Merge branch 'stripe_v2/topup' into stripe_v2/credit_sync_job

Gemfile

@@ -159,7 +159,7 @@ gem 'working_hours'
 gem 'pg_search'
 
 # Subscriptions, Billing
-gem 'stripe'
+gem 'stripe', '17.2.0.pre.alpha.2'
 
 ## - helper gems --##
 ## to populate db with sample data

Gemfile.lock

@@ -902,7 +902,7 @@ GEM
     squasher (0.7.2)
     stackprof (0.2.25)
     statsd-ruby (1.5.0)
-    stripe (8.5.0)
+    stripe (17.2.0.pre.alpha.2)
     telephone_number (1.4.20)
     test-prof (1.2.1)
     thor (1.4.0)
@@ -1110,7 +1110,7 @@ DEPENDENCIES
   spring-watcher-listen
   squasher
   stackprof
-  stripe
+  stripe (= 17.2.0.pre.alpha.2)
   telephone_number
   test-prof
   tidewave

app/helpers/billing_helper.rb

@@ -8,7 +8,10 @@ module BillingHelper
     # Return false if not plans are configured, so that no checks are enforced
     return false if default_plan.blank?
 
-    account.custom_attributes['plan_name'].nil? || account.custom_attributes['plan_name'] == default_plan['name']
+    # Handle both string and hash formats for default_plan
+    default_plan_name = default_plan.is_a?(Hash) ? default_plan['name'] : default_plan
+
+    account.custom_attributes['plan_name'].nil? || account.custom_attributes['plan_name'] == default_plan_name
   end
 
   def conversations_this_month(account)

app/policies/account_policy.rb

@@ -30,4 +30,32 @@ class AccountPolicy < ApplicationPolicy
   def toggle_deletion?
     @account_user.administrator?
   end
+
+  def v2_pricing_plans?
+    @account_user.administrator?
+  end
+
+  def v2_topup_options?
+    @account_user.administrator?
+  end
+
+  def v2_topup?
+    @account_user.administrator?
+  end
+
+  def v2_subscribe?
+    @account_user.administrator?
+  end
+
+  def cancel_subscription?
+    @account_user.administrator?
+  end
+
+  def credit_grants?
+    @account_user.administrator?
+  end
+
+  def change_pricing_plan?
+    @account_user.administrator?
+  end
 end

app/views/api/v1/models/_account.json.jbuilder

@@ -6,6 +6,17 @@ if resource.custom_attributes.present?
     json.subscribed_quantity resource.custom_attributes['subscribed_quantity']
     json.subscription_status resource.custom_attributes['subscription_status']
     json.subscription_ends_on resource.custom_attributes['subscription_ends_on']
+    json.stripe_subscription_id resource.custom_attributes['stripe_subscription_id'] if resource.custom_attributes['stripe_subscription_id'].present?
+    json.stripe_billing_version resource.custom_attributes['stripe_billing_version'] if resource.custom_attributes['stripe_billing_version'].present?
+    json.stripe_customer_id resource.custom_attributes['stripe_customer_id'] if resource.custom_attributes['stripe_customer_id'].present?
+    if resource.custom_attributes['pending_stripe_pricing_plan_id'].present?
+      json.pending_stripe_pricing_plan_id resource.custom_attributes['pending_stripe_pricing_plan_id']
+    end
+    if resource.custom_attributes['pending_subscription_quantity'].present?
+      json.pending_subscription_quantity resource.custom_attributes['pending_subscription_quantity']
+    end
+    json.stripe_pricing_plan_id resource.custom_attributes['stripe_pricing_plan_id'] if resource.custom_attributes['stripe_pricing_plan_id'].present?
+    json.next_billing_date resource.custom_attributes['next_billing_date'] if resource.custom_attributes['next_billing_date'].present?
     json.industry resource.custom_attributes['industry'] if resource.custom_attributes['industry'].present?
     json.company_size resource.custom_attributes['company_size'] if resource.custom_attributes['company_size'].present?
     json.timezone resource.custom_attributes['timezone'] if resource.custom_attributes['timezone'].present?

config/locales/en.yml

@@ -119,6 +119,12 @@ en:
       invalid_token: Invalid or expired MFA token
       invalid_credentials: Invalid credentials or verification code
       feature_unavailable: MFA feature is not available. Please configure encryption keys.
+    enterprise:
+      billing:
+        topup_amount_invalid: Topup amount must be greater than 0
+        stripe_customer_required: Customer ID required. Please create a Stripe customer first.
+        lookup_key_not_found: Lookup key not found for pricing plan %{pricing_plan_id}
+        v2_configuration_required: V2 billing configuration is required. Please configure STRIPE_HACKER_PLAN_ID.
   profile:
     mfa:
       enabled: MFA enabled successfully
@@ -435,3 +441,8 @@ en:
       subject: 'Finish setting up %{custom_domain}'
     ssl_status:
       custom_domain_not_configured: 'Custom domain is not configured'
+  enterprise:
+    billing:
+      topup_successful: Topup successful
+      subscription_cancelled: Subscription cancelled
+      pricing_plan_changed: Pricing plan changed

config/routes.rb

@@ -434,6 +434,20 @@ Rails.application.routes.draw do
             end
           end
         end
+
+        namespace :v2 do
+          resources :accounts, only: [] do
+            resource :billing, only: [] do
+              get :credit_grants
+              get :pricing_plans
+              get :topup_options
+              post :topup
+              post :subscribe
+              post :cancel_subscription
+              post :change_pricing_plan
+            end
+          end
+        end
       end
 
       post 'webhooks/stripe', to: 'webhooks/stripe#process_payload'

config/schedule_v2_billing.yml

@@ -0,0 +1,8 @@
+# Stripe V2 Billing Scheduled Jobs
+# Add these to your config/sidekiq_cron.yml or config/schedule.yml
+
+v2_credit_sync:
+  cron: "0 * * * *" # Every hour
+  class: "Enterprise::Billing::CreditSyncJob"
+  queue: low
+  description: "Sync V2 billing credits with Stripe"

enterprise/app/controllers/enterprise/api/v1/accounts_controller.rb

@@ -1,5 +1,6 @@
 class Enterprise::Api::V1::AccountsController < Api::BaseController
   include BillingHelper
+
   before_action :fetch_account
   before_action :check_authorization
   before_action :check_cloud_env, only: [:limits, :toggle_deletion]

enterprise/app/controllers/enterprise/api/v2/billing_controller.rb

@@ -0,0 +1,114 @@
+class Enterprise::Api::V2::BillingController < Api::BaseController
+  before_action :fetch_account
+  before_action :check_authorization
+  before_action :validate_topup_amount, only: [:topup]
+
+  rescue_from StandardError, with: :render_error
+  rescue_from NotImplementedError, with: :render_not_implemented
+
+  def credit_grants
+    service = Enterprise::Billing::V2::CreditManagementService.new(account: @account)
+    grants = service.fetch_credit_grants
+
+    render json: { credit_grants: grants }
+  end
+
+  def pricing_plans
+    plans = Enterprise::Billing::V2::PlanCatalog.plans
+    render json: { pricing_plans: plans }
+  end
+
+  def topup_options
+    options = Enterprise::Billing::V2::TopupCatalog.options
+    render json: { topup_options: options }
+  end
+
+  def topup
+    service = Enterprise::Billing::V2::TopupService.new(account: @account)
+    result = service.create_topup(credits: params[:credits].to_i)
+
+    if result[:success]
+      render json: { success: true, message: result[:message] }
+    else
+      render json: { error: result[:message] }, status: :unprocessable_entity
+    end
+  end
+
+  def subscribe
+    service = Enterprise::Billing::V2::CheckoutSessionService.new(account: @account)
+    redirect_url = service.create_subscription_checkout(
+      pricing_plan_id: params[:pricing_plan_id],
+      quantity: subscription_quantity
+    )
+
+    render json: { redirect_url: redirect_url }
+  end
+
+  def cancel_subscription
+    service = Enterprise::Billing::V2::CancelSubscriptionService.new(account: @account)
+    result = service.cancel_subscription
+
+    if result[:success]
+      # Include account ID and updated attributes for frontend store update
+      @account.reload
+      render json: result.merge(
+        id: @account.id,
+        custom_attributes: @account.custom_attributes
+      )
+    else
+      render json: { error: result[:message] }, status: :unprocessable_entity
+    end
+  end
+
+  def change_pricing_plan
+    service = Enterprise::Billing::V2::ChangePlanService.new(account: @account)
+    result = service.change_plan(
+      new_pricing_plan_id: params[:pricing_plan_id],
+      quantity: params[:quantity]&.to_i
+    )
+
+    if result[:success]
+      # Include account ID and updated attributes for frontend store update
+      @account.reload
+      render json: result.merge(
+        id: @account.id,
+        custom_attributes: @account.custom_attributes
+      )
+    else
+      render json: { error: result[:message] }, status: :unprocessable_entity
+    end
+  end
+
+  private
+
+  def fetch_account
+    @account = current_user.accounts.find(params[:account_id])
+    @current_account_user = @account.account_users.find_by(user_id: current_user.id)
+  end
+
+  def subscription_quantity
+    [params[:quantity].to_i, 1].max
+  end
+
+  def validate_topup_amount
+    return if params[:credits].to_i.positive?
+
+    render json: { error: I18n.t('errors.enterprise.billing.topup_amount_invalid') }, status: :unprocessable_entity
+  end
+
+  def pundit_user
+    {
+      user: current_user,
+      account: @account,
+      account_user: @current_account_user
+    }
+  end
+
+  def render_error(exception)
+    render json: { error: exception.message }, status: :unprocessable_entity
+  end
+
+  def render_not_implemented(exception)
+    render json: { error: exception.message }, status: :not_implemented
+  end
+end

enterprise/app/controllers/enterprise/webhooks/stripe_controller.rb

@@ -6,8 +6,17 @@ class Enterprise::Webhooks::StripeController < ActionController::API
 
     # Attempt to verify the signature. If successful, we'll handle the event
     begin
-      event = Stripe::Webhook.construct_event(payload, sig_header, ENV.fetch('STRIPE_WEBHOOK_SECRET', nil))
+      # Determine which webhook secret to use based on event type
-      ::Enterprise::Billing::HandleStripeEventService.new.perform(event: event)
+      webhook_secret = determine_webhook_secret(payload)
+
+      event = Stripe::Webhook.construct_event(payload, sig_header, webhook_secret)
+
+      # Check if this is a V2 billing event
+      if v2_billing_event?(event.type)
+        ::Enterprise::Billing::V2::WebhookHandlerService.new.perform(event: event)
+      else
+        ::Enterprise::Billing::HandleStripeEventService.new.perform(event: event)
+      end
     # If we fail to verify the signature, then something was wrong with the request
     rescue JSON::ParserError, Stripe::SignatureVerificationError
       # Invalid payload
@@ -18,4 +27,27 @@ class Enterprise::Webhooks::StripeController < ActionController::API
     # We've successfully processed the event without blowing up
     head :ok
   end
+
+  private
+
+  def determine_webhook_secret(payload)
+    # Parse the payload to check event type without full verification
+    parsed_payload = JSON.parse(payload)
+    event_type = parsed_payload['type']
+
+    return ENV.fetch('STRIPE_WEBHOOK_SECRET', nil) if event_type.blank?
+
+    if v2_billing_event?(event_type)
+      ENV.fetch('STRIPE_WEBHOOK_SECRET_V2', nil)
+    else
+      ENV.fetch('STRIPE_WEBHOOK_SECRET', nil)
+    end
+  end
+
+  def v2_billing_event?(event_type)
+    return false if event_type.blank?
+
+    Rails.logger.debug { "V2 billing event: #{event_type}" }
+    event_type.start_with?('v2.')
+  end
 end

