Rethinking Deadline and Late Penalty Policies…Again. Recurring discussions regarding the syllabus pertain to handling excuses, extension requests, and late work, because teachers regularly deal with those issues. Suggested remedies range from giving one-time grace to assuming deception as the norm. If you have been a teacher for any length of time, you already have some sort of policy and have maybe modified it more than once. With this article, I am providing a peek at how and why I morphed from a rigid to a more flexible deadline/late penalty policy and what I observed as a result.