If Stripe is the payment gateway, and the user is not logged in, then checking out a product that creates a recurring order will appear to succeed.
Behind the scenes the initial order goes through fine and a stripe payment is taken, but no customer object is created via Stripe's API. Without a customer object, the payment method cannot be invoked again in the future. (Possibly related but probably not, the Commerce recurring order does not show the anonymous customer's email on it's edit page.)
What's most concerning about this is that it seems to indicate a lack of proper safety checks somewhere down the line.
Closed: cannot reproduce
1.0
Code
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It's likely this issue predates Contrib.social: some issue and comment data are missing.
I'm going to be bold and close this. I am implementing subscriptions with Stripe and anonymous checkout on the Drupal side and out of the box this appears to work. A lot changes in payments in 5+ years. Can re-open if necessary.
Brad are those Stripe native subscriptions, or commerce_recurring subscriptions?