enterprise/app/jobs/enterprise/billing/credit_sync_job.rb

@@ -0,0 +1,96 @@
+class Enterprise::Billing::CreditSyncJob < ApplicationJob
+  queue_as :low
+
+  def perform(account = nil)
+    if account
+      sync_single_account(account)
+    else
+      sync_all_accounts
+    end
+  end
+
+  private
+
+  def sync_all_accounts
+    Rails.logger.info '[CreditSyncJob] Starting credit sync for all accounts'
+
+    accounts_with_stripe = Account.where(
+      "custom_attributes->>'stripe_customer_id' IS NOT NULL AND (custom_attributes->>'stripe_billing_version')::integer = 2"
+    )
+    synced_count = 0
+    failed_count = 0
+
+    accounts_with_stripe.find_each do |account|
+      result = sync_account_credits(account)
+      if result[:success]
+        synced_count += 1 if result[:credits_reported].to_i.positive?
+      else
+        failed_count += 1
+        Rails.logger.error "[CreditSyncJob] Failed to sync account #{account.id}: #{result[:message]}"
+      end
+    end
+
+    Rails.logger.info "[CreditSyncJob] Completed. Synced: #{synced_count}, Failed: #{failed_count}"
+    { synced: synced_count, failed: failed_count }
+  end
+
+  def sync_single_account(account)
+    Rails.logger.info "[CreditSyncJob] Syncing credits for account #{account.id}"
+    result = sync_account_credits(account)
+
+    if result[:success]
+      Rails.logger.info "[CreditSyncJob] Successfully synced account #{account.id}"
+    else
+      Rails.logger.error "[CreditSyncJob] Failed to sync account #{account.id}: #{result[:message]}"
+    end
+
+    result
+  end
+
+  def sync_account_credits(account)
+    consumed_credits = account.custom_attributes&.[]('captain_responses_usage').to_i
+    last_synced_credits = account.custom_attributes&.[]('stripe_last_synced_credits').to_i
+    credits_to_report = consumed_credits - last_synced_credits
+
+    if credits_to_report.positive?
+      handle_positive_credits(account, credits_to_report, consumed_credits)
+    elsif credits_to_report.negative?
+      handle_negative_credits(account, credits_to_report, consumed_credits)
+    else
+      { success: true, message: 'Already in sync', credits_reported: 0 }
+    end
+  rescue StandardError => e
+    handle_sync_error(account, e)
+  end
+
+  def handle_positive_credits(account, credits_to_report, consumed_credits)
+    reporter = Enterprise::Billing::V2::UsageReporterService.new(account: account)
+    result = reporter.report(credits_to_report)
+
+    return result unless result[:success]
+
+    update_last_synced_credits(account, consumed_credits)
+    Rails.logger.info "[CreditSyncJob] Account #{account.id}: reported #{credits_to_report} credits (total: #{consumed_credits})"
+    result.merge(credits_reported: credits_to_report)
+  end
+
+  def handle_negative_credits(account, credits_to_report, consumed_credits)
+    Rails.logger.warn "[CreditSyncJob] Account #{account.id} has negative difference: #{credits_to_report}"
+    update_last_synced_credits(account, consumed_credits)
+    { success: true, message: 'Reset sync point due to negative difference', credits_reported: 0 }
+  end
+
+  def handle_sync_error(account, error)
+    Rails.logger.error "[CreditSyncJob] Error syncing account #{account.id}: #{error.message}"
+    Rails.logger.error error.backtrace.join("\n")
+    { success: false, message: error.message }
+  end
+
+  def update_last_synced_credits(account, credits)
+    account.with_lock do
+      current_attributes = account.custom_attributes.present? ? account.custom_attributes.deep_dup : {}
+      current_attributes['stripe_last_synced_credits'] = credits
+      account.update!(custom_attributes: current_attributes)
+    end
+  end
+end

enterprise/app/models/enterprise/account/plan_usage_and_limits.rb

@@ -1,6 +1,13 @@
 module Enterprise::Account::PlanUsageAndLimits
+  # Total credits
   CAPTAIN_RESPONSES = 'captain_responses'.freeze
   CAPTAIN_DOCUMENTS = 'captain_documents'.freeze
+
+  # Response credits breakdown (monthly + topup)
+  CAPTAIN_RESPONSES_MONTHLY = 'captain_responses_monthly'.freeze
+  CAPTAIN_RESPONSES_TOPUP = 'captain_responses_topup'.freeze
+
+  # Usage tracking
   CAPTAIN_RESPONSES_USAGE = 'captain_responses_usage'.freeze
   CAPTAIN_DOCUMENTS_USAGE = 'captain_documents_usage'.freeze
 
@@ -16,8 +23,7 @@ module Enterprise::Account::PlanUsageAndLimits
   end
 
   def increment_response_usage
-    current_usage = custom_attributes[CAPTAIN_RESPONSES_USAGE].to_i || 0
+    custom_attributes[CAPTAIN_RESPONSES_USAGE] = (custom_attributes[CAPTAIN_RESPONSES_USAGE].to_i || 0) + 1
-    custom_attributes[CAPTAIN_RESPONSES_USAGE] = current_usage + 1
     save
   end
 
@@ -58,11 +64,12 @@ module Enterprise::Account::PlanUsageAndLimits
                else
                  custom_attributes[CAPTAIN_RESPONSES_USAGE].to_i || 0
                end
-
     consumed = 0 if consumed.negative?
 
     {
       total_count: total_count,
+      monthly: (self[:limits][CAPTAIN_RESPONSES_MONTHLY].to_i if type == :responses),
+      topup: (self[:limits][CAPTAIN_RESPONSES_TOPUP].to_i if type == :responses),
       current_available: (total_count - consumed).clamp(0, total_count),
       consumed: consumed
     }
@@ -96,17 +103,12 @@ module Enterprise::Account::PlanUsageAndLimits
   end
 
   def agent_limits
-    subscribed_quantity = custom_attributes['subscribed_quantity']
+    custom_attributes['subscribed_quantity'] || get_limits(:agents)
-    subscribed_quantity || get_limits(:agents)
   end
 
   def get_limits(limit_name)
     config_name = "ACCOUNT_#{limit_name.to_s.upcase}_LIMIT"
-    return self[:limits][limit_name.to_s] if self[:limits][limit_name.to_s].present?
+    self[:limits][limit_name.to_s].presence || GlobalConfig.get(config_name)[config_name].presence || ChatwootApp.max_limit
-
-    return GlobalConfig.get(config_name)[config_name] if GlobalConfig.get(config_name)[config_name].present?
-
-    ChatwootApp.max_limit
   end
 
   def validate_limit_keys
@@ -119,7 +121,9 @@ module Enterprise::Account::PlanUsageAndLimits
         'inboxes' => { 'type': 'number' },
         'agents' => { 'type': 'number' },
         'captain_responses' => { 'type': 'number' },
-        'captain_documents' => { 'type': 'number' }
+        'captain_documents' => { 'type': 'number' },
+        'captain_responses_monthly' => { 'type': 'number' },
+        'captain_responses_topup' => { 'type': 'number' }
       },
       'required' => [],
       'additionalProperties' => false

enterprise/app/services/enterprise/billing/concerns/billing_intent_workflow.rb

@@ -0,0 +1,14 @@
+module Enterprise::Billing::Concerns::BillingIntentWorkflow
+  extend ActiveSupport::Concern
+
+  private
+
+  # Execute a billing intent with automatic reserve and commit
+  def execute_billing_intent(intent_params)
+    intent = create_billing_intent(intent_params)
+    reserve_billing_intent(intent['id'])
+    yield(intent) if block_given?
+    commit_billing_intent(intent['id'])
+    intent
+  end
+end

enterprise/app/services/enterprise/billing/concerns/plan_data_helper.rb

@@ -0,0 +1,24 @@
+module Enterprise::Billing::Concerns::PlanDataHelper
+  extend ActiveSupport::Concern
+
+  private
+
+  def fetch_plan_version(plan_id)
+    plan = retrieve_pricing_plan(plan_id)
+    version = extract_attribute(plan, :latest_version)
+    raise StandardError, "No version found for pricing plan #{plan_id}" if version.blank?
+
+    version
+  end
+
+  def fetch_plan_lookup_key(plan_id)
+    lookup_key = Enterprise::Billing::V2::PlanCatalog.lookup_key_for_plan(plan_id)
+    raise StandardError, "Lookup key not found for pricing plan #{plan_id}" unless lookup_key
+
+    lookup_key
+  end
+
+  def plan_display_name(plan_id)
+    Enterprise::Billing::V2::PlanCatalog.definition_for(plan_id)&.dig(:display_name) || 'Unknown Plan'
+  end
+end

enterprise/app/services/enterprise/billing/concerns/plan_feature_manager.rb

@@ -0,0 +1,87 @@
+module Enterprise::Billing::Concerns::PlanFeatureManager
+  extend ActiveSupport::Concern
+
+  # Plan hierarchy: Hacker (default) -> Startup -> Business -> Enterprise
+  # Each higher tier includes all features from the lower tiers
+
+  # Basic features available starting with the Startup plan
+  STARTUP_PLAN_FEATURES = %w[
+    inbound_emails
+    help_center
+    campaigns
+    team_management
+    channel_twitter
+    channel_facebook
+    channel_email
+    channel_instagram
+    captain_integration
+    advanced_search_indexing
+    advanced_search
+  ].freeze
+
+  # Additional features available starting with the Business plan
+  BUSINESS_PLAN_FEATURES = %w[sla custom_roles].freeze
+
+  # Additional features available only in the Enterprise plan
+  ENTERPRISE_PLAN_FEATURES = %w[audit_logs disable_branding saml].freeze
+
+  def update_plan_features(plan_name)
+    if plan_name.blank? || plan_name == 'Hacker'
+      disable_all_premium_features
+    else
+      enable_features_for_current_plan(plan_name)
+    end
+
+    # Enable any manually managed features configured in internal_attributes
+    enable_account_manually_managed_features
+
+    account.save!
+  end
+
+  def disable_all_premium_features
+    # Disable all features (for default Hacker plan or during plan changes)
+    account.disable_features(*STARTUP_PLAN_FEATURES)
+    account.disable_features(*BUSINESS_PLAN_FEATURES)
+    account.disable_features(*ENTERPRISE_PLAN_FEATURES)
+  end
+
+  def enable_features_for_current_plan(plan_name)
+    disable_all_premium_features
+    enable_plan_specific_features(plan_name)
+  end
+
+  def enable_plan_specific_features(plan_name)
+    return if plan_name.blank?
+
+    # Enable features based on plan hierarchy
+    case plan_name
+    when 'Startups'
+      # Startup plan gets the basic features
+      account.enable_features(*STARTUP_PLAN_FEATURES)
+    when 'Business'
+      # Business plan gets Startup features + Business features
+      account.enable_features(*STARTUP_PLAN_FEATURES)
+      account.enable_features(*BUSINESS_PLAN_FEATURES)
+    when 'Enterprise'
+      # Enterprise plan gets all features
+      account.enable_features(*STARTUP_PLAN_FEATURES)
+      account.enable_features(*BUSINESS_PLAN_FEATURES)
+      account.enable_features(*ENTERPRISE_PLAN_FEATURES)
+    end
+  end
+
+  def reset_captain_usage
+    account.reset_response_usage if account.respond_to?(:reset_response_usage)
+  end
+
+  private
+
+  def enable_account_manually_managed_features
+    # Get manually managed features from internal attributes using the service
+    service = Internal::Accounts::InternalAttributesService.new(account)
+    features = service.manually_managed_features
+
+    # Enable each feature
+    account.enable_features(*features) if features.present?
+  end
+end

enterprise/app/services/enterprise/billing/concerns/plan_provisioning_helper.rb

@@ -0,0 +1,13 @@
+module Enterprise::Billing::Concerns::PlanProvisioningHelper
+  extend ActiveSupport::Concern
+
+  private
+
+  def provision_new_plan(new_pricing_plan_id)
+    plan_definition = Enterprise::Billing::V2::PlanCatalog.definition_for(new_pricing_plan_id)
+    return unless plan_definition
+
+    plan_name = plan_definition[:display_name]
+    enable_plan_specific_features(plan_name) if plan_name.present?
+  end
+end

enterprise/app/services/enterprise/billing/concerns/proration_line_item_builder.rb

@@ -0,0 +1,92 @@
+module Enterprise::Billing::Concerns::ProrationLineItemBuilder
+  extend ActiveSupport::Concern
+  include Enterprise::Billing::Concerns::PlanDataHelper
+
+  private
+
+  def build_proration_line_items(context, proration_data)
+    return build_seat_change_line_items(context, proration_data) if seat_only_change?(context)
+
+    build_plan_change_line_items(context, proration_data)
+  end
+
+  def seat_only_change?(context)
+    !context[:plan_changed] && context[:seats_changed]
+  end
+
+  def build_seat_change_line_items(context, proration_data)
+    [{
+      amount: (proration_data[:net_amount] * 100).to_i,
+      description: build_seat_change_description(context),
+      metadata: build_seat_change_metadata(context, proration_data)
+    }]
+  end
+
+  def build_plan_change_line_items(context, proration_data)
+    line_items = []
+    old_plan_name = plan_display_name(context[:old_plan_id])
+    new_plan_name = plan_display_name(context[:target_plan_id])
+
+    line_items << build_credit_line_item(context, proration_data, old_plan_name) if proration_data[:credit_amount].positive?
+    line_items << build_charge_line_item(context, proration_data, new_plan_name) if proration_data[:charge_amount].positive?
+
+    line_items
+  end
+
+  def build_credit_line_item(context, proration_data, old_plan_name)
+    {
+      amount: -(proration_data[:credit_amount] * 100).to_i,
+      description: credit_description(old_plan_name, context[:old_quantity]),
+      metadata: credit_metadata(old_plan_name, context[:old_quantity], proration_data[:days_remaining])
+    }
+  end
+
+  def build_charge_line_item(context, proration_data, new_plan_name)
+    {
+      amount: (proration_data[:charge_amount] * 100).to_i,
+      description: charge_description(new_plan_name, context[:target_quantity]),
+      metadata: charge_metadata(new_plan_name, context[:target_quantity], proration_data[:days_remaining])
+    }
+  end
+
+  def credit_description(plan_name, quantity)
+    "Credit for unused time on #{plan_name} (#{quantity} seat#{quantity > 1 ? 's' : ''})"
+  end
+
+  def charge_description(plan_name, quantity)
+    "Prorated charge for #{plan_name} (#{quantity} seat#{quantity > 1 ? 's' : ''})"
+  end
+
+  def build_seat_change_description(context)
+    plan_name = plan_display_name(context[:target_plan_id])
+    change_type = context[:target_quantity] > context[:old_quantity] ? 'increase' : 'decrease'
+    quantity_diff = (context[:target_quantity] - context[:old_quantity]).abs
+
+    "Seat #{change_type} for #{plan_name}: #{context[:old_quantity]} → #{context[:target_quantity]} " \
+      "seats (#{quantity_diff} seat#{quantity_diff > 1 ? 's' : ''})"
+  end
+
+  def base_metadata(type, days_remaining, **additional_fields)
+    {
+      type: type,
+      days_remaining: days_remaining,
+      billing_version: 'v2'
+    }.merge(additional_fields)
+  end
+
+  def credit_metadata(plan_name, quantity, days_remaining)
+    base_metadata('proration_credit', days_remaining, old_plan: plan_name, old_quantity: quantity)
+  end
+
+  def charge_metadata(plan_name, quantity, days_remaining)
+    base_metadata('proration_charge', days_remaining, new_plan: plan_name, new_quantity: quantity)
+  end
+
+  def build_seat_change_metadata(context, proration_data)
+    base_metadata('seat_change', proration_data[:days_remaining],
+                  plan_name: plan_display_name(context[:target_plan_id]),
+                  old_quantity: context[:old_quantity],
+                  new_quantity: context[:target_quantity],
+                  quantity_change: context[:target_quantity] - context[:old_quantity])
+  end
+end

