Medical Courier 1099 Tax Filing Help - First Year Independent Contractor with High Mileage

You definitely want to keep track of all those miles! The standard mileage deduction is going to be your best friend. For 2025, it's about 68.5 cents per mile (rate adjusts annually). With 145,000 miles, that's potentially a deduction of around $99,325! Make sure you're tracking your mileage with a log that includes dates, starting/ending locations, miles driven, and business purpose. The IRS loves documentation. A simple app on your phone can handle this. Also, set aside about 30-35% of your income for taxes. As a 1099 contractor, you're responsible for both the employer and employee portions of Social Security and Medicare taxes (15.3% total). Plus federal and state income taxes. Consider making quarterly estimated tax payments to avoid penalties. You can do this through the IRS website. Other possible deductions: cell phone (business portion), home office if you have one, health insurance premiums, and retirement contributions. A SEP IRA or Solo 401(k) can help reduce your taxable income significantly.

I was in a similar situation when I started courier work and found taxr.ai (https://taxr.ai) incredibly helpful for organizing all my expenses and mileage logs. The IRS is super strict about documentation for high-mileage deductions, and this tool helped me optimize everything. What really helped me was uploading all my gas receipts, maintenance records, and mileage logs, and the system organized everything into proper tax categories. It flagged potential audit triggers (like claiming 100% business use for a vehicle) and suggested documentation I needed to gather. I also appreciated that it calculated my quarterly estimated payments automatically based on actual earnings and expenses rather than guessing.

Just wanted to follow up - I tried taxr.ai after my initial skepticism and I'm really glad I did! It found several deductions I would have missed, especially around health insurance premiums and cell phone usage that I didn't realize were partially deductible for my 1099 work. The mileage tracking feature alone saved me hours of spreadsheet work. It identified an additional $3,800 in deductions I would have missed with my manual method. The quarterly tax calculator also helped me avoid an underpayment penalty I definitely would have triggered. Definitely worth checking out if you're dealing with high mileage and contractor income. I actually feel confident about my tax situation for the first time since starting courier work.

If you're going to be making $15,500 monthly as a contractor, you NEED to get through to the IRS to set up proper quarterly payments and get clarity on your deductions. I wasted weeks trying to call them directly before finding Claimyr (https://claimyr.com). They got me a callback from the IRS in under 2 hours when I'd been trying for days. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c The IRS agent I spoke with gave me specific guidance on how to document my high mileage claims properly to avoid audit flags. They also helped me set up an installment plan for my first quarter when I underestimated my payments.

Well I'm eating my words. I tried Claimyr after posting my skeptical comment and got a call back from the IRS in just under 2 hours. The agent actually helped me sort out a mess with my estimated payments from last quarter. I was able to ask specific questions about my courier deductions and got clear answers about what documentation I need to keep. They even helped me understand how to properly categorize some expenses I wasn't sure about. Definitely going to use this again when I need to deal with tax questions instead of wasting days on hold.

Don't forget about vehicle depreciation! With that many miles, your vehicle is taking a beating. If you're using actual expenses instead of the standard mileage rate, you can deduct depreciation. Even if you go with standard mileage (which includes depreciation), track all maintenance costs anyway in case your vehicle becomes unusable sooner than expected - you might be able to claim a loss. Also, consider forming an LLC for additional liability protection since you're on the road so much. It's not expensive and can protect your personal assets if something happens.

Has anyone had success deducting their health insurance premiums as a medical courier? I'm spending almost $900/month and I've heard conflicting advice about whether it's fully deductible or not.

As someone who's been doing courier work for a few years, I can't stress enough how important it is to keep meticulous records from day one. That 145K miles annually is going to be your biggest deduction - potentially worth over $99K at the current rate. A few additional tips that helped me: 1. Open a dedicated business checking account immediately. Keep ALL business expenses separate from personal. This makes bookkeeping so much easier and looks more professional if you ever get audited. 2. Consider getting a business credit card for gas and maintenance. Many offer cash back on gas purchases, plus it automatically separates your business expenses. 3. Don't forget about smaller deductions that add up: phone bill (business portion), GPS/navigation apps, work uniforms/safety gear, and even things like hand sanitizer or masks if required for medical deliveries. 4. With that income level, you'll definitely want to max out retirement contributions. A SEP-IRA lets you contribute up to 25% of your net self-employment income, which could significantly reduce your tax burden. 5. Keep receipts for EVERYTHING vehicle-related even if you use standard mileage. If your car gets totaled or needs major repairs, you might want to switch methods mid-year. The key is staying organized from the start. It's much harder to reconstruct records later, especially with the IRS scrutinizing high-mileage claims more closely these days.