Did you end up getting your audit resolved successfully even with the unresponsive agent? I'm curious if I should just stick with them but be more aggressive about contacting management, or if I should try one of the other options people mentioned.

Yes, it did get resolved successfully, but only after I escalated to a supervisor who assigned me a new agent. The important thing is to act quickly - don't wait until the last minute hoping your current agent will suddenly become responsive. If you're only 9 days from deadline, I'd honestly consider one of the other options mentioned alongside escalating with TaxAudit. The peace of mind from knowing your audit response is being actively handled is worth it. At minimum, request an extension from the IRS (which one of the services might help with) to give yourself more breathing room. Don't let the deadline pass without taking action.

It really depends on the complexity of your audit and your comfort level with tax matters. Simple correspondence audits focusing on one or two items can often be handled yourself if you have good documentation. More complex audits involving multiple years, business income, or substantial amounts are riskier to handle alone. If you do go the DIY route, be extremely organized, respond only to what they're asking for (don't volunteer additional information), and consider requesting an extension if you need more time to gather documents. The IRS publication "Your Rights as a Taxpayer" is worth reading before responding.

Thanks for the advice. Mine is pretty simple - just questioning some education credits I claimed. I have all the tuition statements and receipts so maybe I'll try handling it myself first. If it gets complicated I can always get help later I guess.

For the support test, would the mortgage payment and utilities I pay count toward my support of him? And would his contribution just be whatever he spends on himself from his SS money? Still trying to understand how to calculate this properly.

The support calculation includes housing costs, so your mortgage payment and utilities would definitely count, but only for his portion. The IRS generally accepts dividing these costs evenly by the number of people in the household. So if it's just you and your dad, half of your housing costs would count as support you provide for him. For his contribution, you're right - it's whatever he spends from his SS on his own support (food, clothing, medical expenses, personal items, etc.). If he puts money in savings or spends it on non-support items, that doesn't count as him supporting himself.

That's a good point. The most common audit trigger for HoH is when the dependent doesn't properly indicate their status. Communication is key here!

Does the IRS ever pre-approve these kinds of deductions? I'm worried about claiming it then getting hit with penalties later.

The IRS doesn't offer pre-approvals for specific deductions before you file. They review after the fact if questions arise. The best protection is thorough documentation. This means doctor's letters clearly stating medical necessity, history of treatments for issues caused by the excess skin, and a clear connection between the gastric bypass and the need for skin removal. The better your documentation, the stronger your position if questioned later.

That's really helpful! Did you have any issues with the IRS questioning the deduction? And did you need to get specific CPT codes included in your documentation?

Would it be worth filing anyway just to establish the capital loss? I hear you can carry those forward to future tax years when you might have actual income.

That's actually a good question about carrying forward the loss. Technically, yes, you could file just to document the $6 capital loss and carry it forward to future tax years. The IRS allows you to carry forward capital losses indefinitely until they're used up. However, for such a small amount ($6), it's probably not worth the effort of filing just for that. The time spent preparing and filing a return would far outweigh any potential future tax benefit from such a small loss. If the loss were larger (say, hundreds or thousands of dollars), then it would make more sense to file and establish that carryforward.

The threshold for PayPal to issue a 1099-K for crypto in 2025 is $600 in total proceeds, so they probably won't send one for a single $500 transaction. But even if they did, the IRS matching system would see it was sold at a LOSS, not a gain. They generally don't pursue non-filers when there's no tax due (especially for dependent students). Just keep your records showing it was a loss transaction.

I used Google Sheets for my first year in business and it was fine, but I only had about 10-15 transactions per month. I created columns for date, vendor, amount, category, and notes. Then had another sheet that totaled each category for tax purposes. Worked okay, but got tedious to maintain as I grew.