diff --git a/app/controllers/dashboard_controller.rb b/app/controllers/dashboard_controller.rb
index 8aa7ed34a..d81b4c9da 100644
--- a/app/controllers/dashboard_controller.rb
+++ b/app/controllers/dashboard_controller.rb
@@ -35,6 +35,7 @@ class DashboardController < ActionController::Base
       'HCAPTCHA_SITE_KEY',
       'LOGOUT_REDIRECT_LINK',
       'DISABLE_USER_PROFILE_UPDATE',
+      'DEPLOYMENT_ENV',
       'INSTALLATION_PRICING_PLAN'
     ).merge(app_config)
   end
@@ -70,7 +71,6 @@ class DashboardController < ActionController::Base
       WHATSAPP_CONFIGURATION_ID: GlobalConfigService.load('WHATSAPP_CONFIGURATION_ID', ''),
       IS_ENTERPRISE: ChatwootApp.enterprise?,
       AZURE_APP_ID: GlobalConfigService.load('AZURE_APP_ID', ''),
-      DEPLOYMENT_ENV: GlobalConfigService.load('DEPLOYMENT_ENV', 'self-hosted'),
       GIT_SHA: GIT_HASH
     }
   end
diff --git a/app/models/account.rb b/app/models/account.rb
index ae7d570ee..a8eaa04ff 100644
--- a/app/models/account.rb
+++ b/app/models/account.rb
@@ -108,7 +108,6 @@ class Account < ApplicationRecord
 
   before_validation :validate_limit_keys
   after_create_commit :notify_creation
-  after_create :initialize_v2_billing
   after_destroy :remove_account_sequences
 
   def agents
@@ -166,16 +165,6 @@ class Account < ApplicationRecord
     Rails.configuration.dispatcher.dispatch(ACCOUNT_CREATED, Time.zone.now, account: self)
   end
 
-  def initialize_v2_billing
-    # Initialize V2 billing for Chatwoot Cloud accounts
-    return unless ChatwootApp.chatwoot_cloud?
-
-    # Set stripe_billing_version to 2 for all new accounts
-    # rubocop:disable Rails/SkipsModelValidations
-    update_columns(custom_attributes: (custom_attributes || {}).merge('stripe_billing_version' => 2))
-    # rubocop:enable Rails/SkipsModelValidations
-  end
-
   trigger.after(:insert).for_each(:row) do
     "execute format('create sequence IF NOT EXISTS conv_dpid_seq_%s', NEW.id);"
   end
diff --git a/app/policies/account_policy.rb b/app/policies/account_policy.rb
index a5ebc54d9..17e4f7564 100644
--- a/app/policies/account_policy.rb
+++ b/app/policies/account_policy.rb
@@ -47,10 +47,6 @@ class AccountPolicy < ApplicationPolicy
     @account_user.administrator?
   end
 
-  def v2_buy?
-    @account_user.administrator?
-  end
-
   def v2_subscribe?
     @account_user.administrator?
   end
diff --git a/app/views/api/v1/models/_account.json.jbuilder b/app/views/api/v1/models/_account.json.jbuilder
index d4d1c45ee..af9235b4b 100644
--- a/app/views/api/v1/models/_account.json.jbuilder
+++ b/app/views/api/v1/models/_account.json.jbuilder
@@ -16,7 +16,6 @@ if resource.custom_attributes.present?
       json.marked_for_deletion_reason resource.custom_attributes['marked_for_deletion_reason']
     end
     # V2 Billing attributes
-    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?
     json.stripe_pricing_plan_id resource.custom_attributes['stripe_pricing_plan_id'] if resource.custom_attributes['stripe_pricing_plan_id'].present?
     json.stripe_cadence_id resource.custom_attributes['stripe_cadence_id'] if resource.custom_attributes['stripe_cadence_id'].present?
diff --git a/enterprise/app/controllers/enterprise/api/v1/accounts_controller.rb b/enterprise/app/controllers/enterprise/api/v1/accounts_controller.rb
index 66add3777..c372d857e 100644
--- a/enterprise/app/controllers/enterprise/api/v1/accounts_controller.rb
+++ b/enterprise/app/controllers/enterprise/api/v1/accounts_controller.rb
@@ -3,6 +3,7 @@ class Enterprise::Api::V1::AccountsController < Api::BaseController
   before_action :fetch_account
   before_action :check_authorization
   before_action :check_cloud_env, only: [:limits, :toggle_deletion]
+  before_action :validate_topup_amount, only: [:v2_topup]
 
   def subscription
     if stripe_customer_id.blank? && @account.custom_attributes['is_creating_customer'].blank?
@@ -72,7 +73,6 @@ class Enterprise::Api::V1::AccountsController < Api::BaseController
 
   def v2_pricing_plans
     plans = Enterprise::Billing::V2::PlanCatalog.plans
-
     render json: { pricing_plans: plans }
   end
 
