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@Colleen Garrison welcome to the community! i know this doesn't answer your question, but in general i try to stear away from dates with individual checklist items since they're a bit limited (like in things like this). Instead, you can generally do some automation and set up workflows that would create cards for checklist items, and then link them together, and that can be a good way to have the functionality of a "meta card" that has a list of other "subtask" cards with individual tasks, owners and due dates that all relate to a bigger project.