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You should be able to re-activate it at any time. The permits last for 1 year and this message is just indicating that after that year is up, you will need to re-activate it. As for outages activating via offline, there should be no outage provided the permits are still active.
Here is some more information on the licensing:
Online
https://documentation.red-gate.com/sm12/overview-and-licensing/licensing
Offline:
https://documentation.red-gate.com/sm12/overview-and-licensing/licensing/offline-activation
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"On permit expiry, SQL Monitor needs to be re-activated."
Does this mean that the license cannot be re-activated until it is expired? Can a monitoring outage, however brief, be avoided using offline activation?