@@ -82,11 +82,8 @@ class Enterprise::Api::V1::AccountsController < Api::BaseController
   end
 
   def v2_topup
-    amount = params[:credits].to_i
-    return render json: { error: 'Topup amount must be greater than 0' }, status: :unprocessable_entity if amount <= 0
-
     service = Enterprise::Billing::V2::TopupService.new(account: @account)
-    result = service.create_topup(credits: amount)
+    result = service.create_topup(credits: params[:credits].to_i)
 
     if result[:success]
       render json: { success: true, message: result[:message] }
@@ -114,12 +111,7 @@ class Enterprise::Api::V1::AccountsController < Api::BaseController
     result = service.cancel_subscription
 
     if result[:success]
-      render json: {
-        success: true,
-        message: result[:message],
-        cancel_at_period_end: result[:cancel_at_period_end],
-        period_end: result[:period_end]
-      }
+      render json: result
     else
       render json: { error: result[:message] }, status: :unprocessable_entity
     end
@@ -199,6 +191,13 @@ class Enterprise::Api::V1::AccountsController < Api::BaseController
     quantity.positive? ? quantity : 1
   end
 
+  def validate_topup_amount
+    amount = params[:credits].to_i
+    return if amount.positive?
+
+    render json: { error: 'Topup amount must be greater than 0' }, status: :unprocessable_entity
+  end
+
   def pundit_user
     {
       user: current_user,
diff --git a/enterprise/app/controllers/enterprise/webhooks/stripe_controller.rb b/enterprise/app/controllers/enterprise/webhooks/stripe_controller.rb
index 6aa882a0a..747f70d69 100644
--- a/enterprise/app/controllers/enterprise/webhooks/stripe_controller.rb
+++ b/enterprise/app/controllers/enterprise/webhooks/stripe_controller.rb
@@ -13,7 +13,7 @@ class Enterprise::Webhooks::StripeController < ActionController::API
 
       # Check if this is a V2 billing event
       if v2_billing_event?(event)
-        handle_v2_event(event)
+        ::Enterprise::Billing::V2::WebhookHandlerService.new.perform(event: event)
       else
         ::Enterprise::Billing::HandleStripeEventService.new.perform(event: event)
       end
@@ -35,62 +35,14 @@ class Enterprise::Webhooks::StripeController < ActionController::API
     parsed_payload = JSON.parse(payload)
     event_type = parsed_payload['type']
 
-    # Use V2 webhook secret for V2 events, V1 secret for everything else
-    if event_type&.start_with?('v2.')
+    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)
-    event.type.start_with?('v2.')
-  end
-
-  def handle_v2_event(event)
-    account = find_account_for_v2_event(event)
-    return unless account && account_v2_enabled?(account)
-
-    service = ::Enterprise::Billing::V2::WebhookHandlerService.new(account: account)
-    service.process(event)
-  end
-
-  def find_account_for_v2_event(event)
-    related_object = event.related_object
-    subscription_id = related_object.id
-
-    customer_id = fetch_customer_id_from_subscription(subscription_id)
-    if customer_id.present?
-      account = Account.find_by("custom_attributes->>'stripe_customer_id' = ?", customer_id)
-      return account if account
-    end
-
-    Rails.logger.warn "Could not find account for subscription #{subscription_id}"
-    nil
-  end
-
-  def fetch_customer_id_from_subscription(subscription_id)
-    # Step 1: Fetch subscription
-    subscription = StripeV2Client.request(
-      :get,
-      "/v2/billing/pricing_plan_subscriptions/#{subscription_id}",
-      {},
-      { api_key: ENV.fetch('STRIPE_SECRET_KEY', nil), stripe_version: '2025-08-27.preview' }
-    )
-    return nil unless subscription&.billing_cadence
-
-    # Step 2: Fetch billing cadence
-    cadence = StripeV2Client.request(
-      :get,
-      "/v2/billing/cadences/#{subscription.billing_cadence}",
-      {},
-      { api_key: ENV.fetch('STRIPE_SECRET_KEY', nil), stripe_version: '2025-08-27.preview' }
-    )
-    # Step 3: Extract customer from payer
-    cadence.payer&.customer
-  end
-
-  def account_v2_enabled?(_account)
-    ENV.fetch('STRIPE_BILLING_V2_ENABLED', 'false') == 'true'
+  def v2_billing_event?(event_type)
+    event_type.start_with?('v2.')
   end
 end
diff --git a/enterprise/app/jobs/captain/conversation/response_builder_job.rb b/enterprise/app/jobs/captain/conversation/response_builder_job.rb
index 15f2ace56..cd781041e 100644
--- a/enterprise/app/jobs/captain/conversation/response_builder_job.rb
+++ b/enterprise/app/jobs/captain/conversation/response_builder_job.rb
@@ -114,6 +114,7 @@ class Captain::Conversation::ResponseBuilderJob < ApplicationJob
 