enterprise/app/services/enterprise/billing/concerns/stripe_v2_client_helper.rb

@@ -0,0 +1,67 @@
+module Enterprise::Billing::Concerns::StripeV2ClientHelper
+  extend ActiveSupport::Concern
+
+  private
+
+  # Stripe client instance with API key
+  def stripe_client
+    @stripe_client ||= Stripe::StripeClient.new(ENV.fetch('STRIPE_SECRET_KEY', nil))
+  end
+
+  # Pricing Plan Subscriptions
+  def retrieve_pricing_plan_subscription(subscription_id)
+    stripe_client.v2.billing.pricing_plan_subscriptions.retrieve(subscription_id)
+  end
+
+  # Pricing Plans
+  def retrieve_pricing_plan(pricing_plan_id)
+    stripe_client.v2.billing.pricing_plans.retrieve(pricing_plan_id)
+  end
+
+  def retrieve_billing_cadence(cadence_id)
+    stripe_client.v2.billing.cadences.retrieve(cadence_id)
+  end
+
+  def create_billing_intent(params)
+    response = Faraday.post('https://api.stripe.com/v2/billing/intents') do |req|
+      req.headers['Authorization'] = "Bearer #{ENV.fetch('STRIPE_SECRET_KEY', nil)}"
+      req.headers['Stripe-Version'] = default_stripe_version
+      req.headers['Content-Type'] = 'application/json'
+      req.body = params.to_json
+    end
+
+    JSON.parse(response.body)
+  end
+
+  def reserve_billing_intent(billing_intent_id)
+    stripe_client.v2.billing.intents.reserve(billing_intent_id)
+  end
+
+  def commit_billing_intent(billing_intent_id)
+    stripe_client.v2.billing.intents.commit(billing_intent_id)
+  end
+
+  # Checkout Sessions (V1 API but used with V2 plans)
+  def create_checkout_session(params)
+    Stripe::Checkout::Session.create(params, { stripe_version: checkout_stripe_version })
+  end
+
+  # Credit Grants (V1 API but used with V2)
+  def retrieve_credit_grant(grant_id)
+    Stripe::Billing::CreditGrant.retrieve(grant_id)
+  end
+
+  def default_stripe_version
+    '2025-10-29.preview'
+  end
+
+  def checkout_stripe_version
+    '2025-10-29.preview;checkout_product_catalog_preview=v1'
+  end
+
+  def extract_attribute(object, key)
+    return object.public_send(key) if object.respond_to?(key)
+
+    object[key.to_s]
+  end
+end

enterprise/app/services/enterprise/billing/concerns/subscription_data_manager.rb

@@ -0,0 +1,41 @@
+module Enterprise::Billing::Concerns::SubscriptionDataManager
+  extend ActiveSupport::Concern
+
+  private
+
+  def fetch_subscription_metadata
+    subscription_id = fetch_subscription_id
+    subscription = retrieve_pricing_plan_subscription(subscription_id)
+    cadence_id = extract_cadence_id(subscription)
+    cadence = retrieve_billing_cadence(cadence_id)
+    next_billing_date = extract_attribute(cadence, :next_billing_date)
+
+    store_next_billing_date(next_billing_date)
+
+    {
+      subscription_id: subscription_id,
+      subscription: subscription,
+      cadence_id: cadence_id,
+      cadence: cadence,
+      next_billing_date: next_billing_date
+    }
+  end
+
+  def fetch_subscription_id
+    subscription_id = custom_attribute('stripe_subscription_id')
+    raise StandardError, 'No pricing plan subscription ID found' if subscription_id.blank?
+
+    subscription_id
+  end
+
+  def extract_cadence_id(subscription)
+    cadence_id = extract_attribute(subscription, :billing_cadence)
+    raise StandardError, 'No billing cadence found in subscription' if cadence_id.blank?
+
+    cadence_id
+  end
+
+  def store_next_billing_date(next_billing_date)
+    update_custom_attributes({ 'next_billing_date' => next_billing_date })
+  end
+end

enterprise/app/services/enterprise/billing/create_stripe_customer_service.rb

@@ -1,4 +1,6 @@
 class Enterprise::Billing::CreateStripeCustomerService
+  include Enterprise::Billing::Concerns::PlanFeatureManager
+
   pattr_initialize [:account!]
 
   DEFAULT_QUANTITY = 2
@@ -6,22 +8,11 @@ class Enterprise::Billing::CreateStripeCustomerService
   def perform
     return if existing_subscription?
 
+    raise_config_error unless v2_configs_present?
+
     customer_id = prepare_customer_id
-    subscription = Stripe::Subscription.create(
+    update_account_for_v2_billing(customer_id)
-      {
+    enable_plan_specific_features('Hacker')
-        customer: customer_id,
-        items: [{ price: price_id, quantity: default_quantity }]
-      }
-    )
-    account.update!(
-      custom_attributes: {
-        stripe_customer_id: customer_id,
-        stripe_price_id: subscription['plan']['id'],
-        stripe_product_id: subscription['plan']['product'],
-        plan_name: default_plan['name'],
-        subscribed_quantity: subscription['quantity']
-      }
-    )
   end
 
   private
@@ -35,22 +26,16 @@ class Enterprise::Billing::CreateStripeCustomerService
     customer_id
   end
 
-  def default_quantity
-    default_plan['default_quantity'] || DEFAULT_QUANTITY
-  end
-
   def billing_email
     account.administrators.first.email
   end
 
-  def default_plan
+  def v2_configs_present?
-    installation_config = InstallationConfig.find_by(name: 'CHATWOOT_CLOUD_PLANS')
+    InstallationConfig.find_by(name: 'STRIPE_HACKER_PLAN_ID').present?
-    @default_plan ||= installation_config.value.first
   end
 
-  def price_id
+  def raise_config_error
-    price_ids = default_plan['price_ids']
+    raise StandardError, I18n.t('errors.enterprise.billing.v2_configuration_required')
-    price_ids.first
   end
 
   def existing_subscription?
@@ -66,4 +51,23 @@ class Enterprise::Billing::CreateStripeCustomerService
     )
     subscriptions.data.present?
   end
+
+  def update_account_for_v2_billing(customer_id)
+    hacker_plan_config = InstallationConfig.find_by(name: 'STRIPE_HACKER_PLAN_ID')
+
+    attributes = {
+      stripe_customer_id: customer_id,
+      stripe_billing_version: 2
+    }
+
+    if hacker_plan_config&.value.present?
+      attributes.merge!(
+        stripe_pricing_plan_id: hacker_plan_config.value,
+        plan_name: 'Hacker',
+        subscribed_quantity: DEFAULT_QUANTITY
+      )
+    end
+
+    account.update!(custom_attributes: attributes)
+  end
 end

enterprise/app/services/enterprise/billing/handle_stripe_event_service.rb

@@ -1,30 +1,9 @@
 class Enterprise::Billing::HandleStripeEventService
+  include Enterprise::Billing::Concerns::PlanFeatureManager
+  include Enterprise::Billing::Concerns::StripeV2ClientHelper
+
   CLOUD_PLANS_CONFIG = 'CHATWOOT_CLOUD_PLANS'.freeze
 
-  # Plan hierarchy: Hacker (default) -> Startups -> Business -> Enterprise
-  # Each higher tier includes all features from the lower tiers
-
-  # Basic features available starting with the Startups plan
-  STARTUP_PLAN_FEATURES = %w[
-    inbound_emails
-    help_center
-    campaigns
-    team_management
-    channel_twitter
-    channel_facebook
-    channel_email
-    channel_instagram
-    captain_integration
-    advanced_search_indexing
-    advanced_search
-  ].freeze
-
-  # Additional features available starting with the Business plan
-  BUSINESS_PLAN_FEATURES = %w[sla custom_roles].freeze
-
-  # Additional features available only in the Enterprise plan
-  ENTERPRISE_PLAN_FEATURES = %w[audit_logs disable_branding saml].freeze
-
   def perform(event:)
     @event = event
 
@@ -33,6 +12,8 @@ class Enterprise::Billing::HandleStripeEventService
       process_subscription_updated
     when 'customer.subscription.deleted'
       process_subscription_deleted
+    when 'billing.credit_grant.created'
+      process_credit_grant_created
     else
       Rails.logger.debug { "Unhandled event type: #{event.type}" }
     end
@@ -47,7 +28,8 @@ class Enterprise::Billing::HandleStripeEventService
     return if plan.blank? || account.blank?
 
     update_account_attributes(subscription, plan)
-    update_plan_features
+    plan_name = account.custom_attributes['plan_name']
+    update_plan_features(plan_name)
     reset_captain_usage
   end
 
@@ -73,65 +55,22 @@ class Enterprise::Billing::HandleStripeEventService
     Enterprise::Billing::CreateStripeCustomerService.new(account: account).perform
   end
 
-  def update_plan_features
-    if default_plan?
-      disable_all_premium_features
-    else
-      enable_features_for_current_plan
-    end
-
-    # Enable any manually managed features configured in internal_attributes
-    enable_account_manually_managed_features
-
-    account.save!
-  end
-
-  def disable_all_premium_features
-    # Disable all features (for default Hacker plan)
-    account.disable_features(*STARTUP_PLAN_FEATURES)
-    account.disable_features(*BUSINESS_PLAN_FEATURES)
-    account.disable_features(*ENTERPRISE_PLAN_FEATURES)
-  end
-
-  def enable_features_for_current_plan
-    # First disable all premium features to handle downgrades
-    disable_all_premium_features
-
-    # Then enable features based on the current plan
-    enable_plan_specific_features
-  end
-
-  def reset_captain_usage
-    account.reset_response_usage
-  end
-
-  def enable_plan_specific_features
-    plan_name = account.custom_attributes['plan_name']
-    return if plan_name.blank?
-
-    # Enable features based on plan hierarchy
-    case plan_name
-    when 'Startups'
-      # Startups plan gets the basic features
-      account.enable_features(*STARTUP_PLAN_FEATURES)
-    when 'Business'
-      # Business plan gets Startups features + Business features
-      account.enable_features(*STARTUP_PLAN_FEATURES)
-      account.enable_features(*BUSINESS_PLAN_FEATURES)
-    when 'Enterprise'
-      # Enterprise plan gets all features
-      account.enable_features(*STARTUP_PLAN_FEATURES)
-      account.enable_features(*BUSINESS_PLAN_FEATURES)
-      account.enable_features(*ENTERPRISE_PLAN_FEATURES)
-    end
-  end
-
   def subscription
     @subscription ||= @event.data.object
   end
 
   def account
-    @account ||= Account.where("custom_attributes->>'stripe_customer_id' = ?", subscription.customer).first
+    @account ||= begin
+      customer_id = if @event.type.start_with?('billing.credit_grant')
+                      # Credit grant events have customer directly on the object
+                      @event.data.object.respond_to?(:customer) ? @event.data.object.customer : @event.data.object['customer']
+                    else
+                      # Subscription events have customer on subscription
+                      subscription.customer
+                    end
+
+      Account.where("custom_attributes->>'stripe_customer_id' = ?", customer_id).first
+    end
   end
 
   def find_plan(plan_id)
@@ -139,18 +78,60 @@ class Enterprise::Billing::HandleStripeEventService
     cloud_plans.find { |config| config['product_id'].include?(plan_id) }
   end
 
