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WebHook questions - labels

Hi all - I am actively considering implementing EasyShip and part of my evaluation I am thinking of building a webHook service to respond to label creation events and then automatically send the labels to a printer and carry out some other post creation workflows.

A couple of broad WebHook questions here so I can think this through before starting work.

I can test the webhook with the 'Test' functionality which sends a single dummy payload. I am wondering if anyone has experience on what behaviour I would expect when I generate more than on label at once?
Should I expect multiple webhook events - one for each label or
Can I expect to receive one or more webHooks events potentially containing more than one JSON response (perhaps in an array) - one JSON response per label?

Second question: is the label generation process started automatically as soon as I press "Confirm" at the end of the "Create a Shipment" workflow? I am hoping / expecting to start receiving the label creation events in the background as soon as I've hit 'Confirm'

Thanks in advance