Our sweepstakes haven’t started quite yet.
Every day from September 14–20, we’ll give away two $500 gift cards to eligible drivers. For a chance to win in each day’s sweepstakes, please enter daily.
NO PURCHASE NECESSARY, void where prohibited. 18+, U.S. residents with active DOT Number only. Seven daily sweepstakes, starting September 14, 2025, and ending September 20, 2025. Official rules available at https://www.sentry.com/trucking-sweepstakes. Sponsor: Sentry Insurance Company, 1800 North Point Dr., Stevens Point, WI 54481.
No matter what you’re hauling, we understand the risks you face on the road. We have the financial backing and industry experience to help protect and support you.