Enter today for your chance to win a $500 gift card!
To show our appreciation for your hard work, dedication, and contribution to keeping our country moving forward, we invite you to enter the 2026 Sentry Insurance Company National Truck Driver Appreciation Week Sweepstakes.
Each day from September 13 through September 19, we’ll select two drivers to win a $500 Visa® gift card. To be eligible to win, please enter daily with a valid DOT Number.
We’ll announce the winners on September 21 and will contact them via email. Each winner will need to respond with their preferred shipping address within 72 hours of receiving the email. If we don’t hear back from a winner in that 72-hour time period, we’ll randomly select another winner in their place.
Thank you again. Good luck in our sweepstakes.
NO PURCHASE NECESSARY, void where prohibited. 18+, U.S. residents with active DOT Number only. Seven daily sweepstakes, starting September 13, 2026, and ending September 19, 2026. See official rules. Sponsor: Sentry Insurance Company, 1800 North Point Dr., Stevens Point, WI 54481.
We help protect truck drivers like you
No matter what or where you’re hauling, we understand the unique risks you face on the road. With financial strength and decades of trucking experience, we're here to help protect you and keep you on schedule.