   def handle_error(error)
     log_error(error)
+    refund_credit
     process_action('handoff')
     true
   end
@@ -125,4 +126,18 @@ class Captain::Conversation::ResponseBuilderJob < ApplicationJob
   def captain_v2_enabled?
     return account.feature_enabled?('captain_integration_v2')
   end
+
+  def refund_credit
+    credit_service = Enterprise::Ai::CaptainCreditService.new(conversation: @conversation)
+    credit_service.check_and_use_credits(
+      feature: 'ai_captain_conversation',
+      amount: -1, # Negative to refund
+      metadata: {
+        'assistant_id' => @assistant.id,
+        'conversation_id' => @conversation.id,
+        'inbox_id' => @inbox.id,
+        'refund' => true
+      }
+    )
+  end
 end
diff --git a/enterprise/app/jobs/enterprise/create_stripe_customer_job.rb b/enterprise/app/jobs/enterprise/create_stripe_customer_job.rb
index 6ccaa2f33..6b90cbec5 100644
--- a/enterprise/app/jobs/enterprise/create_stripe_customer_job.rb
+++ b/enterprise/app/jobs/enterprise/create_stripe_customer_job.rb
@@ -2,7 +2,6 @@ class Enterprise::CreateStripeCustomerJob < ApplicationJob
   queue_as :default
 
   def perform(account)
-    # Use V1 service - creates customer and stores customer_id
     Enterprise::Billing::CreateStripeCustomerService.new(account: account).perform
   end
 end
diff --git a/enterprise/app/services/captain/copilot/chat_service.rb b/enterprise/app/services/captain/copilot/chat_service.rb
index 00c6f6320..d439a6e49 100644
--- a/enterprise/app/services/captain/copilot/chat_service.rb
+++ b/enterprise/app/services/captain/copilot/chat_service.rb
@@ -25,7 +25,6 @@ class Captain::Copilot::ChatService < Llm::BaseOpenAiService
 
     unless credit_result[:success]
       error_message = credit_result[:message] || 'Insufficient credits'
-      Rails.logger.warn("#{self.class.name} Credit check failed for account #{@account.id}: #{error_message}")
       return { error: error_message, error_code: 402 }
     end
 
diff --git a/enterprise/app/services/enterprise/billing/concerns/plan_feature_manager.rb b/enterprise/app/services/enterprise/billing/concerns/plan_feature_manager.rb
index e487d5bcd..228209a1f 100644
--- a/enterprise/app/services/enterprise/billing/concerns/plan_feature_manager.rb
+++ b/enterprise/app/services/enterprise/billing/concerns/plan_feature_manager.rb
@@ -82,14 +82,10 @@ module Enterprise::Billing::Concerns::PlanFeatureManager
 
   def enable_account_manually_managed_features
     # Get manually managed features from internal attributes using the service
-    return unless defined?(Internal::Accounts::InternalAttributesService)
-
     service = Internal::Accounts::InternalAttributesService.new(account)
     features = service.manually_managed_features
 
