If you set billing cycle anchor to subscription over natural cycle of subscription then see below error

Stripe::InvalidRequestError: billing_cycle_anchor cannot be later than next natural billing date (<timestamp>) for plan

Let's use Subscription schedule

billing cycle anchor is not for schedule
Subscription schedule is for schedule Subscription!

For example

you can specify 100 days after as subscription start over subscription cycle.
you can specify only one cycle subscription by "iteration" property. and subscription will be cancel first subscription created.

Code

# Docs

# https://stripe.com/docs/api/subscription_schedules/create
#
# Invoicing workflow | Stripe Billing
# https://stripe.com/docs/billing/invoices/workflow
#
# https://stripe.com/docs/api/invoices/

# Code

require 'stripe'

Stripe::api_key = ENV['STRIPE_SECRET_KEY']

product = Stripe::Product.create(name: "Gold plan #{rand(9999999999)}")
plan = Stripe::Plan.create(interval: 'month', currency: 'jpy', amount: 1000, product: product.id)
tax_rate = Stripe::TaxRate.create(display_name: 'Tax Rate', percentage: 10.0, inclusive: false)
customer = Stripe::Customer.create
payment_method = Stripe::PaymentMethod.create(type: 'card', card: { number: '4242424242424242', exp_year: 2030, exp_month: 01})
customer_payment_method = Stripe::PaymentMethod.attach(payment_method.id, customer: customer.id)

# Subscription create case
# subscription = Stripe::Subscription::create( customer: customer.id, default_payment_method: customer_payment_method.id, items: [{ plan: plan.id }], default_tax_rates: [tax_rate] )

# Set start_date to immediately start schedule
subscription_schedule = Stripe::SubscriptionSchedule.create(
  {
    customer: customer.id,
    # start_date: Time.now.to_i + (24 * 60 * 60 * 100), # e.g specifffy 100 days after
    start_date: Time.now.to_i +  5,
    end_behavior: 'cancel',
    phases: [
      {
        plans:
          [
            {plan: plan.id, quantity: 1},
          ],
          iterations: 1,
          default_payment_method: customer_payment_method.id,
          default_tax_rates: [tax_rate],
      },
    ],
  }
)

puts '-' * 100
puts "Subscription Schedule created"
puts '-' * 100
puts subscription_schedule

puts '-' * 100
puts "Wait until subscription schedule starts"
puts '-' * 100
until subscription_schedule.status == 'active' do
  subscription_schedule = Stripe::SubscriptionSchedule.retrieve(subscription_schedule.id)
  puts subscription_schedule.status
  sleep 2
end

subscription = Stripe::Subscription.retrieve(id: subscription_schedule.subscription, expand: ['schedule', 'latest_invoice'])
puts subscription
puts '-' * 100
puts "Subscription created"
puts '-' * 100

latest_invoice = subscription.latest_invoice
puts latest_invoice
puts '-' * 100
puts "Invoice created"
puts '-' * 100

paid_invoice = Stripe::Invoice.pay(latest_invoice.id)
puts paid_invoice
puts '-' * 100
puts "Invoice payment probably succeeded"
puts '-' * 100
puts 'YAY!'

retrieve_invoice = Stripe::Invoice.retrieve(id: latest_invoice.id, expand: ['subscription','subscription.schedule'])
puts '-' * 100
puts "Retrieve subscription from invoice"
puts '-' * 100
puts retrieve_invoice.subscription
puts '-' * 100
puts "Retrieve subscription schedule from invoice"
puts '-' * 100
puts retrieve_invoice.subscription.schedule

puts '-' * 100
puts "You can See in Dash boards"
puts '-' * 100
puts "https://dashboard.stripe.com/test/subscription_schedules/#{subscription_schedule.id}"
puts "https://dashboard.stripe.com/test/subscriptions/#{subscription.id}"
puts "https://dashboard.stripe.com/test/invoices/#{latest_invoice.id}"

Schedule and pay invoice and cancel subscription case

schedule to future over natural subscription cycle case

Start
2020/04/04
End
2020/05/04

Original by Github issue

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