quick questions - do the payments actually need to match the profitability by quarter or can i just divide my total estimated taxes for the year into 4 equal payments? my s-corp has really seasonal income so some quarters have way more profit than others.

Great question about S Corp quarterly payments! Just to add some clarity - you're absolutely right to be thinking about this carefully. The key thing to remember is that as an S Corp owner, you wear two hats: employee (if you take a salary) and owner/shareholder. From the business account, you should pay: - Payroll taxes for your salary (employer portion of FICA, unemployment taxes, etc.) - Any business-specific taxes like state franchise fees From your personal account, you should pay: - Estimated quarterly payments for the income tax on your share of the S Corp profits - Your portion of self-employment tax equivalent (though S Corp profits aren't subject to SE tax, which is one of the benefits) Since this is your first profitable quarter, make sure you're also paying yourself a reasonable salary if you haven't been already - the IRS expects S Corp owner-employees to take W-2 wages before distributions. Congrats on the profit, and keep that business/personal separation clean for your records!

I went through a very similar situation last year with my S-corp and COBRA premiums. The key thing that helped me was getting everything documented properly from the start. Here's what I learned: Yes, you can absolutely deduct the full $39,000 in COBRA premiums as a self-employed health insurance deduction, but the process matters. Your S-corp needs to reimburse you for those premiums you paid out of pocket (make sure this happens before December 31st). The reimbursement gets added to your W-2 income in Box 1 but not Boxes 3 and 5. For documentation, I created a simple board resolution stating that the company would reimburse health insurance premiums for employees. I kept copies of all my COBRA payment receipts, the reimbursement check from my business account, and a memo explaining the reimbursement. My CPA said this was more than sufficient. The amount might seem large, but it's a legitimate business expense. I claimed about $32,000 last year with no issues. Just make sure your accountant codes everything correctly on your W-2 and that you claim the deduction on Schedule 1 of your 1040, not as an itemized medical expense. One tip: If you're switching to ACA coverage when COBRA ends, you can handle those premiums the same way going forward.

This is exactly the situation I was in two years ago! The confusion you're experiencing is totally understandable because the rules for S-corp owners are different from sole proprietors, and not all tax professionals are familiar with the specifics. You're absolutely right that you can take the full deduction for your COBRA premiums. The process everyone outlined above is correct - have your S-corp reimburse you for the $39,000 you paid out of pocket, include it in your W-2 Box 1 income (but not FICA wages), then claim the self-employed health insurance deduction on your personal return. One thing I'd add that helped me sleep better at night: I also kept a spreadsheet tracking each monthly COBRA payment with dates, amounts, and confirmation numbers. When my S-corp reimbursed me, I referenced this spreadsheet in the memo line of the reimbursement check. It created a clear paper trail showing the business purpose of the reimbursement. The second accountant who told you COBRA doesn't qualify was simply wrong - there's no distinction in the tax code between regular health insurance and COBRA continuation coverage for this deduction. Don't let that bad advice cost you thousands in legitimate tax savings! Make sure to get this reimbursement processed before December 31st, and you'll be in great shape for your 2024 taxes.

18 Random but related tip - if you're fronting expenses and getting reimbursed later, use a good rewards credit card! I put about $9k of company expenses on my card last year and earned enough points for a round-trip flight. Company gets their supplies, I get reimbursed fully, AND I get travel rewards. Triple win!

Great question! You're absolutely right to be organized with your documentation - that's key. Since you're getting fully reimbursed through your company's expense report system, you don't need to report these transactions on your personal tax return at all. This falls under what the IRS calls an "accountable plan" since you're providing receipts, documenting business purposes, and getting reimbursed for actual expenses. The company treats these as their business expenses, and from your perspective, it's like they paid the vendors directly - you were just the middleman. The fact that you temporarily used your personal credit card doesn't change the tax treatment. No need to report the $4-5k in purchases as deductions, and the reimbursements aren't considered income to you. Keep doing what you're doing with the documentation though - those records are important if you ever need to prove the business connection of the expenses.

Random question - does anyone know if guaranteed payments from an LLC taxed as a partnership qualify for QBI? I've heard conflicting things.

This is such a helpful thread! I'm in a similar situation with my single-member LLC and have been stressing about getting the QBI calculation right. One thing I want to add that might help others - make sure you're using the correct SE tax amount in your calculation. The "50% of SE tax" that gets deducted from your QBI should match exactly what you deduct on Form 1040 line 15 (the deductible portion of self-employment tax). I made the mistake of using 50% of my total SE tax liability instead of the actual deductible portion, which threw off my entire QBI calculation. The deductible portion is slightly less than 50% due to how SE tax is calculated. Also, for anyone using tax software, double-check that your health insurance premiums are properly coded as self-employed health insurance. If they're mistakenly categorized as a business expense on Schedule C, you could be double-deducting them in your QBI calculation.

Another option that worked for me when I was missing old W2s - check if you have any old bank statements or pay stubs from 2017. Even if you don't have the actual W2s, having pay stubs can help you verify the information on the IRS wage transcript when you get it. I found some old pay stubs in a random folder that helped me confirm the numbers matched up correctly. Also, if you used any tax software like TurboTax or H&R Block in previous years (even if you didn't finish filing), they sometimes keep your partially completed returns in their systems. Worth logging into any old accounts you might have had to see if there's any 2017 data saved there. It's a long shot but could save you some time! One more thing - when you do get your wage transcript from the IRS, double-check that it includes ALL your employers from 2017. Sometimes if a company didn't report properly, their info might not show up on the transcript, and you'd need to track that down separately.

One more resource that might be helpful - if you're feeling overwhelmed by all the different options people have mentioned here, the IRS actually has a pretty good online tool called the "Interactive Tax Assistant" that can walk you through exactly what you need to do for your specific situation. You can find it on irs.gov and it asks you questions about your circumstances (like missing W2s, unfiled returns, etc.) and gives you personalized guidance. Also, since you mentioned this is for 2017, just be aware that if you end up owing taxes, the penalties and interest will have been accumulating all this time. But don't let that scare you off from filing - the penalties for not filing are way worse than the penalties for filing late but paying late. The sooner you get this sorted, the better. And like others mentioned, you might qualify for penalty relief if this is your first time having issues with the IRS. Good luck getting everything sorted out! It sounds like you have some solid options to work with now.