     # Enable each feature
     account.enable_features(*features) if features.present?
-  rescue StandardError
-    # Silently handle errors - account will continue with plan-specific features
   end
 end
diff --git a/enterprise/app/services/enterprise/billing/create_session_service.rb b/enterprise/app/services/enterprise/billing/create_session_service.rb
index f231e01bd..ad4f8f45b 100644
--- a/enterprise/app/services/enterprise/billing/create_session_service.rb
+++ b/enterprise/app/services/enterprise/billing/create_session_service.rb
@@ -1,12 +1,9 @@
 class Enterprise::Billing::CreateSessionService
-  PORTAL_CONFIGURATION_ID = 'bpc_1SI88PF3O6TPVU2azyI0ek2W'.freeze
-
   def create_session(customer_id, return_url = ENV.fetch('FRONTEND_URL'))
     Stripe::BillingPortal::Session.create(
       {
         customer: customer_id,
-        return_url: return_url,
-        configuration: PORTAL_CONFIGURATION_ID
+        return_url: return_url
       }
     )
   end
diff --git a/enterprise/app/services/enterprise/billing/create_stripe_customer_service.rb b/enterprise/app/services/enterprise/billing/create_stripe_customer_service.rb
index 594032200..e4df1050b 100644
--- a/enterprise/app/services/enterprise/billing/create_stripe_customer_service.rb
+++ b/enterprise/app/services/enterprise/billing/create_stripe_customer_service.rb
@@ -1,33 +1,69 @@
 class Enterprise::Billing::CreateStripeCustomerService
   pattr_initialize [:account!]
 
-  def perform
-    return if customer_exists?
+  DEFAULT_QUANTITY = 2
 
-    customer_id = create_customer
-    save_customer_id(customer_id)
+  def perform
+    return if existing_subscription?
+
+    customer_id = prepare_customer_id
+    subscription = Stripe::Subscription.create(
+      {
+        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
 
-  def customer_exists?
-    account.custom_attributes['stripe_customer_id'].present?
+  def prepare_customer_id
+    customer_id = account.custom_attributes['stripe_customer_id']
+    if customer_id.blank?
+      customer = Stripe::Customer.create({ name: account.name, email: billing_email })
+      customer_id = customer.id
+    end
+    customer_id
   end
 
-  def create_customer
-    customer = Stripe::Customer.create({ name: account.name, email: billing_email })
-    customer.id
-  end
-
-  def save_customer_id(customer_id)
-    account.update!(
-      custom_attributes: {
-        stripe_customer_id: customer_id
-      }
-    )
+  def default_quantity
+    default_plan['default_quantity'] || DEFAULT_QUANTITY
   end
 
   def billing_email
     account.administrators.first.email
   end
+
+  def default_plan
+    installation_config = InstallationConfig.find_by(name: 'CHATWOOT_CLOUD_PLANS')
+    @default_plan ||= installation_config.value.first
+  end
+
+  def price_id
+    price_ids = default_plan['price_ids']
+    price_ids.first
+  end
+
+  def existing_subscription?
+    stripe_customer_id = account.custom_attributes['stripe_customer_id']
+    return false if stripe_customer_id.blank?
+
+    subscriptions = Stripe::Subscription.list(
+      {
+        customer: stripe_customer_id,
+        status: 'active',
+        limit: 1
+      }
+    )
+    subscriptions.data.present?
+  end
 end
diff --git a/enterprise/app/services/enterprise/billing/handle_stripe_event_service.rb b/enterprise/app/services/enterprise/billing/handle_stripe_event_service.rb
index e2ab8aff2..bb1df4f54 100644
--- a/enterprise/app/services/enterprise/billing/handle_stripe_event_service.rb
+++ b/enterprise/app/services/enterprise/billing/handle_stripe_event_service.rb
@@ -15,6 +15,8 @@ class Enterprise::Billing::HandleStripeEventService
       process_credit_grant_created
     when 'billing.credit_grant.updated'
       process_credit_grant_updated
+    else
+      Rails.logger.debug { "Unhandled event type: #{event.type}" }
     end
   end
 
diff --git a/enterprise/app/services/enterprise/billing/v2/checkout_session_service.rb b/enterprise/app/services/enterprise/billing/v2/checkout_session_service.rb
index 3271a76df..739285721 100644
--- a/enterprise/app/services/enterprise/billing/v2/checkout_session_service.rb
+++ b/enterprise/app/services/enterprise/billing/v2/checkout_session_service.rb
@@ -28,15 +28,11 @@ class Enterprise::Billing::V2::CheckoutSessionService < Enterprise::Billing::V2:
     create_checkout_session
   rescue Stripe::StripeError => e
     { success: false, message: "Stripe API error: #{e.message}", error: e }
-  rescue StandardError => e
-    { success: false, message: "Checkout error: #{e.message}", error: e }
   end
 
