Has anyone else heard that there's a special rule if your business is an S-corp instead of a sole proprietor? My accountant told me S-corp owners can avoid this issue completely. Something about the health insurance being a reimbursed expense instead of a deduction. Thinking about changing my business structure next year if it'll save me on self employment taxes.

Logan, you're absolutely right and your brother is wrong. As someone who's been self-employed for over 8 years, I can confirm that health insurance premiums do NOT reduce your self-employment tax liability. You'll pay the full 15.3% SE tax on your entire net profit from Schedule C, then get to deduct the health insurance premiums later on Form 1040 Schedule 1. This is one of the most common misconceptions about self-employment taxes. The health insurance deduction is what's called an "above-the-line" deduction that reduces your adjusted gross income for regular income tax purposes, but it happens after SE tax is calculated. So in your case with $750/month ($9,000/year) in premiums, you'll still pay SE tax on your full 1099 income, but you'll save on income tax by deducting those premiums. It's frustrating because it feels like it should be a business expense, but the IRS treats it as a personal deduction with special rules for self-employed folks. Show your brother IRS Publication 535 - it clearly states that health insurance premiums are not deductible as business expenses on Schedule C. You can find it on the IRS website. Good luck settling that family argument!

I'm going through the exact same nightmare! Filed on February 22nd and have been stuck on "received" for over 5 weeks now. This thread has been incredibly eye-opening - I had no idea about services like taxr.ai or that creating an online IRS account could reveal notices that don't show up in the regular refund tracker. What's particularly maddening is that my return is about as simple as it gets - single filer, one W-2, standard deduction, no dependents or credits. Yet here I am in the same boat as everyone else with these massive delays. The stories about tiny discrepancies in employer reporting causing weeks of delays are honestly mind-blowing. How are we supposed to know if our employer reported our health insurance premiums with a $20 difference? After reading all these success stories, I'm definitely going to create an IRS online account today to check for any hidden notices. If that doesn't reveal anything, I'll try taxr.ai to see if there are any data mismatches I'm unaware of. At this point, I'd rather spend a little money to identify the problem than continue this endless cycle of checking the website multiple times a day and getting more frustrated. Thanks to everyone for sharing your experiences and solutions - it's both comforting and helpful to know this is a widespread issue affecting so many people with similar timelines. Hopefully we'll all see some movement soon!

I'm dealing with the exact same frustrating situation! Filed my return on February 16th and have been stuck on "received" status for over 6 weeks now. Like so many others here, I've been compulsively checking the "Where's My Refund" tool multiple times daily, which is definitely not helping my stress levels. This thread has been incredibly helpful and reassuring - I had no idea that this was such a widespread issue this filing season. My return is also pretty straightforward (W-2 income, standard deduction, student loan interest), so I was really confused about why it was taking so long when friends who filed later already got their refunds. The stories about tiny discrepancies in employer reporting causing major delays are really eye-opening. I never would have thought that a small difference in health insurance reporting or withholding amounts could hold up a refund for weeks. It makes me wonder if there's some small mismatch in my return that I have no way of knowing about. Based on all the success stories shared here, I'm going to create an IRS online account first to check for any notices that might not show up in the refund tracker. If that doesn't reveal anything, I'll definitely look into taxr.ai to see if it can identify any potential issues with my return. At this point, I'd rather be proactive and possibly spend a small amount to figure out what's going on than continue this endless waiting game. Thanks to everyone for sharing their experiences and solutions - it's both comforting and helpful to know I'm not alone in this!

Has anyone mentioned the substantial contribution rules yet? If your LLC is making donations worth more than $5,000, you'll need a qualified appraisal for non-cash donations. And for donations over $500, you need to file Form 8283 with your tax return. Also, the rules are different depending on how your LLC is taxed. If it's a single-member LLC treated as a disregarded entity, the donation is treated as coming from you personally. If it's taxed as a partnership or S-corp, the deduction passes through to your personal return but with different limitations. This is definitely not a DIY situation - get a good tax professional who understands both business taxation and non-profit rules.

I've been following this discussion with great interest as someone who's navigated similar waters. One critical aspect I haven't seen fully addressed is the potential for excess benefit transactions under IRC Section 4958. When you're the founder/controller of both the LLC and the non-profit, the IRS may view you as a "disqualified person" under the intermediate sanctions rules. This means any transaction between your entities must provide no more than reasonable compensation or fair market value to avoid penalty taxes. The $120K in "donations" you're describing could be scrutinized not just as potentially inflated charitable deductions, but as excess benefits flowing to you indirectly through your non-profit. The IRS might argue that you're effectively paying yourself through the non-profit while claiming tax deductions through the LLC. A few key points to consider: - Document fair market value for any goods/services transferred - Ensure your non-profit's board (if you have independent members) formally approves accepting these contributions - Consider whether some of these expenses might be better classified as program-related investments rather than donations - Be prepared to demonstrate that the non-profit is serving a genuine charitable purpose beyond just providing you tax benefits Given the complexity and audit risk, I'd strongly recommend getting an opinion from a tax attorney who specializes in exempt organizations, not just a general CPA.

I'm a bit confused about one thing - if I did have a funded Robinhood account with some activity, what tax software is best for handling investment stuff? I've only ever used the free version of TaxAct for my super simple returns, but I'm planning to start investing this year.

Emma, you're absolutely right not to worry about tax forms from Robinhood in your situation. Since you never funded the account or made any trades, there's zero taxable activity to report. Robinhood only generates 1099 forms when there's actual financial activity - like stock sales, dividends received, or interest earned on cash balances. Just creating an account doesn't trigger any tax reporting requirements. You won't receive any forms from them, and there's nothing you need to include on your tax return related to this account. It's essentially like signing up for any other app - no tax implications until you actually start using it for financial transactions. If you do decide to start investing in the future, that's when you'd need to pay attention to the tax documents they send. But for now, you can cross this worry off your list completely!

Has anyone had experience with how state taxes work with dual-status federal returns? I'm in a similar situation but also worried about state filing requirements. California seems particularly aggressive about taxing people with any connection to the state.

I went through a very similar situation last year and can confirm you'll need to file as dual-status. The IRS is pretty strict about this - if you change residency status during the tax year, dual-status filing is mandatory regardless of how simple your income situation might seem. For your capital gains, since you sold the stocks while physically present in the US (before May 2025), they'll be reported on the Form 1040 portion of your return, not the 1040NR. This is because the US has taxing rights on capital gains realized while you were a US resident for tax purposes. One thing to watch out for - make sure you're calculating your exact residency termination date correctly using the substantial presence test. It might not be exactly when you physically left in May, depending on your presence history in prior years. The IRS has specific rules about this that can affect which form certain income items go on. I ended up hiring a CPA who specializes in international tax because the dual-status rules are genuinely complex, but I know that's not always budget-friendly. If you do go the DIY route, make sure to attach a statement to your return explaining the dual-status filing and clearly marking which periods each form covers.