-  def default_plan?
+  def process_credit_grant_created
-    cloud_plans = InstallationConfig.find_by(name: CLOUD_PLANS_CONFIG)&.value || []
+    grant_id = extract_credit_grant_id(@event.data.object)
-    default_plan = cloud_plans.first || {}
+    return if grant_id.blank?
-    account.custom_attributes['plan_name'] == default_plan['name']
+
+    # Retrieve the full credit grant object from Stripe API
+    grant = retrieve_credit_grant(grant_id)
+    return if grant.blank?
+
+    amount = extract_credit_amount(grant)
+    return if amount.zero?
+
+    grant_type = extract_grant_type(grant)
+    service = Enterprise::Billing::V2::CreditManagementService.new(account: account)
+    if grant_type == 'monetary'
+      service.add_response_topup_credits(amount)
+    else
+      service.sync_monthly_response_credits(amount)
+    end
   end
 
-  def enable_account_manually_managed_features
+  def extract_credit_grant_id(grant_object)
-    # Get manually managed features from internal attributes using the service
+    grant_object.respond_to?(:id) ? grant_object.id : grant_object['id']
-    service = Internal::Accounts::InternalAttributesService.new(account)
+  end
-    features = service.manually_managed_features
 
-    # Enable each feature
+  def extract_grant_type(grant)
-    account.enable_features(*features) if features.present?
+    amount_object = extract_attribute(grant, :amount)
+    return 'monetary' if amount_object.blank?
+
+    type = extract_attribute(amount_object, :type)
+    return 'monetary' if type.blank?
+
+    type
+  end
+
+  def extract_credit_amount(grant)
+    # First, try to get credits from metadata
+    metadata = extract_attribute(grant, :metadata)
+    if metadata
+      credits = extract_attribute(metadata, :credits)
+      return credits.to_i if credits.present? && credits.to_i.positive?
+    end
+    amount = extract_attribute(grant, :amount)
+    return 0 if amount.blank?
+
+    custom_pricing_unit = extract_attribute(amount, :custom_pricing_unit)
+    return 0 if custom_pricing_unit.blank?
+
+    value = extract_attribute(custom_pricing_unit, :value)
+    return 0 if value.blank?
+
+    value.to_i
+  end
+
+  def extract_attribute(object, attribute)
+    object.respond_to?(attribute) ? object.public_send(attribute) : object[attribute.to_s]
   end
 end

enterprise/app/services/enterprise/billing/v2/base_service.rb

@@ -0,0 +1,80 @@
+class Enterprise::Billing::V2::BaseService
+  attr_reader :account
+
+  def initialize(account:)
+    @account = account
+  end
+
+  private
+
+  def stripe_client
+    @stripe_client ||= Stripe::StripeClient.new(
+      api_key: ENV.fetch('STRIPE_SECRET_KEY', nil)
+    )
+  end
+
+  def response_monthly_credits
+    account.limits&.[]('captain_responses_monthly').to_i
+  end
+
+  def response_topup_credits
+    account.limits&.[]('captain_responses_topup').to_i
+  end
+
+  def response_usage
+    account.custom_attributes&.[]('captain_responses_usage').to_i
+  end
+
+  # Update response credits (monthly/topup with auto-calculation of total)
+  def update_response_credits(monthly: nil, topup: nil)
+    # Calculate and update total in limits hash ONLY
+    return if monthly.nil? && topup.nil?
+
+    new_monthly = monthly || response_monthly_credits
+    new_topup = topup || response_topup_credits
+    total_credits = new_monthly + new_topup
+    limits = {
+      'captain_responses_monthly' => new_monthly,
+      'captain_responses_topup' => new_topup,
+      'captain_responses' => total_credits
+    }
+    update_limits(limits)
+  end
+
+  def update_limits(updates)
+    return if updates.blank?
+
+    account.update!(limits: (account.limits || {}).merge(updates.transform_keys(&:to_s)))
+  end
+
+  def update_custom_attributes(updates)
+    return if updates.blank?
+
+    account.update!(custom_attributes: (account.custom_attributes || {}).merge(updates.transform_keys(&:to_s)))
+  end
+
+  def custom_attribute(key)
+    account.custom_attributes&.[](key.to_s)
+  end
+
+  def with_locked_account(&)
+    account.with_lock(&)
+  end
+
+  # Convenient accessors for common attributes
+  def stripe_customer_id
+    custom_attribute('stripe_customer_id')
+  end
+
+  def stripe_subscription_id
+    custom_attribute('stripe_subscription_id')
+  end
+
+  def pricing_plan_id
+    custom_attribute('stripe_pricing_plan_id')
+  end
+
+  def subscribed_quantity
+    custom_attribute('subscribed_quantity').to_i
+  end
+end

enterprise/app/services/enterprise/billing/v2/cancel_subscription_service.rb

@@ -0,0 +1,60 @@
+class Enterprise::Billing::V2::CancelSubscriptionService < Enterprise::Billing::V2::BaseService
+  include Enterprise::Billing::Concerns::PlanFeatureManager
+  include Enterprise::Billing::Concerns::StripeV2ClientHelper
+  include Enterprise::Billing::Concerns::BillingIntentWorkflow
+  include Enterprise::Billing::Concerns::SubscriptionDataManager
+
+  # Cancel subscription using Stripe's V2 Billing Intent API
+  # Creates a deactivate billing intent for the pricing plan subscription
+  # Subscription remains active until the end of the current billing period
+  #
+  # @return [Hash] { success:, cancel_at_period_end:, period_end:, message: }
+  #
+  def cancel_subscription
+    with_locked_account do
+      metadata = fetch_subscription_metadata
+      intent_params = build_deactivate_params(metadata[:subscription_id], metadata[:cadence_id])
+      execute_billing_intent(intent_params)
+      update_account_status(metadata[:next_billing_date])
+      build_success_response
+    end
+  rescue Stripe::StripeError => e
+    { success: false, message: "Stripe error: #{e.message}" }
+  rescue StandardError => e
+    { success: false, message: "Cancellation error: #{e.message}" }
+  end
+
+  private
+
+  def build_deactivate_params(subscription_id, cadence_id)
+    {
+      cadence: cadence_id,
+      currency: 'usd',
+      actions: [{
+        type: 'deactivate',
+        deactivate: {
+          type: 'pricing_plan_subscription_details',
+          pricing_plan_subscription_details: { pricing_plan_subscription: subscription_id }
+        }
+      }]
+    }
+  end
+
+  def update_account_status(next_billing_date)
+    # Mark subscription as cancelling (will be cancelled at period end)
+    # Store next_billing_date so the UI can show when the subscription ends
+    update_custom_attributes({
+                               'subscription_status' => 'cancel_at_period_end',
+                               'subscription_cancelled_at' => Time.current.iso8601,
+                               'subscription_ends_at' => next_billing_date
+                             })
+  end
+
+  def build_success_response
+    {
+      success: true,
+      cancel_at_period_end: true,
+      message: 'Subscription cancellation initiated. It will be deactivated at the end of the current billing period.'
+    }
+  end
+end

enterprise/app/services/enterprise/billing/v2/change_plan_service.rb

@@ -0,0 +1,154 @@
+class Enterprise::Billing::V2::ChangePlanService < Enterprise::Billing::V2::BaseService
+  include Enterprise::Billing::Concerns::PlanFeatureManager
+  include Enterprise::Billing::Concerns::ProrationLineItemBuilder
+  include Enterprise::Billing::Concerns::StripeV2ClientHelper
+  include Enterprise::Billing::Concerns::PlanProvisioningHelper
+  include Enterprise::Billing::Concerns::BillingIntentWorkflow
+  include Enterprise::Billing::Concerns::SubscriptionDataManager
+  include Enterprise::Billing::Concerns::PlanDataHelper
+
+  def change_plan(new_pricing_plan_id: nil, quantity: nil)
+    validation_error = validate_parameters(new_pricing_plan_id, quantity)
+    return validation_error if validation_error
+
+    with_locked_account do
+      perform_subscription_change(new_pricing_plan_id, quantity)
+    end
+  end
+
+  private
+
+  def validate_parameters(new_pricing_plan_id, quantity)
+    return { success: false, message: 'Must specify either new_pricing_plan_id or quantity' } if new_pricing_plan_id.nil? && quantity.nil?
+    return { success: false, message: 'Invalid quantity' } if !quantity.nil? && !quantity.positive?
+
+    # Validate customer has a default payment method using common service
+    payment_service = Enterprise::Billing::V2::InvoicePaymentService.new(account: account)
+    payment_method_validation = payment_service.validate_payment_method
+    return payment_method_validation unless payment_method_validation.nil?
+
+    nil
+  end
+
+  def perform_subscription_change(new_pricing_plan_id, quantity)
+    change_context = build_change_context(new_pricing_plan_id, quantity)
+    return no_change_response(change_context) unless change_required?(change_context)
+
+    execute_change(change_context)
+  end
+
+  def build_change_context(new_pricing_plan_id, quantity)
+    old_plan_id = pricing_plan_id
+    old_quantity = subscribed_quantity
+    target_plan_id = new_pricing_plan_id || old_plan_id
+    target_quantity = quantity || old_quantity
+
+    {
+      old_plan_id: old_plan_id,
+      old_quantity: old_quantity,
+      target_plan_id: target_plan_id,
+      target_quantity: target_quantity,
+      plan_changed: old_plan_id != target_plan_id,
+      seats_changed: old_quantity != target_quantity
+    }
+  end
+
+  def change_required?(context)
+    context[:plan_changed] || context[:seats_changed]
+  end
+
+  def no_change_response(context)
+    plan_name = plan_display_name(context[:target_plan_id])
+    { success: false, message: "Subscription already has plan #{plan_name} with #{context[:target_quantity]} seat(s)" }
+  end
+
+  def execute_change(context)
+    # Create and execute billing intent to update the Stripe subscription
+    intent_params = build_change_plan_params(context[:target_plan_id], context[:target_quantity])
+    execute_billing_intent(intent_params)
+
+    next_billing_date = custom_attribute('next_billing_date')
+    proration_data = calculate_proration(
+      old_plan_id: context[:old_plan_id],
+      new_plan_id: context[:target_plan_id],
+      old_quantity: context[:old_quantity],
+      new_quantity: context[:target_quantity],
+      next_billing_date: next_billing_date
+    )
+    line_items = build_proration_line_items(context, proration_data)
+    create_and_charge_invoice(line_items)
+
+    update_account_plan(context[:target_plan_id], context[:target_quantity], next_billing_date)
+    provision_new_plan(context[:target_plan_id]) if context[:plan_changed]
+
+    { success: true, message: 'Plan change successful' }
+  end
+
+  def build_change_plan_params(new_pricing_plan_id, quantity)
+    metadata = fetch_subscription_metadata
+    plan_version = fetch_plan_version(new_pricing_plan_id)
+    lookup_key = fetch_plan_lookup_key(new_pricing_plan_id)
+
+    {
+      cadence: metadata[:cadence_id],
+      currency: 'usd',
+      actions: [build_modify_action(metadata[:subscription_id], new_pricing_plan_id, plan_version, lookup_key, quantity)]
+    }
+  end
+
+  def build_modify_action(subscription_id, plan_id, plan_version, lookup_key, quantity)
+    {
+      type: 'modify',
+      modify: {
+        type: 'pricing_plan_subscription_details',
+        pricing_plan_subscription_details: {
+          pricing_plan_subscription: subscription_id,
+          new_pricing_plan: plan_id,
+          new_pricing_plan_version: plan_version,
+          component_configurations: [{ lookup_key: lookup_key, quantity: quantity }]
+        }
+      }
+    }
+  end
+
+  def calculate_proration(old_plan_id:, new_plan_id:, old_quantity:, new_quantity:, next_billing_date:)
+    old_plan_price = Enterprise::Billing::V2::PlanCatalog.definition_for(old_plan_id)&.dig(:base_fee) || 0.0
+    new_plan_price = Enterprise::Billing::V2::PlanCatalog.definition_for(new_plan_id)&.dig(:base_fee) || 0.0
+
+    Enterprise::Billing::V2::ProrationCalculator.calculate(
+      old_plan_price: old_plan_price,
+      new_plan_price: new_plan_price,
+      old_quantity: old_quantity,
+      new_quantity: new_quantity,
+      next_billing_date: next_billing_date
+    )
+  end
+
+  def create_and_charge_invoice(line_items)
+    # Return success with no invoice if no line items (negligible proration)
+    return { success: true, amount: 0.0, message: 'No charges due to negligible proration' } if line_items.empty?
+
+    # Use common invoice payment service
+    payment_service = Enterprise::Billing::V2::InvoicePaymentService.new(account: account)
+    payment_service.create_and_pay_invoice(
+      line_items: line_items,
+      description: 'Proration charges for plan/seat changes',
+      metadata: {
+        account_id: account.id.to_s,
+        type: 'proration'
+      }
+    )
+  end
+
+  def update_account_plan(plan_id, quantity, next_billing_date)
+    plan_definition = Enterprise::Billing::V2::PlanCatalog.definition_for(plan_id)
+    plan_name = plan_definition&.dig(:display_name)
+
+    update_custom_attributes({
+                               'pricing_plan_id' => plan_id,
+                               'subscribed_quantity' => quantity,
+                               'plan_name' => plan_name,
+                               'next_billing_date' => next_billing_date
+                             })
+  end
+end

