When a Record Matches a Condition automation trigger

Something that keeps tripping me up when writing automations is the behaviour of the "When a Record Matches a Condition" trigger.

This trigger does not always seem to work when I expect it to, i.e. when any part of the record is changed and the record matches the conditions in the trigger, or a record is created and matches the conditions in the trigger.

Does this sound familiar to anyone? Is anyone able to lay out a more precise explanation of how this trigger works?

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