   private
 
   def validate_params
-    raise StandardError, 'Pricing Plan ID required' if @pricing_plan_id.blank?
-
     customer_id = custom_attribute('stripe_customer_id')
     raise StandardError, 'Customer ID required. Please create a Stripe customer first.' if customer_id.blank?
   end
diff --git a/enterprise/app/services/enterprise/billing/v2/concerns/payment_intent_handler.rb b/enterprise/app/services/enterprise/billing/v2/concerns/payment_intent_handler.rb
deleted file mode 100644
index 8fb6a137b..000000000
--- a/enterprise/app/services/enterprise/billing/v2/concerns/payment_intent_handler.rb
+++ /dev/null
@@ -1,66 +0,0 @@
-module Enterprise::Billing::V2::Concerns::PaymentIntentHandler
-  extend ActiveSupport::Concern
-
-  private
-
-  def create_payment_if_needed(intent, intent_id)
-    amount_due = intent.amount_details&.total || intent.amount_details.total
-    return nil unless amount_due&.to_i&.positive?
-
-    payment_method_id = fetch_default_payment_method
-    create_upfront_payment_intent(amount_due, intent.currency, payment_method_id, intent_id)
-  end
-
-  def fetch_default_payment_method
-    customer = Stripe::Customer.retrieve(
-      @customer_id,
-      { api_key: ENV.fetch('STRIPE_SECRET_KEY', nil), stripe_version: '2025-08-27.preview' }
-    )
-    customer.invoice_settings&.default_payment_method
-  end
-
-  def create_upfront_payment_intent(amount_due, currency, payment_method_id, intent_id)
-    payment_intent = Stripe::PaymentIntent.create(
-      payment_intent_params(amount_due, currency, payment_method_id, intent_id),
-      { api_key: ENV.fetch('STRIPE_SECRET_KEY', nil), stripe_version: '2025-08-27.preview' }
-    )
-
-    payment_intent.id
-  end
-
-  def payment_intent_params(amount_due, currency, payment_method_id, intent_id)
-    {
-      amount: amount_due,
-      currency: currency || 'usd',
-      customer: @customer_id,
-      payment_method: payment_method_id,
-      automatic_payment_methods: {
-        enabled: true,
-        allow_redirects: 'never'
-      },
-      confirm: true,
-      off_session: true,
-      metadata: { billing_intent_id: intent_id }
-    }
-  end
-
-  def fetch_billing_intent(intent_id)
-    StripeV2Client.request(
-      :get,
-      "/v2/billing/intents/#{intent_id}",
-      {},
-      stripe_api_options
-    )
-  end
-
-  def commit_billing_intent(intent_id, payment_intent_id)
-    commit_params = payment_intent_id ? { payment_intent: payment_intent_id } : {}
-
-    StripeV2Client.request(
-      :post,
-      "/v2/billing/intents/#{intent_id}/commit",
-      commit_params,
-      stripe_api_options
-    )
-  end
-end
diff --git a/enterprise/app/services/enterprise/billing/v2/subscription_provisioning_service.rb b/enterprise/app/services/enterprise/billing/v2/subscription_provisioning_service.rb
index 79b3152ef..6bd595e40 100644
--- a/enterprise/app/services/enterprise/billing/v2/subscription_provisioning_service.rb
+++ b/enterprise/app/services/enterprise/billing/v2/subscription_provisioning_service.rb
@@ -1,21 +1,5 @@
 class Enterprise::Billing::V2::SubscriptionProvisioningService < Enterprise::Billing::V2::BaseService
-  # Features for each plan tier (matching the plan hierarchy)
-  STARTUP_FEATURES = %w[
-    inbound_emails
-    help_center
-    campaigns
-    team_management
-    channel_twitter
-    channel_facebook
-    channel_email
-    channel_instagram
-    captain_integration
-    advanced_search_indexing
-  ].freeze
-
-  BUSINESS_FEATURES = (STARTUP_FEATURES + %w[sla custom_roles]).freeze
-
-  ENTERPRISE_FEATURES = (BUSINESS_FEATURES + %w[audit_logs disable_branding saml]).freeze
+  include Enterprise::Billing::Concerns::PlanFeatureManager
 
   def provision(subscription_id:)
     # Retrieve pricing plan subscription details from Stripe V2 API
@@ -102,8 +86,15 @@ class Enterprise::Billing::V2::SubscriptionProvisioningService < Enterprise::Bil
     # Sync monthly credits based on plan
     sync_plan_credits(pricing_plan_id)
 