enterprise/app/services/enterprise/billing/v2/checkout_session_service.rb

@@ -0,0 +1,85 @@
+class Enterprise::Billing::V2::CheckoutSessionService < Enterprise::Billing::V2::BaseService
+  include Enterprise::Billing::Concerns::PlanFeatureManager
+  include Enterprise::Billing::Concerns::StripeV2ClientHelper
+
+  def create_subscription_checkout(pricing_plan_id:, quantity: 1)
+    @pricing_plan_id = pricing_plan_id
+    @quantity = quantity.to_i.positive? ? quantity.to_i : 1
+
+    base_url = ENV.fetch('FRONTEND_URL')
+    @success_url = "#{base_url}/app/accounts/#{@account.id}/settings/billing?session_id={CHECKOUT_SESSION_ID}"
+    @cancel_url = "#{base_url}/app/accounts/#{@account.id}/settings/billing"
+
+    validate_params
+    store_pending_subscription_quantity
+    session = create_checkout_session(checkout_session_params)
+    session.url
+  end
+
+  private
+
+  def validate_params
+    raise StandardError, I18n.t('errors.enterprise.billing.stripe_customer_required') if stripe_customer_id.blank?
+  end
+
+  def store_pending_subscription_quantity
+    # Store quantity in custom_attributes for webhook to use
+    # This is more reliable than extracting from subscription component_values
+    update_custom_attributes({
+                               'pending_subscription_quantity' => @quantity,
+                               'pending_subscription_pricing_plan' => @pricing_plan_id
+                             })
+  end
+
+  def checkout_session_params
+    {
+      customer: stripe_customer_id,
+      checkout_items: build_checkout_items,
+      automatic_tax: {
+        enabled: true
+      },
+      customer_update: {
+        address: 'auto',
+        shipping: 'auto'
+      },
+      success_url: @success_url,
+      cancel_url: @cancel_url,
+      metadata: session_metadata
+    }
+  end
+
+  def build_checkout_items
+    lookup_key = extract_license_lookup_key
+    raise StandardError, I18n.t('errors.enterprise.billing.lookup_key_not_found', pricing_plan_id: @pricing_plan_id) unless lookup_key
+
+    [
+      {
+        type: 'pricing_plan_subscription_item',
+        pricing_plan_subscription_item: {
+          pricing_plan: @pricing_plan_id,
+          component_configurations: {
+            lookup_key => {
+              type: 'license_fee_component',
+              license_fee_component: {
+                quantity: @quantity
+              }
+            }
+          }
+        }
+      }
+    ]
+  end
+
+  def extract_license_lookup_key
+    Enterprise::Billing::V2::PlanCatalog.lookup_key_for_plan(@pricing_plan_id)
+  end
+
+  def session_metadata
+    {
+      account_id: account.id,
+      pricing_plan_id: @pricing_plan_id,
+      quantity: @quantity,
+      billing_version: 'v2'
+    }
+  end
+end

enterprise/app/services/enterprise/billing/v2/credit_management_service.rb

@@ -0,0 +1,84 @@
+class Enterprise::Billing::V2::CreditManagementService < Enterprise::Billing::V2::BaseService
+  # Sync monthly response credits (resets on billing cycle with topup preservation)
+  def sync_monthly_response_credits(amount)
+    with_locked_account do
+      # Preserve topup credits but cap at remaining balance
+      preserved_topup = preserve_topup_on_reset(
+        current_topup: response_topup_credits,
+        new_monthly: amount,
+        current_usage: response_usage
+      )
+      update_response_credits(monthly: amount, topup: preserved_topup)
+    end
+  end
+
+  # Add topup credits for responses
+  def add_response_topup_credits(amount)
+    with_locked_account do
+      new_topup = response_topup_credits + amount
+      update_response_credits(topup: new_topup)
+    end
+  end
+
+  def fetch_credit_grants
+    return [] if stripe_customer_id.blank?
+
+    response = Stripe::Billing::CreditGrant.list(
+      { customer: stripe_customer_id, limit: 100 }
+    )
+
+    grants = response.data.map do |grant|
+      transform_credit_grant(grant)
+    end
+    grants.reject { |grant| grant[:credits].zero? }
+  rescue Stripe::StripeError => e
+    ChatwootExceptionTracker.new(e, account: account).capture_exception
+    []
+  end
+
+  private
+
+  # Preserve topup credits on monthly reset, capped at remaining balance
+  # Formula: min(current_topup, max(0, (new_monthly + current_topup) - current_usage))
+  def preserve_topup_on_reset(current_topup:, new_monthly:, current_usage:)
+    # Calculate remaining balance after usage
+    total_after_sync = new_monthly + current_topup
+    remaining_balance = [total_after_sync - current_usage, 0].max
+
+    # Cap topup at remaining balance to avoid over-crediting
+    [current_topup, remaining_balance].min
+  end
+
+  def transform_credit_grant(grant)
+    category = grant_attribute(grant, :category)
+    metadata = grant_attribute(grant, :metadata) || {}
+
+    {
+      id: grant_attribute(grant, :id),
+      name: grant_attribute(grant, :name),
+      credits: calculate_grant_credits(category, metadata),
+      category: category,
+      source: metadata['source'] || category,
+      effective_at: parse_timestamp(grant_attribute(grant, :effective_at)),
+      expires_at: parse_timestamp(grant_attribute(grant, :expires_at)),
+      voided_at: parse_timestamp(grant_attribute(grant, :voided_at)),
+      created_at: parse_timestamp(grant_attribute(grant, :created))
+    }
+  end
+
+  def grant_attribute(grant, key)
+    grant[key] || grant.public_send(key)
+  end
+
+  def calculate_grant_credits(category, metadata)
+    return metadata['credits'].to_i if category == 'paid' && metadata['credits']
+
+    0
+  end
+
+  def parse_timestamp(timestamp)
+    return nil unless timestamp
+
+    Time.zone.at(timestamp)
+  end
+end

enterprise/app/services/enterprise/billing/v2/invoice_payment_service.rb

@@ -0,0 +1,138 @@
+class Enterprise::Billing::V2::InvoicePaymentService < Enterprise::Billing::V2::BaseService
+  # Common service for creating invoices with line items and charging immediately
+  # Used by both TopupService and ChangePlanService
+  #
+  # @param line_items [Array<Hash>] Array of line items: [{ amount:, description:, metadata: }]
+  # @param description [String] Description for the invoice
+  # @param currency [String] Currency code (default: 'usd')
+  # @param metadata [Hash] Metadata for the invoice
+  # @return [Hash] { success:, invoice_id:, invoice_url:, amount:, status: }
+
+  # Validate that customer has a default payment method
+  # If no default is set but payment methods exist, automatically set the first one as default
+  # @return [Hash, nil] Returns error hash if validation fails, nil if success
+  def validate_payment_method
+    return { success: false, message: 'No Stripe customer ID found' } if stripe_customer_id.blank?
+
+    customer = Stripe::Customer.retrieve(stripe_customer_id)
+
+    if customer.invoice_settings.default_payment_method.nil? && customer.default_source.nil?
+      # No default payment method found - try to set one automatically
+      ensure_default_payment_method_result = ensure_default_payment_method(customer)
+      return ensure_default_payment_method_result unless ensure_default_payment_method_result.nil?
+    end
+
+    nil
+  rescue Stripe::StripeError => e
+    Rails.logger.error("Failed to check payment method: #{e.message}")
+    { success: false, message: "Error validating payment method: #{e.message}" }
+  end
+
+  # Ensure a default payment method is set for the customer
+  # If payment methods exist but none is default, set the first one as default
+  # @param customer [Stripe::Customer] The Stripe customer object
+  # @return [Hash, nil] Returns error hash if no payment methods exist, nil if default is set successfully
+  def ensure_default_payment_method(customer)
+    payment_methods = fetch_customer_payment_methods(customer.id)
+    return no_payment_methods_error if payment_methods.data.empty?
+
+    set_first_payment_method_as_default(customer.id, payment_methods.data.first)
+    nil
+  rescue Stripe::StripeError => e
+    Rails.logger.error("Failed to set default payment method: #{e.message}")
+    { success: false, message: "Error setting default payment method: #{e.message}" }
+  end
+
+  def fetch_customer_payment_methods(customer_id)
+    Stripe::PaymentMethod.list(customer: customer_id, limit: 100)
+  end
+
+  def no_payment_methods_error
+    {
+      success: false,
+      message: 'No payment methods found. Please add a payment method before making a purchase.'
+    }
+  end
+
+  def set_first_payment_method_as_default(customer_id, payment_method)
+    Stripe::Customer.update(
+      customer_id,
+      invoice_settings: { default_payment_method: payment_method.id }
+    )
+    Rails.logger.info("Automatically set payment method #{payment_method.id} as default for customer #{customer_id}")
+  end
+
+  # Create invoice with line items and charge immediately
+  #
+  # @param line_items [Array<Hash>] Line items: [{ amount: (cents), description:, metadata: }]
+  # @param description [String] Invoice description
+  # @param currency [String] Currency (default: 'usd')
+  # @param metadata [Hash] Invoice metadata
+  # @return [Hash] { success:, invoice_id:, invoice_url:, amount:, status: }
+  def create_and_pay_invoice(line_items:, description:, currency: 'usd', metadata: {})
+    invoice = create_invoice(stripe_customer_id, currency, description, metadata)
+    add_line_items_to_invoice(invoice.id, stripe_customer_id, line_items, currency)
+    finalize_and_pay_invoice(invoice.id)
+  rescue Stripe::StripeError => e
+    Rails.logger.error("Error creating invoice: #{e.message}")
+    { success: false, message: "Error creating invoice: #{e.message}" }
+  end
+
+  private
+
+  def create_invoice(customer_id, currency, description, metadata)
+    Stripe::Invoice.create({
+                             customer: customer_id,
+                             currency: currency,
+                             collection_method: 'charge_automatically',
+                             auto_advance: false,
+                             description: description,
+                             metadata: metadata.stringify_keys
+                           })
+  end
+
+  def add_line_items_to_invoice(invoice_id, customer_id, line_items, currency)
+    line_items.each do |item|
+      Stripe::InvoiceItem.create({
+                                   customer: customer_id,
+                                   amount: item[:amount],
+                                   currency: currency,
+                                   invoice: invoice_id,
+                                   description: item[:description],
+                                   metadata: (item[:metadata] || {}).stringify_keys
+                                 })
+    end
+  end
+
+  # Finalize invoice and pay it immediately
+  # @param invoice_id [String] Stripe invoice ID
+  # @return [Hash] { success:, invoice_id:, invoice_url:, amount:, status: }
+  def finalize_and_pay_invoice(invoice_id)
+    # Finalize the invoice
+    finalized_invoice = Stripe::Invoice.finalize_invoice(
+      invoice_id,
+      { auto_advance: false }
+    )
+
+    # Pay the invoice immediately if not already paid
+    if finalized_invoice.status == 'paid'
+      build_invoice_response(finalized_invoice)
+    else
+      paid_invoice = Stripe::Invoice.pay(invoice_id, {})
+      build_invoice_response(paid_invoice)
+    end
+  rescue Stripe::StripeError => e
+    Rails.logger.error("Error finalizing/paying invoice: #{e.message}")
+    { success: false, message: "Error processing payment: #{e.message}" }
+  end
+
+  def build_invoice_response(invoice)
+    {
+      success: true,
+      invoice_id: invoice.id,
+      invoice_url: invoice.hosted_invoice_url,
+      amount: invoice.total / 100.0,
+      status: invoice.status
+    }
+  end
+end

