Hi @DM-5249,
However, a transport rule doesn't seem to trigger on emails that were already in quarantine, or I did it wrong. Is this even possible?
I am afraid it's not possible.
Transport rules are applied before emails are put into quarantine (see image below), so per my understanding, it's an expected behavior that the transport rule you created doesn't trigger.
Reference: How EOP works.
As for your idea that adding the "tag" when emails enter the quarantine, it's not feasible either as an email could be quarantined for various reasons.
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