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Have you turn on the escalation log and see if it meets the criteria and also make sure the qualification fields used are not display only fields.
I do run the escalation to cleanup every 15 days and they work fine. I don't have access to system right now to share the qualification.
In the escalation log 'Mailbox ID' LIKE $Mailbox ID$ translate to 'Mailbox ID' LIKE $1$ and escalation works without errors, but a log of a database haven't delete instructions. It seems that the sql statement does not find value for this qualification, although they are exactly there. Why it happens-it's not clear
P.S. My fault - Mailbox ID on AR System Email Messages and Mailbox ID on AR System Email Mailbox Configuration - these are not the same values. Right decision is 'Mailbox ID' = "$Unique Identifier$"
Please check BMC Recommendation for Deleting AR System Email Messages through Escalation