enterprise/app/services/enterprise/billing/v2/plan_catalog.rb

@@ -0,0 +1,107 @@
+module Enterprise::Billing::V2::PlanCatalog
+  DEFAULT_CURRENCY = 'usd'.freeze
+  CREDIT_UNIT = 'Credits'.freeze
+
+  PLAN_DEFINITIONS = [
+    {
+      key: :free,
+      display_name: 'Hacker',
+      base_fee: 0.0,
+      monthly_credits: 0,
+      config_key: 'STRIPE_HACKER_PLAN_ID',
+      licensed_item_lookup_key: 'chatwoot_hacker_license_fee_v2'
+    },
+    {
+      key: :startup,
+      display_name: 'Startups',
+      base_fee: 19.0,
+      monthly_credits: 300,
+      config_key: 'STRIPE_STARTUP_PLAN_ID',
+      licensed_item_lookup_key: 'chatwoot_startup_license_fee_v2'
+    },
+    {
+      key: :business,
+      display_name: 'Business',
+      base_fee: 39.0,
+      monthly_credits: 500,
+      config_key: 'STRIPE_BUSINESS_PLAN_ID',
+      licensed_item_lookup_key: 'chatwoot_business_license_fee_v2'
+    },
+    {
+      key: :enterprise,
+      display_name: 'Enterprise',
+      base_fee: 99.0,
+      monthly_credits: 800,
+      config_key: 'STRIPE_ENTERPRISE_PLAN_ID',
+      licensed_item_lookup_key: 'chatwoot_enterprise_license_fee_v2'
+    }
+  ].freeze
+
+  module_function
+
+  def plans
+    PLAN_DEFINITIONS.map do |definition|
+      plan_id = plan_id_for(definition)
+      build_plan(definition, plan_id)
+    end
+  end
+
+  def definition_for(plan_id)
+    PLAN_DEFINITIONS.each do |definition|
+      return definition if plan_id_for(definition) == plan_id
+    end
+    nil
+  end
+
+  def plan_id_for(definition)
+    InstallationConfig.find_by(name: definition[:config_key])&.value
+  end
+
+  def lookup_key_for_plan(plan_id)
+    # Returns the licensed_item_lookup_key for checkout sessions
+    definition = definition_for(plan_id)
+    definition&.dig(:licensed_item_lookup_key)
+  end
+
+  def build_plan(definition, plan_id)
+    {
+      id: plan_id,
+      display_name: definition[:display_name],
+      currency: DEFAULT_CURRENCY,
+      tax_behavior: 'exclusive',
+      components: build_components(definition)
+    }
+  end
+
+  def build_components(definition)
+    components = [service_action_component(definition), rate_card_component(definition)]
+    components << license_fee_component(definition) if definition[:base_fee]&.positive?
+    components
+  end
+
+  def service_action_component(definition)
+    {
+      type: 'service_action',
+      name: 'Monthly Credits',
+      credit_amount: definition[:monthly_credits],
+      credit_unit: CREDIT_UNIT
+    }
+  end
+
+  def rate_card_component(_definition)
+    {
+      type: 'rate_card',
+      name: 'Overage Rate',
+      rate_unit: CREDIT_UNIT,
+      meter_id: nil
+    }
+  end
+
+  def license_fee_component(definition)
+    {
+      type: 'license_fee',
+      name: 'Base Fee',
+      unit_amount: definition[:base_fee].round(2)
+    }
+  end
+end

enterprise/app/services/enterprise/billing/v2/proration_calculator.rb

@@ -0,0 +1,99 @@
+# rubocop:disable Style/ClassAndModuleChildren
+module Enterprise
+  module Billing
+    module V2
+      class ProrationCalculator
+        # Calculate prorated amounts for subscription changes
+        #
+        # @param old_plan_price [Float] Price per unit of the old plan
+        # @param new_plan_price [Float] Price per unit of the new plan
+        # @param old_quantity [Integer] Old quantity/seats
+        # @param new_quantity [Integer] New quantity/seats
+        # @param next_billing_date [String/Time] Next billing date (ISO 8601)
+        # @return [Hash] { credit_amount:, charge_amount:, net_amount:, days_remaining:, total_days: }
+        #
+        def self.calculate(old_plan_price:, new_plan_price:, old_quantity:, new_quantity:, next_billing_date:)
+          new(
+            old_plan_price: old_plan_price,
+            new_plan_price: new_plan_price,
+            old_quantity: old_quantity,
+            new_quantity: new_quantity,
+            next_billing_date: next_billing_date
+          ).calculate
+        end
+
+        def initialize(old_plan_price:, new_plan_price:, old_quantity:, new_quantity:, next_billing_date:)
+          @old_plan_price = old_plan_price.to_f
+          @new_plan_price = new_plan_price.to_f
+          @old_quantity = old_quantity.to_i
+          @new_quantity = new_quantity.to_i
+          @next_billing_date = parse_date(next_billing_date)
+          @current_date = Time.zone.now
+        end
+
+        def calculate
+          {
+            credit_amount: credit_amount,
+            charge_amount: charge_amount,
+            net_amount: net_amount,
+            days_remaining: days_remaining,
+            total_days: total_days,
+            proration_factor: proration_factor
+          }
+        end
+
+        private
+
+        def parse_date(date)
+          return date if date.is_a?(Time) || date.is_a?(DateTime)
+
+          Time.zone.parse(date.to_s)
+        rescue StandardError
+          raise ArgumentError, "Invalid next_billing_date format: #{date}"
+        end
+
+        # Credit from unused time on old plan
+        def credit_amount
+          @credit_amount ||= (@old_plan_price * @old_quantity * proration_factor).round(2)
+        end
+
+        # Charge for new plan for remaining time
+        def charge_amount
+          @charge_amount ||= (@new_plan_price * @new_quantity * proration_factor).round(2)
+        end
+
+        # Net amount to charge (positive) or credit (negative)
+        def net_amount
+          @net_amount ||= (charge_amount - credit_amount).round(2)
+        end
+
+        # Number of days remaining in current billing period
+        def days_remaining
+          @days_remaining ||= (@next_billing_date.to_date - @current_date.to_date).to_i
+        end
+
+        # Total days in the actual billing period (calculate from current cycle)
+        # This ensures proration factor never exceeds 1.0
+        def total_days
+          @total_days ||= begin
+            # Calculate the total days in this billing cycle
+            # Assume billing started one month ago from next_billing_date
+            billing_start = @next_billing_date - 1.month
+            ((@next_billing_date.to_date - billing_start.to_date).to_i)
+          end
+        end
+
+        # Fraction of billing period remaining
+        # This value should always be between 0.0 and 1.0
+        def proration_factor
+          @proration_factor ||= begin
+            factor = days_remaining.to_f / total_days
+            # Ensure factor never exceeds 1.0
+            [factor, 1.0].min.round(4)
+          end
+        end
+      end
+    end
+  end
+end
+# rubocop:enable Style/ClassAndModuleChildren

enterprise/app/services/enterprise/billing/v2/subscription_provisioning_service.rb

@@ -0,0 +1,120 @@
+class Enterprise::Billing::V2::SubscriptionProvisioningService < Enterprise::Billing::V2::BaseService
+  include Enterprise::Billing::Concerns::PlanFeatureManager
+  include Enterprise::Billing::Concerns::PlanProvisioningHelper
+  include Enterprise::Billing::Concerns::StripeV2ClientHelper
+
+  def provision(subscription_id:)
+    process_subscription(subscription_id)
+  end
+
+  def refresh
+    return if stripe_subscription_id.blank?
+
+    process_subscription(stripe_subscription_id)
+  end
+
+  private
+
+  def process_subscription(subscription_id)
+    # Retrieve pricing plan subscription details from Stripe V2 API
+    subscription = retrieve_pricing_plan_subscription(subscription_id)
+
+    # Check if subscription is canceled
+    if servicing_status(subscription) == 'canceled'
+      cancel_subscription
+      reset_captain_usage
+      return { pricing_plan_id: nil, quantity: nil }
+    end
+
+    # Extract details from the subscription
+    pricing_plan_id = extract_pricing_plan_id(subscription)
+    quantity = extract_subscription_quantity(subscription)
+    billing_cadence = extract_billing_cadence(subscription)
+
+    # Update account with subscription details
+    update_subscription_details(subscription_id, pricing_plan_id, quantity, billing_cadence)
+
+    # Provision the subscription: sync credits and enable features
+    provision_new_plan(pricing_plan_id) if pricing_plan_id.present?
+
+    # Reset usage for the new billing cycle
+    reset_captain_usage
+
+    { pricing_plan_id: pricing_plan_id, quantity: quantity }
+  end
+
+  def servicing_status(subscription_plan)
+    extract_attribute(subscription_plan, :servicing_status)
+  end
+
+  def cancel_subscription
+    hacker_plan_config = InstallationConfig.find_by(name: 'STRIPE_HACKER_PLAN_ID')
+    return if hacker_plan_config.nil?
+
+    pricing_plan_id = hacker_plan_config.value
+
+    # Update subscription status and plan details
+    attributes = {
+      'plan_name': 'Hacker',
+      'stripe_pricing_plan_id': pricing_plan_id,
+      'subscribed_quantity': 2,
+      'stripe_subscription_id': nil,
+      'billing_cadence': nil,
+      'subscription_status': 'canceled'
+    }
+    update_custom_attributes(attributes)
+
+    # Sync credits for Hacker plan (0 credits)
+    Enterprise::Billing::V2::CreditManagementService
+      .new(account: account)
+      .sync_monthly_response_credits(0)
+
+    # Disable all premium features and save
+    disable_all_premium_features
+    account.save!
+  end
+
+  def extract_pricing_plan_id(subscription)
+    extract_attribute(subscription, :pricing_plan)
+  end
+
+  def extract_billing_cadence(subscription)
+    extract_attribute(subscription, :billing_cadence)
+  end
+
+  def extract_subscription_quantity(_subscription)
+    # Get quantity from account custom_attributes (set during checkout)
+    pending_quantity = custom_attribute('pending_subscription_quantity')
+    return pending_quantity.to_i if pending_quantity.present? && pending_quantity.to_i.positive?
+
+    return subscribed_quantity if subscribed_quantity.positive?
+
+    1
+  end
+
+  def update_subscription_details(subscription_id, pricing_plan_id, quantity, billing_cadence)
+    Rails.logger.info "[V2 Billing] Updating subscription details: subscription_id=#{subscription_id}, " \
+                      "pricing_plan_id=#{pricing_plan_id}, quantity=#{quantity}"
+
+    attributes = {
+      'stripe_subscription_id' => subscription_id,
+      'subscribed_quantity' => quantity,
+      'subscription_status' => 'active',
+      'pending_subscription_quantity' => nil,
+      'pending_subscription_pricing_plan' => nil,
+      'billing_cadence' => billing_cadence,
+      'next_billing_date' => nil,
+      'pending_stripe_pricing_plan_id' => nil,
+      'stripe_billing_version' => 2
+    }
+    attributes['stripe_pricing_plan_id'] = pricing_plan_id if pricing_plan_id.present?
+
+    # Add plan name from catalog
+    if pricing_plan_id.present?
+      plan_definition = Enterprise::Billing::V2::PlanCatalog.definition_for(pricing_plan_id)
+      attributes['plan_name'] = plan_definition[:display_name] if plan_definition
+    end
+
+    update_custom_attributes(attributes)
+  end
+end

enterprise/app/services/enterprise/billing/v2/topup_catalog.rb

@@ -0,0 +1,34 @@
+module Enterprise::Billing::V2::TopupCatalog
+  DEFAULT_TOPUPS = [
+    { credits: 1000, amount: 20.0 },
+    { credits: 2000, amount: 40.0 },
+    { credits: 3000, amount: 60.0 },
+    { credits: 4000, amount: 80.0 }
+  ].freeze
+
+  module_function
+
+  def options
+    custom_options = InstallationConfig.find_by(name: 'STRIPE_TOPUP_OPTIONS')&.value
+    parsed = parse_options(custom_options)
+    (parsed.presence || DEFAULT_TOPUPS).sort_by { |opt| opt[:credits] }.map do |option|
+      {
+        credits: option[:credits],
+        amount: option[:amount],
+        currency: option[:currency] || 'usd'
+      }
+    end
+  end
+
+  def parse_options(raw)
+    return [] if raw.blank?
+
+    JSON.parse(raw, symbolize_names: true)
+  rescue JSON::ParserError
+    []
+  end
+
+  def find_option(credits)
+    options.find { |option| option[:credits].to_i == credits.to_i }
+  end
+end

