That's interesting. I didn't have any extreme circumstances like that though. Just poor planning and procrastination on my part unfortunately. Do you know if the IRS ever just "forgives" these situations if I explain it was an honest mistake?

The IRS generally doesn't "forgive" missed deadlines just because it was an honest mistake. They hear that all the time. If it was truly just procrastination, you'll need to follow the pay-first-then-claim-refund route the others mentioned. However, there was actually a recent Supreme Court case (Boechler v. Commissioner) that established equitable tolling could apply for certain tax deadlines, though that was for Collection Due Process cases, not deficiency notices. Still, tax law continues to evolve on these issues.

In my experience, amended returns are taking FOREVER right now - like 6+ months. I filed one in April and it's still "processing" according to Where's My Amended Return tool. But that's separate from the Tax Court deadline issue. The amended return won't stop the deficiency assessment if you missed the petition deadline.

They actually did send me a 1099-MISC for the entire settlement amount of $78,000! I was panicking thinking I'd have to pay taxes on all of it. How do I correct this when the insurance company reported the full amount to the IRS?

Don't worry - this happens all the time with settlement payments. Even though the insurance company reported the full amount on the 1099-MISC, you don't need to report the entire amount as taxable income on your return. You'll need to file Form 8275 (Disclosure Statement) with your tax return to explain the discrepancy. On this form, you'll explain that the 1099-MISC includes non-taxable compensation for physical injuries under Section 104(a)(2) as well as the attorney fees that should be allocated proportionally. This way, the IRS will understand why your reported income doesn't match the 1099-MISC amount. Just be sure to keep all your settlement documentation in case of questions later. Many tax software programs like TurboTax have sections specifically for handling this situation.

In multi-year settlements, you generally allocate the attorney fees based on when you receive the income. So if the fees were all paid from last year's portion, but they relate to the entire settlement, you should allocate the fees proportionally across the years of payment.

That makes sense, thank you! So I should figure out what percentage of my total settlement I received last year, and then deduct that same percentage of the total attorney fees on last year's return. Then I'll deduct the remaining portion of fees on this year's return when I report the second payment. That's clearer than anything my attorney explained!

Is there an easy way to separate these out? My property tax bill has the base amount plus like 4 different "special assessments" for things like schools and flood control. Are those considered part of the deductible property tax?

Generally, special assessments for schools, flood control, and similar public improvements are deductible as property taxes as long as they're based on the assessed value of your property and apply to all properties in the jurisdiction. However, special assessments for local benefits that increase the value of your property (like sidewalks, streets, or water/sewer lines specifically for your neighborhood) are not deductible as taxes. The easiest way to separate these is to look at your property tax statement - it should itemize the different charges. If you're using tax software, it will usually ask you to enter only the deductible portions. Or if you work with a tax professional, they'll know how to properly categorize each item.

It really depends on your total itemized deductions. Remember that itemizing includes property taxes, state/local income taxes (capped together at $10k), mortgage interest, charitable contributions, and some medical expenses. If all those combined exceed your standard deduction, then itemizing is worth it. But you're right that the higher standard deduction has made itemizing less beneficial for many homeowners.

Thanks for bringing this up - I hadn't considered the statute of limitations angle. Do you think filing the Form 8606 now for those old contributions might trigger some kind of review of those past tax years?

Filing Form 8606 now for old contributions typically doesn't automatically trigger an audit, but it does put those years on the IRS's radar. The good news is that you're trying to comply with the rules by properly documenting your basis in the IRA, which looks better than if they discovered the unreported contributions some other way. The key is documentation - make sure you have records of all those contributions and be prepared to show they were made with after-tax dollars. If you're concerned, working with a tax professional who specializes in IRA issues might be worth the investment to ensure everything is handled properly and to help respond if the IRS does have questions.

This is incorrect information. The Tax Cuts and Jobs Act eliminated the deduction for IRA losses completely through 2025. Even before that, claiming such losses was extremely difficult and rarely beneficial due to the AGI limitations. Please don't give tax advice if you're not certain - it could cause serious problems for the OP.

Thanks for bringing up the look-back rule - I hadn't considered that! I do have a small 1231 loss from a property I sold in 2023. So if I understand correctly, a portion of my current gain would be considered ordinary income rather than capital gain? Would that portion not be eligible for OZ investment?

Yes, exactly. If you had a 1231 loss in 2023, a portion of your current 1231 gain would be recaptured as ordinary income to the extent of that previous loss. That recaptured portion would not be eligible for OZ investment, since OZ investments can only be made with capital gains. For example, if you had a $10,000 1231 loss in 2023 and now have a $50,000 1231 gain, $10,000 of your current gain would be treated as ordinary income and only the remaining $40,000 would be treated as capital gain eligible for OZ investment.

I invested in an OZ fund after selling a small apartment building in 2022. The fees are definitely higher than typical investment funds, but remember you're getting tax benefits that can offset those costs. I went with a fund focused on multifamily development in emerging markets which aligned with my investment goals. Make sure you do due diligence on the fund manager's track record and understand the timeline - you need to hold for 10+ years to get the full tax benefits on appreciation. And be prepared for the tax bill in 2026 on your initial deferred gain.