-    # Enable plan features based on plan
-    enable_plan_features(pricing_plan_id)
+    # Extract plan name and enable features using PlanFeatureManager
+    plan_definition = Enterprise::Billing::V2::PlanCatalog.definition_for(pricing_plan_id)
+    if plan_definition
+      plan_name = extract_plan_name(plan_definition)
+      enable_plan_specific_features(plan_name) if plan_name.present?
+    end
+
+    # Reset captain usage after provisioning
+    reset_captain_usage
   end
 
   def sync_plan_credits(pricing_plan_id)
@@ -115,35 +106,10 @@ class Enterprise::Billing::V2::SubscriptionProvisioningService < Enterprise::Bil
       .sync_monthly_credits(plan_credits.to_i)
   end
 
-  def enable_plan_features(pricing_plan_id)
-    plan_definition = Enterprise::Billing::V2::PlanCatalog.definition_for(pricing_plan_id)
-    return unless plan_definition
-
-    plan_tier = extract_plan_tier(plan_definition)
-    return unless plan_tier
-
-    features_to_enable = features_for_plan_tier(plan_tier)
-    return if features_to_enable.empty?
-
-    # Enable each feature using the account method
-    account.enable_features(*features_to_enable)
-  end
-
-  def extract_plan_tier(plan_definition)
-    plan_definition[:display_name].split.find { |word| %w[Startup Business Enterprise].include?(word) }
-  end
-
-  def features_for_plan_tier(plan_tier)
-    case plan_tier
-    when 'Startup'
-      STARTUP_FEATURES
-    when 'Business'
-      BUSINESS_FEATURES
-    when 'Enterprise'
-      ENTERPRISE_FEATURES
-    else
-      []
-    end
+  def extract_plan_name(plan_definition)
+    # Extract plan name like "Startup", "Business", or "Enterprise" from display_name
+    # e.g., "Chatwoot Startup" -> "Startup"
+    plan_definition[:display_name].split.find { |word| %w[Startup Startups Business Enterprise].include?(word) }
   end
 
   def stripe_api_options
diff --git a/enterprise/app/services/enterprise/billing/v2/subscription_service.rb b/enterprise/app/services/enterprise/billing/v2/subscription_service.rb
deleted file mode 100644
index 6118296df..000000000
--- a/enterprise/app/services/enterprise/billing/v2/subscription_service.rb
+++ /dev/null
@@ -1,44 +0,0 @@
-class Enterprise::Billing::V2::SubscriptionService < Enterprise::Billing::V2::BaseService
-  def migrate_to_v2(plan_type: 'startup', monthly_credits: 100)
-    return { success: false, message: 'Already on V2' } if v2_enabled?
-
-    with_locked_account do
-      apply_migration_attributes(plan_type, monthly_credits)
-      log_migration_grant(plan_type, monthly_credits)
-    end
-
-    { success: true, message: 'Successfully migrated to V2 billing' }
-  rescue StandardError => e
-    { success: false, message: e.message }
-  end
-
-  def update_plan(plan_type)
-    return { success: false, message: 'Not on V2 billing' } unless v2_enabled?
-
-    update_custom_attributes('plan_name' => plan_type.capitalize)
-
-    { success: true, plan: plan_type }
-  end
-
-  private
-
-  def apply_migration_attributes(plan_type, credits)
-    update_custom_attributes(
-      'stripe_billing_version' => 2,
-      'monthly_credits' => credits,
-      'topup_credits' => 0,
-      'plan_name' => plan_type.capitalize,
-      'subscription_status' => 'active'
-    )
-  end
-
-  def log_migration_grant(plan_type, credits)
-    log_credit_transaction(
-      type: 'grant',
-      amount: credits,
-      credit_type: 'monthly',
-      description: "Initial V2 migration grant - #{plan_type} plan",
-      metadata: { 'source' => 'migration', 'plan_type' => plan_type }
-    )
-  end
-end
diff --git a/enterprise/app/services/enterprise/billing/v2/topup_service.rb b/enterprise/app/services/enterprise/billing/v2/topup_service.rb
index 547cdab2f..0b2249a99 100644
--- a/enterprise/app/services/enterprise/billing/v2/topup_service.rb
+++ b/enterprise/app/services/enterprise/billing/v2/topup_service.rb
@@ -12,8 +12,6 @@ class Enterprise::Billing::V2::TopupService < Enterprise::Billing::V2::BaseServi
     end
   rescue Stripe::StripeError => e
     { success: false, message: "Stripe error: #{e.message}" }
-  rescue StandardError => e
-    { success: false, message: "Topup error: #{e.message}" }
   end
 
