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It is safe to reapply the Frontline. Make sure that you get it on skin and keep him from rolling or shaking for at least 5 minutes so he doesn't shake or rub off the liquid before it gets disperses and dry.
We regularly recommend using it every 3 weeks during the worst of the deer tick season because we often start seeing the ticks at just over 3 weeks.
Let me know if you have follow up questions.