Why wasn't my Smart Calendar Rule triggered?

Smart Calendar Rules will be activated when a reservation is received. Manual blocks won't trigger the rules (the ability to apply a rule to a manual block is currently in Beta).

Also, Smart Calendar Rules can only apply to reservations received after the rules were set, and by default won't affect any existing reservations. For example, if you added a rule that listing A will block listing B, and at the time of the rule's creation there is already a reservation assigned to listing A, listing B won't be blocked.  To avoid this scenario, make sure to mark the "Apply retroactively for existing reservations" checkbox when creating the rule.

The same logic applies when deactivating a Smart Calendar Rule. If a rule is deactivated, listing A won't block listing B, and listing B remains bookable when listing A receives a reservation. Reactivating the rule won't block listing B for the dates of the received reservation, even if the dates of the reservation are futuristic (for example, for 19th-20th March 2090). This is unless you mark the "Apply retroactively for existing reservations" checkbox.

Lastly, there should be a direct rule between the blocking listing to the blocked listing

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