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Trainings cancelled in VSys One versions prior to 2.1 don't generate the "transitions" records needed for this event to work; the training must be cancelled by version 2.1 or later.
If you just make a new training record with a status of Cancelled by volunteer, VSys won't detect that as a "Self-cancelled training". Why? VSys doesn't look at the current status of the training when it's first searching for records to use here, instead it looks for records which once had some status other Cancelled by volunteer but now have one that is Cancelled by volunteer. (That also means that a training whose status was changed by an older version of VSys One won't qualify here, either.)
VSys doesn't know that the volunteer herself did the cancellation, instead it detects that the training's status was changed to Cancelled by volunteer within the Cancelled between window.
One notification is generated for each training record meeting your criteria here, each with the student's name and information about the training.