Hi @Brattain, Nathan ,
Welcome to Microsoft Q&A forum and posting your question here.
According to you description, do you mean that you want to disable Calendar reminder automatically dismiss for past events?
In order to verify, what's the version of Outlook you are using?(File > Office Account > About Outlook)
After my search, it is feasible in Outlook365 via File > Options > Advanced > Unchek "Automatically dissmiss reminders for past events".
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