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Adding a user twice to a schedule

Since the last upgrade, are we no longer able to add a user twice to a schedule? Is there a fix or work around? I tested groups that were created before the update, and I am able to add a user twice to a schedule (first purpose is to include the user in the rotation, the second is for management/escalation purposes that needs to stay in that order.) I also tested groups that were recently created and I am unable to add a user twice to a schedule.

Anyone know the fix?
Thank you.

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