. Just wanted to point this out in case anyone else has both forms in their household.

Just want to chime in with a simple summary for anyone still confused! Your 1095-C form is basically just proof that your employer offered you health insurance coverage. You DON'T need to mail it in with your tax return or enter specific numbers from it into tax software. Think of it like a receipt - keep it with your tax records in case you ever need to prove you had qualifying health coverage. The main thing it helps with is showing the IRS that you met the health insurance requirement and shouldn't be penalized. If you're using tax software like TurboTax or H&R Block, they might ask if you had employer-sponsored health insurance, and you can just answer "yes" based on having this form. But you won't need to type in the specific codes or dollar amounts from the 1095-C itself.

I'm dealing with this exact same situation with my S-Corp that I started in 2023! Reading through all these responses has been incredibly eye-opening - I had no idea the IRS was so strict about the salary requirement even when you're not taking distributions. Like you, I've been reinvesting everything back into growing the business and haven't taken a penny out personally. I was actually hoping I could avoid the whole payroll setup complexity until I started taking money out, but it sounds like that's not an option. The documentation aspect that several people mentioned really resonates with me. I think that's been my biggest mistake - not keeping records of my decision-making process around compensation. I've been so focused on just running the business that I haven't been thinking about creating that paper trail for potential IRS scrutiny. Based on all the advice here, it sounds like I need to: 1) Research comparable salaries in my industry and area, 2) Set a reasonable but affordable salary (maybe 60-70% of market rate given cash flow constraints), 3) Document my reasoning with a formal board resolution, and 4) Set up proper payroll processing. This thread has been a huge wake-up call. Better to get compliant now than deal with potential reclassification and penalties later. Thanks everyone for sharing your experiences - this kind of real-world guidance is so much more helpful than trying to parse through IRS publications!

This is such a great thread - I've learned so much from everyone's experiences! I'm in a similar situation with my S-Corp (started in 2022, sole owner, reinvesting everything) and had been putting off the salary question hoping it would somehow resolve itself. What really stands out to me from all these responses is the consistency of the message: the IRS doesn't care whether you take distributions or not - if you're actively working in the business, you need reasonable compensation as an employee. The documentation aspect everyone mentions makes total sense too. I think the key insight for those of us in cash-tight growth phases is that "reasonable" doesn't necessarily mean "full market rate." It sounds like you can justify a lower salary based on business financial constraints, but it needs to be genuinely reasonable - not artificially low to dodge payroll taxes. For the OP's situation with $33k in profit after expenses, setting aside $25-30k for salary (as several people suggested) seems like a good balance between compliance and cash flow management. The remaining amount stays in the business for growth, and you can always increase the salary as revenue grows. Thanks to everyone who shared their real experiences - especially those who dealt with IRS audits or got professional guidance. This kind of practical advice is invaluable for navigating S-Corp compliance!

Just wanted to share my experience with this exact situation! I had multiple Roth IRA contributions throughout 2023 and then got hit with a surprise year-end bonus that pushed me over the income limit. The key thing I learned is that you absolutely need to act quickly - the deadline is firm. My broker (Schwab) was actually really helpful once I got to the right department. They have a specialized team that handles excess contribution returns and they did all the earnings calculations for me using the method described above. One thing that wasn't immediately clear to me: when you withdraw the excess contribution plus earnings, the contribution amount comes back to you tax-free (since it was post-tax money), but the earnings portion gets added to your taxable income for the year you receive the distribution. So make sure you're prepared for that tax hit! Also, if you're close to income limits in the future, definitely consider the backdoor Roth strategy mentioned by others. It's a bit more paperwork but saves you from this whole headache.

I went through this same situation last year with Fidelity! You're absolutely right that the calculation can be confusing, especially with multiple contributions. Here's what I learned from my experience: Fidelity does have a specific form called "Return of Excess Contribution" that you can find in their forms library online. When you call, ask specifically for the "retirement account excess contribution department" - they'll transfer you to specialists who handle this all the time and actually know the calculation methods. Regarding your question about tracking each contribution separately - you don't need to! The IRS allows you to use the account value immediately before your first contribution for the tax year as your starting point, then your current balance as the ending point. The formula you mentioned is correct. One important thing I discovered: if you're doing this for 2024 contributions, you have until your 2024 tax filing deadline (including extensions) to fix it without penalty. But don't wait - the earnings calculation keeps changing as your account value fluctuates. Also, just to echo what others said about the tax implications - the contribution itself comes back tax-free, but any earnings on the excess contribution will be taxable income in the year you receive the distribution. Fidelity will send you a 1099-R showing the earnings portion.