enterprise/app/services/enterprise/billing/v2/topup_service.rb

@@ -0,0 +1,145 @@
+class Enterprise::Billing::V2::TopupService < Enterprise::Billing::V2::BaseService
+  def create_topup(credits:)
+    validation_result = validate_topup_request(credits)
+    return validation_result unless validation_result[:valid]
+
+    topup_definition = validation_result[:topup_definition]
+    amount_cents = (topup_definition[:amount] * 100).to_i
+    currency = topup_definition[:currency] || 'usd'
+
+    with_locked_account do
+      process_topup_transaction(credits, amount_cents, currency, topup_definition[:amount])
+    end
+  rescue Stripe::StripeError => e
+    { success: false, message: "Stripe error: #{e.message}" }
+  end
+
+  private
+
+  def validate_topup_request(credits)
+    return { valid: false, success: false, message: 'Invalid topup amount' } unless credits.to_i.positive?
+
+    plan_validation = validate_subscription_plan
+    return plan_validation unless plan_validation[:valid]
+
+    topup_definition = Enterprise::Billing::V2::TopupCatalog.find_option(credits)
+    return { valid: false, success: false, message: 'Unsupported topup amount' } unless topup_definition
+    return { valid: false, success: false, message: 'Stripe customer not configured' } if stripe_customer_id.blank?
+
+    payment_service = Enterprise::Billing::V2::InvoicePaymentService.new(account: account)
+    payment_method_validation = payment_service.validate_payment_method
+    return payment_method_validation.merge(valid: false) if payment_method_validation
+
+    { valid: true, topup_definition: topup_definition }
+  end
+
+  def validate_subscription_plan
+    plan_name = custom_attribute('plan_name')
+
+    # Block topup if no plan or on Hacker plan
+    if plan_name.blank? || plan_name.downcase == 'hacker'
+      return {
+        valid: false,
+        success: false,
+        message: 'Top-ups are only available for Startup, Business, and Enterprise plans. Please upgrade your plan to purchase credits.'
+      }
+    end
+
+    { valid: true }
+  end
+
+  def process_topup_transaction(credits, amount_cents, currency, amount)
+    line_items = build_topup_line_items(credits, amount_cents)
+    invoice_result = charge_topup_invoice(line_items, currency)
+    return invoice_result unless invoice_result[:success]
+
+    credit_grant = create_stripe_credit_grant(amount_cents, currency, credits)
+    return { success: false, message: 'Failed to create credit grant in Stripe' } unless credit_grant
+
+    build_success_response(credits, amount, currency, invoice_result[:invoice_id], credit_grant['id'])
+  end
+
+  def build_topup_line_items(credits, amount_cents)
+    [{
+      amount: amount_cents,
+      description: "Credit Topup: #{credits} credits",
+      metadata: {
+        account_id: account.id.to_s,
+        credits: credits.to_s,
+        topup: 'true'
+      }
+    }]
+  end
+
+  def charge_topup_invoice(line_items, currency)
+    payment_service = Enterprise::Billing::V2::InvoicePaymentService.new(account: account)
+    payment_service.create_and_pay_invoice(
+      line_items: line_items,
+      description: 'Credit top-up purchase',
+      currency: currency,
+      metadata: {
+        account_id: account.id.to_s,
+        topup: 'true'
+      }
+    )
+  end
+
+  def build_success_response(credits, amount, currency, invoice_id, credit_grant_id)
+    {
+      success: true,
+      message: 'Top-up purchased successfully',
+      credits: credits,
+      amount: amount,
+      currency: currency,
+      invoice_id: invoice_id,
+      credit_grant_id: credit_grant_id
+    }
+  end
+
+  # Create Credit Grant in Stripe using monetary amount (not custom_pricing_unit)
+  # Following Stripe UBB Integration Guide section 8
+  def create_stripe_credit_grant(amount_cents, currency, credits)
+    Stripe::Billing::CreditGrant.create(
+      credit_grant_params(amount_cents, currency, credits)
+    )
+  end
+
+  def credit_grant_params(amount_cents, currency, credits)
+    {
+      customer: stripe_customer_id,
+      name: "Topup: #{credits} credits",
+      amount: credit_grant_amount(amount_cents, currency),
+      applicability_config: credit_grant_applicability,
+      category: 'paid',
+      metadata: credit_grant_metadata(credits)
+    }
+  end
+
+  def credit_grant_amount(amount_cents, currency)
+    {
+      type: 'monetary',
+      monetary: {
+        currency: currency,
+        value: amount_cents
+      }
+    }
+  end
+
+  def credit_grant_applicability
+    # Apply credit grant to all metered usage for this customer
+    # This ensures topup credits offset meter-based billing
+    {
+      scope: {
+        price_type: 'metered'
+      }
+    }
+  end
+
+  def credit_grant_metadata(credits)
+    {
+      account_id: account.id.to_s,
+      source: 'topup',
+      credits: credits.to_s
+    }
+  end
+end

enterprise/app/services/enterprise/billing/v2/usage_reporter_service.rb

@@ -0,0 +1,35 @@
+class Enterprise::Billing::V2::UsageReporterService < Enterprise::Billing::V2::BaseService
+  def report(credits_used, _feature = nil)
+    return { success: false, message: 'Missing Stripe configuration' } unless valid_configuration?
+
+    event = Stripe::Billing::MeterEvent.create(
+      meter_event_params(credits_used),
+      stripe_api_options
+    )
+
+    { success: true, event_id: event.identifier }
+  rescue Stripe::StripeError => e
+    { success: false, message: e.message }
+  end
+
+  private
+
+  def valid_configuration?
+    stripe_customer_id.present?
+  end
+
+  def meter_event_params(credits_used)
+    {
+      event_name: 'chatwoot.usage',
+      payload: {
+        value: credits_used.to_s,
+        stripe_customer_id: stripe_customer_id
+      },
+      identifier: "#{account.id}_#{Time.current.to_i}_#{SecureRandom.hex(4)}"
+    }
+  end
+
+  def stripe_api_options
+    { api_key: ENV.fetch('STRIPE_SECRET_KEY', nil), stripe_version: '2025-08-27.preview' }
+  end
+end

enterprise/app/services/enterprise/billing/v2/webhook_handler_service.rb

@@ -0,0 +1,57 @@
+class Enterprise::Billing::V2::WebhookHandlerService
+  include Enterprise::Billing::Concerns::StripeV2ClientHelper
+
+  def perform(event:)
+    @event = event
+    raise StandardError, 'Event is required' if @event.blank?
+    raise StandardError, 'Account not found' if account.blank?
+
+    case @event.type
+    when 'v2.billing.pricing_plan_subscription.servicing_activated'
+      Rails.logger.info "Handling subscription servicing activated event: #{@event.related_object.id}"
+      handle_subscription_servicing_activated(@event.related_object.id)
+    when 'v2.billing.cadence.billed'
+      Rails.logger.info "Handling cadence billed event: #{@event.related_object.id}"
+      refresh_account_subscription_details(@event.related_object.id)
+    end
+  rescue StandardError => e
+    ChatwootExceptionTracker.new(e, account: account).capture_exception
+    raise
+  end
+
+  private
+
+  def account
+    @account ||= begin
+      related_object = @event.related_object
+      subscription_id = related_object.id
+
+      customer_id = fetch_customer_id_from_subscription(subscription_id)
+      found_account = Account.find_by("custom_attributes->>'stripe_customer_id' = ?", customer_id) if customer_id.present?
+
+      Rails.logger.warn "Could not find account for subscription #{subscription_id}" if found_account.blank?
+
+      found_account
+    end
+  end
+
+  def fetch_customer_id_from_subscription(subscription_id)
+    subscription = retrieve_pricing_plan_subscription(subscription_id)
+    return nil unless subscription&.billing_cadence
+
+    cadence = retrieve_billing_cadence(subscription.billing_cadence)
+    cadence.payer&.customer
+  end
+
+  def handle_subscription_servicing_activated(subscription_id)
+    Enterprise::Billing::V2::SubscriptionProvisioningService
+      .new(account: account)
+      .provision(subscription_id: subscription_id)
+  end
+
+  def refresh_account_subscription_details(_cadence_id)
+    Enterprise::Billing::V2::SubscriptionProvisioningService
+      .new(account: account)
+      .refresh
+  end
+end

spec/enterprise/controllers/enterprise/api/v1/accounts_controller_spec.rb

@@ -205,8 +205,10 @@ RSpec.describe 'Enterprise Billing APIs', type: :request do
               },
               'conversation' => {},
               'captain' => {
-                'documents' => { 'consumed' => 0, 'current_available' => ChatwootApp.max_limit, 'total_count' => ChatwootApp.max_limit },
+                'documents' => { 'consumed' => 0, 'current_available' => ChatwootApp.max_limit, 'total_count' => ChatwootApp.max_limit,
-                'responses' => { 'consumed' => 0, 'current_available' => ChatwootApp.max_limit, 'total_count' => ChatwootApp.max_limit }
+                                 'monthly' => nil, 'topup' => nil },
+                'responses' => { 'consumed' => 0, 'current_available' => ChatwootApp.max_limit, 'total_count' => ChatwootApp.max_limit,
+                                 'monthly' => 0, 'topup' => 0 }
               },
               'non_web_inboxes' => {}
             }

spec/enterprise/controllers/enterprise/webooks/stripe_controller_spec.rb

@@ -2,24 +2,34 @@ require 'rails_helper'
 
 RSpec.describe 'Enterprise::Webhooks::StripeController', type: :request do
   describe 'POST /enterprise/webhooks/stripe' do
-    let(:params) { { content: 'hello' } }
+    let(:payload) { { type: 'customer.subscription.updated', content: 'hello' }.to_json }
+    let(:event_object) { instance_double(Stripe::Event, type: 'customer.subscription.updated') }
+
+    around do |example|
+      ENV['STRIPE_WEBHOOK_SECRET'] = 'test_secret'
+      ENV['STRIPE_WEBHOOK_SECRET_V2'] = 'test_secret_v2'
+      example.run
+      ENV.delete('STRIPE_WEBHOOK_SECRET')
+      ENV.delete('STRIPE_WEBHOOK_SECRET_V2')
+    end
 
     it 'call the Enterprise::Billing::HandleStripeEventService with the params' do
       handle_stripe = double
-      allow(Stripe::Webhook).to receive(:construct_event).and_return(params)
+      allow(Stripe::Webhook).to receive(:construct_event).and_return(event_object)
       allow(Enterprise::Billing::HandleStripeEventService).to receive(:new).and_return(handle_stripe)
       allow(handle_stripe).to receive(:perform)
-      post '/enterprise/webhooks/stripe', headers: { 'Stripe-Signature': 'test' }, params: params
+      post '/enterprise/webhooks/stripe', params: payload, headers: { 'Content-Type' => 'application/json', 'Stripe-Signature' => 'test' }
-      expect(handle_stripe).to have_received(:perform).with(event: params)
+      expect(handle_stripe).to have_received(:perform).with(event: event_object)
     end
 
     it 'returns a bad request if the headers are missing' do
-      post '/enterprise/webhooks/stripe', params: params
+      post '/enterprise/webhooks/stripe', params: payload, headers: { 'Content-Type' => 'application/json' }
       expect(response).to have_http_status(:bad_request)
     end
 
     it 'returns a bad request if the headers are invalid' do
-      post '/enterprise/webhooks/stripe', headers: { 'Stripe-Signature': 'test' }, params: params
+      allow(Stripe::Webhook).to receive(:construct_event).and_raise(Stripe::SignatureVerificationError.new('Invalid signature', 'sig'))
+      post '/enterprise/webhooks/stripe', params: payload, headers: { 'Content-Type' => 'application/json', 'Stripe-Signature' => 'test' }
       expect(response).to have_http_status(:bad_request)
     end
   end

spec/enterprise/jobs/enterprise/billing/credit_sync_job_spec.rb

@@ -0,0 +1,59 @@
+require 'rails_helper'
+
+RSpec.describe Enterprise::Billing::CreditSyncJob, type: :job do
+  include ActiveJob::TestHelper
+
+  before do
+    allow(ENV).to receive(:fetch).and_call_original
+    allow(ENV).to receive(:fetch).with('STRIPE_SECRET_KEY', nil).and_return('sk_test_123')
+    allow(InstallationConfig).to receive(:find_by).and_call_original
+    allow(InstallationConfig).to receive(:find_by).with(name: 'STRIPE_METER_ID')
+                                                  .and_return(instance_double(InstallationConfig, value: 'mtr_test_123'))
+  end
+
+  describe '#perform' do
+    context 'with no arguments' do
+      let!(:account) do
+        create(:account, custom_attributes: {
+                 'stripe_customer_id' => 'cus_123',
+                 'stripe_billing_version' => 2,
+                 'captain_responses_usage' => 100,
+                 'stripe_last_synced_credits' => 50
+               })
+      end
+
+      it 'syncs all accounts with Stripe customer ID' do
+        usage_reporter = instance_double(Enterprise::Billing::V2::UsageReporterService)
+        allow(Enterprise::Billing::V2::UsageReporterService).to receive(:new).and_return(usage_reporter)
+        allow(usage_reporter).to receive(:report).with(50).and_return({ success: true, event_id: 'evt_123' })
+
+        result = described_class.new.perform
+
+        expect(result).to eq({ synced: 1, failed: 0 })
+        expect(account.reload.custom_attributes['stripe_last_synced_credits']).to eq(100)
+      end
+    end
+
+    context 'with account argument' do
+      let(:account) do
+        create(:account, custom_attributes: {
+                 'stripe_customer_id' => 'cus_123',
+                 'captain_responses_usage' => 100,
+                 'stripe_last_synced_credits' => 30
+               })
+      end
+
+      it 'syncs single account' do
+        usage_reporter = instance_double(Enterprise::Billing::V2::UsageReporterService)
+        allow(Enterprise::Billing::V2::UsageReporterService).to receive(:new).and_return(usage_reporter)
+        allow(usage_reporter).to receive(:report).and_return({ success: true, event_id: 'evt_123' })
+
+        result = described_class.new.perform(account)
+
+        expect(result[:success]).to be true
+        expect(result[:credits_reported]).to eq(70)
+        expect(account.reload.custom_attributes['stripe_last_synced_credits']).to eq(100)
+      end
+    end
+  end
+end

spec/enterprise/services/enterprise/billing/create_stripe_customer_service_spec.rb

