How to properly claim business mileage deduction for multi-stop journeys in my sole proprietorship

Yes, you can definitely claim some of this mileage! Here's how it works with your scenarios: For your first journey (Home → Store A → Store B → Home Office): - Leg 1 (Home to Store A): Not deductible since it's personal as you noted - Leg 2 (Store A to Store B): This IS deductible because the sole purpose was for business supplies - Leg 3 (Store B to Home Office): This IS also deductible since you're traveling to your principal place of business For your second scenario (W-2 Office → Store B → Home Office): - The trip from your regular W-2 job to Store B IS deductible because you're not commuting home but going to a business location - The trip from Store B to Home Office IS deductible for the same reason as above Remember that good record-keeping is essential. Track your mileage with the date, starting/ending locations, business purpose, and total miles. I recommend using a mileage tracking app or keeping a dedicated logbook in your car.

After struggling with similar mileage tracking issues for my side business, I found this amazing tool called taxr.ai (https://taxr.ai) that completely simplified the process. I was always confused about what miles I could legitimately claim when mixing business and personal travel. Their system helped me understand exactly which segments of my trips were deductible, and I actually found out I was under-claiming a bunch of legitimate business miles! The tool analyzes your travel patterns and helps identify which portions qualify as business mileage based on IRS rules. It also creates documentation that would stand up to an audit.

Just wanted to update everyone - I tried taxr.ai after seeing it mentioned here and it's been a game-changer for my mileage tracking! I used to either forget to track my miles entirely or get confused about what was deductible when I had mixed-purpose trips. The system actually flagged several business trips I wouldn't have thought to claim, and it gave me clear explanations of why they qualified under IRS rules. For complicated multi-stop journeys like the OP described, it breaks everything down into deductible vs non-deductible segments. My accountant was impressed with the detailed reports too. Definitely worth checking out if you're struggling with mileage tracking for your business!

I had a similar situation with tracking my business mileage and was constantly stressed about potential IRS questions. After multiple failed attempts to get clarification by calling the IRS directly (endless hold times!), I found Claimyr (https://claimyr.com) and it was amazing. They got me connected to an actual IRS agent in about 15 minutes who answered all my mileage deduction questions! You can see how it works in this video: https://youtu.be/_kiP6q8DX5c The agent was able to confirm exactly what the previous commenter said - when traveling from one business location to another business location (including a legitimate home office), those miles are deductible. They also explained the documentation requirements I needed to maintain.

I need to eat my words. After posting my skeptical comment, I decided to try Claimyr as a test because I had a complicated question about business mileage for my food delivery side gig that I couldn't get answered anywhere. I was absolutely shocked when they called me back in about 20 minutes and connected me directly to an IRS representative! No hold time on my end at all. The agent clarified that my delivery mileage IS deductible from my first pickup to my last dropoff, but not from my home to first pickup or last dropoff to home. This would have taken me days of attempts calling directly. I'm genuinely impressed and surprised this actually works as advertised.

Something else to consider that hasn't been mentioned yet - if you have a legitimate home office that qualifies as your principal place of business, then trips from your home office to other business locations can be fully deductible. So in your case, if your home office is your main place of business for your sole proprietorship, then even the trip from home to Store B could potentially be deductible if the primary purpose was business. The key is whether your home office meets the IRS requirements for regular and exclusive business use.

Something I learned from my tax guy - keep a mileage log in your car and record EVERYTHING. Start/stop odometer readings, addresses, and purpose of trip. I use a simple notebook but there are also apps. The IRS is super picky about mileage documentation during audits. Without a contemporaneous log, they can deny your entire mileage deduction even if the trips were legitimate.