We study a signaling game where agents signal their type by choosing when to quit pursuing an uncertain project. High types observe news about project quality and quit when bad news arrives. Low types who do not observe any news may mimic high types by quitting continuously over a phase of time. The reputation dynamics may exhibit nonmonotonicity with respect to quitting time. Our analysis offers a unifying explanation for how and when both early and late quitting can enhance reputation and suggests novel welfare and policy implications.