Can I write off my work accident expenses and medical costs as a 1099 truck driver?

Do you need to notify your insurance company even if you handled it privately? And for the medical expenses, wouldn't it be better to claim them as business expenses rather than personal medical expenses since the 7.5% threshold is pretty high?

You generally don't need to notify your insurance if you've resolved the accident privately, though some policies do require reporting all accidents regardless of claims. It's always best to check your specific policy language to be certain. Regarding the medical expenses, you're absolutely right that in most cases, deducting them as business expenses on Schedule C would be more advantageous than claiming them as itemized medical expenses. The 7.5% AGI threshold often makes it difficult to get much benefit from medical expense deductions. Since the injury occurred while performing work duties, there's a good case for treating these as ordinary and necessary business expenses.

Does it actually work with 1099 situations specifically? I've tried other tax tools but they seem to struggle with independent contractor stuff.

I'm a little skeptical about AI tools. How accurate is it really? I'd hate to get audited because some robot told me I could write something off when I actually couldn't.

It definitely works great with 1099 situations. I'm independent as well, and it has specific categories for business expenses related to independent contractors. It even explained to me how to properly categorize things like per diem vs actual expenses for meals on the road. Regarding accuracy, I was skeptical too at first, but it cites the specific IRS regulations that apply to each deduction. My accountant actually reviewed everything after I used it and said it was spot on. The tool doesn't just say "yes this is deductible" - it explains why and gives you the documentation to back it up if you ever get questioned.

Wait, this is actually a thing? How much does it cost? I've literally spent HOURS trying to get through to the IRS before.

Sounds too good to be true. I've tried calling the IRS multiple times and just gave up. They never answer. How can this service magically get through when nobody else can?

They don't publish their rates on their website, but when I used it, the cost was very reasonable compared to the time I saved. Think about what your time is worth per hour - for me it was definitely worth it. You only pay if they actually get someone on the line for you. The way it works is they have a system that constantly redials and navigates the IRS phone tree until they get through to someone. It's not magic - just technology and persistence. They basically do the waiting for you, and then when they get a human, they call you and connect you directly. I was skeptical too until I tried it and was talking to an actual IRS agent within about an hour of signing up (after trying unsuccessfully for days on my own).

Thanks for this info. Did your accountant have you include any specific documentation with your tax return or did you just keep the receipts in case of an audit? And did you have to explain the circumstances anywhere on the actual return?

I just kept all receipts and the agreement with the homeowner in my files - didn't submit them with the return. My accountant did add a brief note in the description field for the "other business expenses" line that said "work-related injury medical costs" but nothing detailed. If you use tax software, there's usually a field for descriptions where you can briefly note what the expense was for. The key is having your documentation organized and ready if they ever ask about it. I keep a dedicated folder for each tax year with all my receipts and any unusual expense documentation.

This is good advice. I learned this the hard way too. Got a proper occupational policy after paying out of pocket for a back injury. The monthly premium is tax deductible too!