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[gusty umbra]

If you want them to have different billing cycles, you would need to create multiple subscriptions.

[white jungle]

Ok, can I charge for two subscriptions at the same time, or do I have to checkout for each individually?

[gusty umbra]

You can charge for both at the same time, you would just need to collect the payment details up front before you create the Subscriptions. This can be done via the Set Up Future Payments workflow: https://stripe.com/docs/payments/save-and-reuse

Once you've collected the payment method details and saved them for future usage, you can use that payment method when creating multiple subscriptions without your customer having to reenter the payment flow