How to Assign Tasks and Send Reminders in Outlook

Open Microsoft Outlook on your computer and toggle off the "New Outlook" switch located in the top right corner.

Once Classic Outlook reloads, click the "Tasks" icon (typically represented by a clipboard) in the bottom-left navigation pane.

Click "New Task" from the ribbon. Enter the task details, click the "Assign Task" button, and enter the staff member's email address.

Check the "Reminder" box, select a specific date and time for the reminder prompt, and click "Send" to dispatch the task to your staff.

Log in to Microsoft 365 on the web, click the App Launcher (waffle icon) in the top left, and select "Planner".

Choose an existing team plan or click "New Plan" to create a dedicated workspace for your staff's tasks.

Click "Add task", type a task name, and set a specific due date. Click "Assign" to select the respective staff member.

Once assigned, Planner automatically handles email notifications and due-date reminders for the assignee, bypassing local Outlook client bugs.

Launch the Microsoft Outlook application on your Mac and click on the "Help" menu in the top Apple menu bar.

Choose "Give Feedback" or "Contact Support" from the dropdown menu.

Explain that due-date reminder emails for To Do tasks are no longer arriving and that the "Remind Me" feature is missing. Submit your report directly to Microsoft.