Reading through all these experiences has been sobering. I came here initially skeptical but open-minded about creative tax strategies, but the consistent pattern of audit failures and financial consequences is impossible to ignore. What strikes me most is how these schemes prey on people's desire to minimize taxes through what appears to be "sophisticated" planning. The volcanic ash arrangement has all the classic red flags: inflated valuations, promoters focused on tax benefits rather than economic returns, and the fundamental question of why anyone would donate something rather than sell it at the claimed fair market value. I'm particularly grateful for the insights from tax professionals who've seen these cases play out over years. The extended audit timeline, compounding penalties and interest, and the reality that promoters disappear when the IRS comes calling paint a clear picture of why these arrangements are so risky. For anyone considering similar schemes, the advice here is unanimous: legitimate tax planning should make economic sense independent of tax benefits. If the primary selling point is the tax deduction rather than the underlying investment merit, that's your red flag to walk away. I'll be sticking with conventional retirement contributions, legitimate business deductions, and actual charitable giving to causes I care about. Sometimes the boring approach really is the wise approach when it comes to taxes.

I've been lurking in this community for a while but felt compelled to create an account just to add my voice to this discussion. As a forensic accountant who's worked on several IRS enforcement cases involving these exact types of schemes, I can confirm everything that's been shared here is spot-on. The volcanic ash arrangement you're describing follows the same playbook I've seen in conservation easements, artwork donations, and patent charity schemes. The IRS has become incredibly sophisticated at identifying these patterns - they use data mining to flag returns with similar charitable deduction amounts, asset types, and even common promoter language in supporting documentation. What many people don't realize is that when the IRS audits these arrangements, they don't just look at your individual return. They audit the entire syndicate - sometimes hundreds of taxpayers who participated in the same scheme. This creates a massive database of evidence that makes it nearly impossible for anyone to successfully defend the deductions. I've personally worked on cases where the penalties and interest exceeded the original tax "savings" by 3:1 ratios. The financial and emotional toll on families is devastating, especially when they realize the promoters have structured their businesses to be judgment-proof when the inevitable lawsuits start flying. Trust your gut on this one - if it sounds too good to be true, it absolutely is. The IRS didn't get fooled by these schemes when they were new, and they certainly won't now that they've had years to perfect their enforcement strategies.

As someone who works in payroll, I can tell you this happens more often than it should. The Box 13 retirement plan checkbox is sometimes overlooked because it's separate from the actual contribution amounts in Box 12. Our software is supposed to automatically check this box when there are retirement contributions, but sometimes during year-end processing things get messed up. Definitely ask for a corrected W-2, but know that this particular error won't affect your tax calculation or refund amount. The IRS systems primarily look at the Box 12 codes (D, AA, etc.) to verify retirement contributions, not the Box 13 checkbox.

Don't make this more complicated than it needs to be. Your 401k contributions are correctly showing in boxes 12-D and 12-AA, which is what actually matters for tax calculations. The Box 13 checkbox is primarily used to determine eligibility for deducting traditional IRA contributions. If you're not contributing to a traditional IRA, this has zero impact on your taxes. Even if you are, the IRS can see your 401k participation from the Box 12 entries. I've had this happen twice and just filed my taxes normally - never heard a peep from the IRS about it.

Just my experience, but I deducted my hearing aids last year as a medical expense along with some dental work and surgery costs. The combined amount got me over the 7.5% threshold. When you file, make sure you keep all receipts and documentation from your audiologist about the medical necessity. I also got a letter from my doctor explaining why I needed them, which helped support the deduction.

It's not too complicated to itemize, especially if you have substantial medical expenses like hearing aids. You'll use Schedule A instead of taking the standard deduction. The key is making sure your total itemized deductions (medical expenses over 7.5% of AGI, state/local taxes, mortgage interest, charitable donations) exceed the standard deduction amount to make it worthwhile. For 2024, the standard deduction is $14,600 for single filers and $29,200 for married filing jointly. If your hearing aids plus other medical expenses get you over that 7.5% AGI threshold and your total itemized deductions beat the standard deduction, then it's worth doing. Most tax software will automatically calculate both scenarios and tell you which saves you more money.

