You will be charged when you sign up and then you will be charged every (other) month (depending on the frequency you choose: every 1, 2 or 3 months), on the same day you signed up - i.e.: May 4, June 4, etc. When your wine is billed you will receive an email confirming the charge and then another confirming the shipment. A third email with tracking information will be sent when the wine is on its way to you!