Hi @Jake Sokol ,
In order to verify your issue, could you please provide some detailed information?
- What MacOS version do you have? Are you currently using an old version of Outlook or a new version of Outlook? For the old version of Outlook, please try to create a new profile and see if the issue continues: Manage profiles or identities in Outlook for Mac For the new version of Outlook, please try to Clear the cache in the new Outlook for Mac
- Have you checked to confirm whether you can set reminders from the Outlook on the Web for the same account? If so, there might be an issue on reminders at the server end.
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