#julesr - checkout configuration
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Yep, you can combine those together in line_items using mode=subscription:
https://stripe.com/docs/api/checkout/sessions/create?lang=python#create_checkout_session-line_items
For subscription mode, there is a maximum of 20 line items with recurring Prices and 20 line items with one-time Prices. Line items with one-time Prices in will be on the initial invoice only.