heshamelhattab

[grizzled timber]

Hi 👋 Subscription's billing period changes, and relatedly their recurring payments, are triggered based on the billing_cycle_anchor of the Subscription:
https://stripe.com/docs/api/subscriptions/object#subscription_object-billing_cycle_anchor

It's a bit tedious, but you can update that value for existing Subscriptions. The easier approaches for that are discussed here:
https://stripe.com/docs/billing/subscriptions/billing-cycle#changing
but they're a bit limited.

You can also Subscription Schedules to schedule the billing cycle anchor to be changed in the future, which allows you to avoid using trials
https://stripe.com/docs/billing/subscriptions/subscription-schedules/use-cases#resetting-anchor
Using trials to move the billing cycle anchor is a fine approach, unless you have downstream logic that triggers for trialing Subscriptions, or you use Stripe hosted UIs like the Customer Portal which may look odd if they show a trialing Subscription to a user that doesn't expect to be on a trial.

There isn't a prebuilt feature or setting that allows you to say all Subscription cycle changes should occur at 11:59 PM, you will need to explicitly control that via the billing_cycle_anchor field.