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How do free trials behave when cancelled?

We want to give users the option to purchase monthly or annual subscriptions through our Roku channel. In addition, we are thinking about offering free trials on each of those subscriptions. If we give provide a 30 day free trial on both monthly and annual subscriptions, how does that affect subscription canceling?

Say a user purchases an annual subscription that comes with a 30 day free trial. At the end of the 30 days they decide they would like to subscribe to a monthly subscription instead. When is the expiration date for the initial annual subscription? When they subscribe to the monthly subscription do they get a second free trial?
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