Just wanted to add my experience for anyone else in a similar situation. I had almost the exact same scenario last year - bought Bitcoin through CashApp in 2021 and sold at a small loss in 2024. Never received a 1099-B from them, but I went ahead and filed using my transaction records from the app. The key thing I learned is that you can actually download a CSV file of all your Bitcoin transactions directly from CashApp. Go to your profile, then "Privacy & Security," then "Download My Data." It takes a day or two to process, but you get a comprehensive file with all transaction details including dates, amounts, and fees. This makes filling out Form 8949 much easier than trying to screenshot individual transactions. Also, don't forget to include any fees CashApp charged in your cost basis - those small transaction fees can add up and increase your deductible loss. In my case, the fees actually made my loss about $15 higher than I initially calculated, which helped a bit more with the tax offset. The IRS accepted my return without any issues, and I got my refund on schedule. So definitely don't wait around for forms that probably aren't coming!

I went through something very similar last year! Based on your transaction amounts ($950 purchase, $920 sale), CashApp definitely won't be sending you a 1099-B since you're well under the $600 reporting threshold that others mentioned. Here's what I'd recommend: Don't wait any longer to file your taxes. You have everything you need right in the CashApp app. Go to your Bitcoin transaction history and document the purchase date (2021), purchase amount ($950), sale date (last month), and sale amount ($920). Since you held for over a year, this is a long-term capital loss of about $30. Even though $30 might seem small, it's still a legitimate deduction that can offset other income. Plus, if you're waiting for your refund, there's really no benefit to delaying your filing when you already have all the information you need. The IRS doesn't require you to have the 1099-B to report crypto transactions - you just need accurate records, which you can get directly from CashApp. I filed without waiting for forms and had zero issues with my return being processed.

Thanks for starting this discussion - this is such an important topic that many people don't think about until it's too late! I'm dealing with a similar situation where I converted my primary residence to a rental for a few years and now I'm back living in it. One thing I want to emphasize is that the IRS computer systems have become incredibly sophisticated at matching data. When you eventually sell, they'll receive a 1099-S showing the sale price, and their systems can cross-reference that against your historical Schedule E filings to look for potential depreciation recapture situations. The key thing to remember is that depreciation recapture is calculated on the LESSER of: (1) the total depreciation you claimed (or should have claimed) during the rental period, or (2) the gain on the sale. So even if your property appreciates significantly by 2035, you're only paying recapture tax on that 2.5 years worth of depreciation, not the entire gain. My advice would be to create a simple spreadsheet now documenting your rental period dates, the property's basis when converted to rental, and the annual depreciation amounts. Even if you lose your tax returns, having this basic information will help you (or your tax preparer) reconstruct the numbers accurately when the time comes. The peace of mind is worth the small effort now!

This is such a valuable discussion! As someone who works in tax compliance, I want to add a few practical points that might help with your long-term planning. First, regarding IRS record keeping - while they officially keep records for about 7 years, their property transaction matching systems have become much more sophisticated. They maintain databases that can cross-reference 1099-S forms (property sales) with historical Schedule E filings going back much further than 7 years. So yes, they absolutely can and do catch depreciation recapture issues even from many years ago. One thing I haven't seen mentioned yet is the Section 121 exclusion interaction. Since this was your primary residence before and after the rental period, you may be able to exclude up to $250K (single) or $500K (married) of gain when you sell - but this doesn't apply to the depreciation recapture portion. That will always be taxable at the 25% rate (under current law). My recommendation would be to treat this as a compliance issue, not a "will they catch me" gamble. Create that documentation spreadsheet others have mentioned, but also consider filing Form 3115 (Application for Change in Accounting Method) if you realize you calculated depreciation incorrectly in those years. This lets you fix errors proactively and often reduces penalties. The peace of mind of having everything properly documented and calculated is worth far more than any potential tax savings from hoping it gets overlooked.