I'm dealing with something similar right now with my food truck business. Been operating for 2 years and just found out I should have been collecting sales tax on prepared food in my state. The panic is real! One thing I learned is that you definitely want to get registered for a sales tax permit ASAP even before you figure out the back taxes situation. Continuing to operate without one while you're sorting out the past issues just makes things worse. Also, keep detailed records of EVERYTHING moving forward - sales by location, exempt vs taxable items, etc. I started using a POS system that automatically calculates and tracks sales tax by jurisdiction since I operate in multiple cities. It's been a lifesaver for staying compliant going forward while I work through my past issues. The voluntary disclosure route really does seem to be the way to go based on what I'm reading here. Better to rip the band-aid off and deal with it head-on than live in constant fear of getting caught.

As someone who went through a similar nightmare with my consulting business, I can't stress enough how important it is to act quickly but thoughtfully. I made the mistake of panicking and calling my state tax office without proper preparation, which actually hurt my case initially. Here's what I wish I had done from day one: First, stop beating yourself up - this happens to thousands of small business owners every year. Second, immediately start collecting sales tax going forward to prevent the problem from getting worse. Third, gather ALL your sales records systematically before contacting anyone. The key thing that saved me was documenting everything chronologically and being able to show the state that this was genuinely an oversight, not intentional tax evasion. I had to provide bank statements, marketplace records, invoices - everything that showed my sales history. The more organized and transparent you are, the better your chances of getting into a voluntary disclosure program with reduced penalties. One last tip: don't try to handle this alone if your total liability is significant. A tax professional who specializes in sales tax compliance can often save you more money in reduced penalties than their fees cost. They know exactly how to present your case to maximize your chances of penalty relief.

Has anyone actually tried to submit an amendment past the 3 years just to see what happens? I'm curious if they automatically reject it or if there's some review process where they might consider special circumstances.

I'm sorry to say this, but based on everything discussed here, your mother is unfortunately outside the refund window for her 2018 medical expenses. The 3-year statute ran out in April 2022 (assuming she filed by the original due date in 2019). However, don't give up entirely on tax savings! A few things to consider: 1. **Future planning**: Make sure you're tracking all her ongoing medical expenses for current and future tax years. If she's still having significant medical costs, you don't want to miss them again. 2. **State taxes**: Some states have different amendment periods than federal. It might be worth checking if your state allows longer amendment windows. 3. **Other missed deductions**: While you're reviewing her situation, check if there are any other deductions or credits from more recent years (2021-2024) that might have been missed and are still within the amendment window. The $12K potential refund stings, but unfortunately the IRS is extremely rigid about these deadlines. Even filing the amendment now would likely just result in a rejection letter citing the statute of limitations. Better to focus that energy on making sure nothing gets missed going forward.

I inherited a nonqualified annuity last year too, and my situation was slightly different. My tax preparer said I absolutely needed the 1099-R to properly file, even though taxes were withheld. Has anyone used H&R Block or TurboTax for this kind of situation? I'm trying to figure out which would handle this better.

I'm dealing with a very similar situation with my grandmother's nonqualified annuity that I inherited last year. The missing 1099-R is definitely a red flag - I received mine from the insurance company even though they withheld the correct amount of taxes. Here's what I learned from my tax preparer: even if the annuity company calculated and withheld taxes correctly, you still need to report the distribution on your tax return. The 1099-R shows the IRS that you properly accounted for the income and any withholding. I'd strongly recommend calling Nationwide again and asking specifically for the tax reporting department. When I had issues getting my 1099-R, I had to escalate beyond the general customer service reps. They should be able to reissue it or at least explain in writing why one wasn't generated. Don't spend that money you set aside until you get this resolved - better safe than sorry when it comes to the IRS. The fact that taxes were withheld is good, but without proper documentation, you could run into issues during filing or if audited later.

Did you check box A, B, C, D, or E on the form? If you're claiming any of the special conditions for waiver (like I had to when I had an unexpected wealth event mid-year), you need to attach an explanation letter along with the form. The IRS was super picky about having that documentation when I filed my 2210.

Based on everyone's responses, it sounds like the most likely issue is that you need to use 110% of your 2022 tax liability for line 5 since your AGI was over $150,000. But before you resubmit, I'd suggest double-checking a few things: 1. Make sure you're looking at the actual tax amount from line 16 of your 2022 Form 1040 (not line 24 which includes additional taxes) 2. Calculate both 90% of your 2023 tax ($13,423.50) AND 110% of your 2022 tax, then use whichever is smaller 3. If you haven't already, consider whether any of the waiver conditions apply to your situation (boxes A-E on the form) The good news is that once you get the calculation right, the IRS should process your refund relatively quickly. I went through something similar last year and it was frustrating, but getting that line 5 calculation correct based on your income level should resolve the issue.

Has anyone successfully gotten a refund from Sprintax when they mess up calculations like this? I paid $75 for them to prepare my return last year and found out later they calculated my substantial presence completely wrong. I ended up having to file an amended return which cost me even more money.

I went through almost the exact same situation last year! After spending hours trying to figure out why Sprintax was calculating my substantial presence test incorrectly, I realized the issue was in how I had entered my visa transition dates. Like you, I'm on F-1 status, and I had entered my initial arrival date correctly but made an error with when my 5-year exemption period actually started. It turns out the exemption is based on calendar years, not the actual date you first arrived. So if you first came to the US in September 2019, your first exempt calendar year was still 2019, making 2024 potentially your 6th calendar year (and therefore not exempt). I'd recommend double-checking not just your entry/exit dates, but specifically verifying when your F-1 exemption period began and ended. In my case, once I corrected this in Sprintax, the substantial presence calculation matched my manual calculation perfectly. If you're still having trouble after checking this, definitely reach out to their support with screenshots. They were actually pretty helpful once I could show them exactly where the discrepancy was occurring.