I have recently tried to add alumni of the course to this year's addition of the course and in both cases the person never received the email inviting them (back) to the course. All the new people I have added are receiving the email invite just fine. Anyone know what is going on?
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There are a lot of variables in play here (how enrollments are handled at your school/institution, what access options are enabled/disabled, are course shells reused for multiple semesters, etc). It may help if you can tell us what you see on the people page of the course for the person you're trying to add. Does it show the "pending" next to the user's name right now? It could be that they were already part of the course and therefore adding them again really doesn't do anything. Giving us this small bit of info might help us to provide some suggestions or answers for you.