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Can I upgrade / downgrade during a billing period?

Absolutely. We have a 30 day billing period that is in line with your own billing of your Shopify subscription. Shopify has more information on apps prorating, upgrades, and downgrades. They take care of this automatically so you don't get charged twice when changing plans within a billing period: https://help.shopify.com/en/manual/your-account/manage-billing/your-invoice/apps#app-prorating-upgrades-and-downgrades​