@@ -1,139 +1,99 @@
 require 'rails_helper'
 
 describe Enterprise::Billing::CreateStripeCustomerService do
-  subject(:create_stripe_customer_service) { described_class }
+  subject(:service) { described_class.new(account: account) }
 
   let(:account) { create(:account) }
-  let!(:admin1) { create(:user, account: account, role: :administrator) }
+  let!(:admin) { create(:user, account: account, role: :administrator) }
-  let(:admin2) { create(:user, account: account, role: :administrator) }
+  let(:stripe_customer_double) { instance_double(Stripe::Customer, id: 'cus_new') }
-  let(:subscriptions_list) { double }
+  let(:subscriptions_list) { Stripe::ListObject.construct_from({ data: [] }) }
+  let(:hacker_plan_id) { 'price_hacker_random' }
 
-  describe '#perform' do
+  before do
-    before do
+    create(
-      create(
+      :installation_config,
-        :installation_config,
+      name: 'CHATWOOT_CLOUD_PLANS',
-        { name: 'CHATWOOT_CLOUD_PLANS', value: [
+      value: [
-          { 'name' => 'A Plan Name', 'product_id' => ['prod_hacker_random'], 'price_ids' => ['price_hacker_random'] }
-        ] }
-      )
-    end
-
-    it 'does not call stripe methods if customer id is present' do
-      account.update!(custom_attributes: { stripe_customer_id: 'cus_random_number' })
-      allow(subscriptions_list).to receive(:data).and_return([])
-      allow(Stripe::Customer).to receive(:create)
-      allow(Stripe::Subscription).to receive(:list).and_return(subscriptions_list)
-      allow(Stripe::Subscription).to receive(:create)
-        .and_return(
-          {
-            plan: { id: 'price_random_number', product: 'prod_random_number' },
-            quantity: 2
-          }.with_indifferent_access
-        )
-
-      create_stripe_customer_service.new(account: account).perform
-
-      expect(Stripe::Customer).not_to have_received(:create)
-      expect(Stripe::Subscription)
-        .to have_received(:create)
-        .with({ customer: 'cus_random_number', items: [{ price: 'price_hacker_random', quantity: 2 }] })
-
-      expect(account.reload.custom_attributes).to eq(
         {
-          stripe_customer_id: 'cus_random_number',
+          'name' => 'Hacker',
-          stripe_price_id: 'price_random_number',
+          'limits' => {
-          stripe_product_id: 'prod_random_number',
+            'captain_responses_monthly' => 5,
-          subscribed_quantity: 2,
+            'captain_responses_topup' => 0
-          plan_name: 'A Plan Name'
+          }
-        }.with_indifferent_access
+        }
-      )
+      ]
-    end
+    )
 
-    it 'calls stripe methods to create a customer and updates the account' do
+    create(:installation_config, name: 'STRIPE_HACKER_PLAN_ID', value: hacker_plan_id)
-      customer = double
-      allow(Stripe::Customer).to receive(:create).and_return(customer)
-      allow(customer).to receive(:id).and_return('cus_random_number')
-      allow(Stripe::Subscription)
-        .to receive(:create)
-        .and_return(
-          {
-            plan: { id: 'price_random_number', product: 'prod_random_number' },
-            quantity: 2
-          }.with_indifferent_access
-        )
-
-      create_stripe_customer_service.new(account: account).perform
-
-      expect(Stripe::Customer).to have_received(:create).with({ name: account.name, email: admin1.email })
-      expect(Stripe::Subscription)
-        .to have_received(:create)
-        .with({ customer: customer.id, items: [{ price: 'price_hacker_random', quantity: 2 }] })
-
-      expect(account.reload.custom_attributes).to eq(
-        {
-          stripe_customer_id: customer.id,
-          stripe_price_id: 'price_random_number',
-          stripe_product_id: 'prod_random_number',
-          subscribed_quantity: 2,
-          plan_name: 'A Plan Name'
-        }.with_indifferent_access
-      )
-    end
   end
 
-  describe 'when checking for existing subscriptions' do
+  describe '#perform' do
-    before do
+    context 'when account already has an active subscription' do
-      create(
-        :installation_config,
-        { name: 'CHATWOOT_CLOUD_PLANS', value: [
-          { 'name' => 'A Plan Name', 'product_id' => ['prod_hacker_random'], 'price_ids' => ['price_hacker_random'] }
-        ] }
-      )
-    end
-
-    context 'when account has no stripe_customer_id' do
-      it 'creates a new subscription' do
-        customer = double
-        allow(Stripe::Customer).to receive(:create).and_return(customer)
-        allow(customer).to receive(:id).and_return('cus_random_number')
-        allow(Stripe::Subscription).to receive(:create).and_return(
-          {
-            plan: { id: 'price_random_number', product: 'prod_random_number' },
-            quantity: 2
-          }.with_indifferent_access
-        )
-
-        create_stripe_customer_service.new(account: account).perform
-
-        expect(Stripe::Customer).to have_received(:create)
-        expect(Stripe::Subscription).to have_received(:create)
-      end
-    end
-
-    context 'when account has stripe_customer_id' do
-      let(:stripe_customer_id) { 'cus_random_number' }
-
       before do
-        account.update!(custom_attributes: { stripe_customer_id: stripe_customer_id })
+        account.update!(custom_attributes: { stripe_customer_id: 'cus_existing' })
+        allow(Stripe::Subscription).to receive(:list)
+          .and_return(Stripe::ListObject.construct_from({ data: ['subscription'] }))
       end
 
-      context 'when customer has active subscriptions' do
+      it 'returns without modifying the account or contacting Stripe' do
+        expect(Stripe::Customer).not_to receive(:create)
+
+        expect { service.perform }.not_to(change { account.reload.custom_attributes })
+      end
+    end
+
+    context 'when v2 billing configuration is missing' do
+      before do
+        InstallationConfig.find_by(name: 'STRIPE_HACKER_PLAN_ID').destroy!
+      end
+
+      it 'raises an informative error' do
+        expect { service.perform }.to raise_error(
+          StandardError,
+          'V2 billing configuration is required. Please configure STRIPE_HACKER_PLAN_ID.'
+        )
+      end
+    end
+
+    context 'when account needs to be upgraded to v2 billing' do
+      context 'when stripe customer already exists' do
         before do
+          account.update!(custom_attributes: { stripe_customer_id: 'cus_existing' })
           allow(Stripe::Subscription).to receive(:list).and_return(subscriptions_list)
-          allow(subscriptions_list).to receive(:data).and_return(['subscription'])
+          allow(Stripe::Customer).to receive(:create)
-          allow(Stripe::Subscription).to receive(:create)
         end
 
-        it 'does not create a new subscription' do
+        it 'does not create a new customer but updates custom attributes for v2 billing' do
-          create_stripe_customer_service.new(account: account).perform
+          service.perform
 
-          expect(Stripe::Subscription).not_to have_received(:create)
+          expect(Stripe::Customer).not_to have_received(:create)
-          expect(Stripe::Subscription).to have_received(:list).with(
+
-            {
+          expect(account.reload.custom_attributes).to include(
-              customer: stripe_customer_id,
+            'stripe_customer_id' => 'cus_existing',
-              status: 'active',
+            'stripe_pricing_plan_id' => hacker_plan_id,
-              limit: 1
+            'plan_name' => 'Hacker',
-            }
+            'subscribed_quantity' => described_class::DEFAULT_QUANTITY,
+            'stripe_billing_version' => 2
+          )
+        end
+      end
+
+      context 'when stripe customer does not exist' do
+        before do
+          allow(Stripe::Customer).to receive(:create).and_return(stripe_customer_double)
+        end
+
+        it 'creates a stripe customer and updates the account with v2 billing attributes' do
+          service.perform
+
+          expect(Stripe::Customer).to have_received(:create).with({ name: account.name, email: admin.email })
+
+          expect(account.reload.custom_attributes).to include(
+            'stripe_customer_id' => 'cus_new',
+            'stripe_pricing_plan_id' => hacker_plan_id,
+            'plan_name' => 'Hacker',
+            'subscribed_quantity' => described_class::DEFAULT_QUANTITY,
+            'stripe_billing_version' => 2
           )
         end
       end

spec/enterprise/services/enterprise/billing/handle_stripe_event_service_spec.rb

@@ -317,4 +317,146 @@ describe Enterprise::Billing::HandleStripeEventService do
       end
     end
   end
+
+  describe 'credit grant handling' do
+    let(:credit_service) { instance_double(Enterprise::Billing::V2::CreditManagementService) }
+
+    before do
+      allow(Enterprise::Billing::V2::CreditManagementService).to receive(:new)
+        .with(account: account).and_return(credit_service)
+    end
+
+    context 'when handling monthly credit grant' do
+      it 'adds credits from Stripe' do
+        allow(credit_service).to receive(:sync_monthly_response_credits)
+
+        # Webhook event object (minimal, just has ID)
+        grant_event_object = OpenStruct.new(
+          id: 'credgr_test_123',
+          customer: 'cus_123'
+        )
+        allow(event).to receive(:type).and_return('billing.credit_grant.created')
+        allow(data).to receive(:object).and_return(grant_event_object)
+
+        # Full grant object from API (has complete amount structure)
+        api_grant_response = OpenStruct.new(
+          id: 'credgr_test_123',
+          customer: 'cus_123',
+          metadata: { 'credits' => '2000' },
+          amount: OpenStruct.new(
+            type: 'custom_pricing_unit',
+            custom_pricing_unit: OpenStruct.new(value: 2000)
+          ),
+          expires_at: Time.current
+        )
+        allow(Stripe::Billing::CreditGrant).to receive(:retrieve)
+          .with('credgr_test_123')
+          .and_return(api_grant_response)
+
+        stripe_event_service.new.perform(event: event)
+
+        expect(credit_service).to have_received(:sync_monthly_response_credits).with(2000)
+      end
+    end
+
+    context 'when handling topup credit grant' do
+      it 'adds topup credits' do
+        allow(credit_service).to receive(:sync_monthly_response_credits)
+
+        # Webhook event object (minimal, just has ID)
+        grant_event_object = OpenStruct.new(
+          id: 'credgr_test_456',
+          customer: 'cus_123'
+        )
+        allow(event).to receive(:type).and_return('billing.credit_grant.created')
+        allow(data).to receive(:object).and_return(grant_event_object)
+
+        # Full grant object from API (has complete amount structure)
+        api_grant_response = OpenStruct.new(
+          id: 'credgr_test_456',
+          customer: 'cus_123',
+          metadata: { 'credits' => '500' },
+          amount: OpenStruct.new(
+            type: 'custom_pricing_unit',
+            custom_pricing_unit: OpenStruct.new(value: 500)
+          ),
+          expires_at: nil
+        )
+        allow(Stripe::Billing::CreditGrant).to receive(:retrieve)
+          .with('credgr_test_456')
+          .and_return(api_grant_response)
+
+        stripe_event_service.new.perform(event: event)
+
+        expect(credit_service).to have_received(:sync_monthly_response_credits).with(500)
+      end
+    end
+
+    context 'when handling monetary type credit grant' do
+      it 'adds credits from monetary grant' do
+        allow(credit_service).to receive(:add_response_topup_credits)
+
+        # Webhook event object (minimal, just has ID)
+        grant_event_object = OpenStruct.new(
+          id: 'credgr_test_monetary',
+          customer: 'cus_123'
+        )
+        allow(event).to receive(:type).and_return('billing.credit_grant.created')
+        allow(data).to receive(:object).and_return(grant_event_object)
+
+        # Full grant object from API with monetary amount
+        api_grant_response = OpenStruct.new(
+          id: 'credgr_test_monetary',
+          customer: 'cus_123',
+          metadata: { 'credits' => '1000' },
+          amount: OpenStruct.new(
+            type: 'monetary',
+            monetary: OpenStruct.new(
+              currency: 'usd',
+              value: 1000
+            )
+          ),
+          expires_at: Time.current
+        )
+        allow(Stripe::Billing::CreditGrant).to receive(:retrieve)
+          .with('credgr_test_monetary')
+          .and_return(api_grant_response)
+
+        stripe_event_service.new.perform(event: event)
+
+        expect(credit_service).to have_received(:add_response_topup_credits).with(1000)
+      end
+    end
+
+    context 'when handling credit grant with zero amount' do
+      it 'does not call credit service' do
+        # Webhook event object (minimal, just has ID)
+        grant_event_object = OpenStruct.new(
+          id: 'credgr_test_zero',
+          customer: 'cus_123'
+        )
+        allow(event).to receive(:type).and_return('billing.credit_grant.created')
+        allow(data).to receive(:object).and_return(grant_event_object)
+
+        # Full grant object from API with zero amount
+        api_grant_response = OpenStruct.new(
+          id: 'credgr_test_zero',
+          customer: 'cus_123',
+          amount: OpenStruct.new(
+            type: 'custom_pricing_unit',
+            custom_pricing_unit: OpenStruct.new(value: 0)
+          ),
+          expires_at: Time.current
+        )
+        allow(Stripe::Billing::CreditGrant).to receive(:retrieve)
+          .with('credgr_test_zero')
+          .and_return(api_grant_response)
+
+        stripe_event_service.new.perform(event: event)
+
+        # Ensure we don't accidentally call these methods
+        expect(Enterprise::Billing::V2::CreditManagementService).not_to have_received(:new)
+      end
+    end
+  end
 end