   private
diff --git a/enterprise/app/services/enterprise/billing/v2/webhook_handler_service.rb b/enterprise/app/services/enterprise/billing/v2/webhook_handler_service.rb
index 39e191347..8f1f0c4b8 100644
--- a/enterprise/app/services/enterprise/billing/v2/webhook_handler_service.rb
+++ b/enterprise/app/services/enterprise/billing/v2/webhook_handler_service.rb
@@ -1,22 +1,62 @@
-class Enterprise::Billing::V2::WebhookHandlerService < Enterprise::Billing::V2::BaseService
-  def process(event)
-    case event.type
+class Enterprise::Billing::V2::WebhookHandlerService
+  def perform(event:)
+    return { success: false, message: 'Account not found' } if account.blank?
+
+    @event = event
+
+    case @event.type
     when 'v2.billing.pricing_plan_subscription.servicing_activated'
-      Rails.logger.info "Handling subscription servicing activated event: #{event.related_object.id}"
-      Rails.logger.info "Related object: #{event.related_object.inspect}"
-      handle_subscription_servicing_activated(event.related_object.id)
+      Rails.logger.info "Handling subscription servicing activated event: #{@event.related_object.id}"
+      handle_subscription_servicing_activated(@event.related_object.id)
     else
       { success: true }
     end
   rescue StandardError => e
+    Rails.logger.error "Error processing V2 webhook: #{e.message}"
     { success: false, error: e.message }
   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 = StripeV2Client.request(
+      :get,
+      "/v2/billing/pricing_plan_subscriptions/#{subscription_id}",
+      {},
+      stripe_api_options
+    )
+    return nil unless subscription&.billing_cadence
+
+    cadence = StripeV2Client.request(
+      :get,
+      "/v2/billing/cadences/#{subscription.billing_cadence}",
+      {},
+      stripe_api_options
+    )
+    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 stripe_api_options
+    { api_key: ENV.fetch('STRIPE_SECRET_KEY', nil), stripe_version: '2025-08-27.preview' }
+  end
 end
diff --git a/enterprise/app/services/messages/audio_transcription_service.rb b/enterprise/app/services/messages/audio_transcription_service.rb
index 278f41d71..725d5ef0e 100644
--- a/enterprise/app/services/messages/audio_transcription_service.rb
+++ b/enterprise/app/services/messages/audio_transcription_service.rb
@@ -15,6 +15,10 @@ class Messages::AudioTranscriptionService < Llm::BaseOpenAiService
     transcriptions = transcribe_audio
     Rails.logger.info "Audio transcription successful: #{transcriptions}"
     { success: true, transcriptions: transcriptions }
+  rescue StandardError => e
+    # Refund credit if transcription failed
+    refund_credit
+    raise e
   end
 
   private
@@ -26,6 +30,20 @@ class Messages::AudioTranscriptionService < Llm::BaseOpenAiService
     account.usage_limits[:captain][:responses][:current_available].positive?
   end
 
+  def refund_credit
+    credit_service = Enterprise::Ai::CaptainCreditService.new(account: account)
+    credit_service.check_and_use_credits(
+      feature: 'ai_audio_transcription',
+      amount: -1, # Negative to refund
+      metadata: {
+        'message_id' => message.id,
+        'attachment_id' => attachment.id,
+        'conversation_id' => message.conversation_id,
+        'refund' => true
+      }
+    )
+  end
+
   def fetch_audio_file
     temp_dir = Rails.root.join('tmp/uploads')
     FileUtils.mkdir_p(temp_dir)
diff --git a/spec/enterprise/controllers/enterprise/webooks/stripe_controller_spec.rb b/spec/enterprise/controllers/enterprise/webooks/stripe_controller_spec.rb
index c8e4b3f00..3b5b68e46 100644
--- a/spec/enterprise/controllers/enterprise/webooks/stripe_controller_spec.rb
+++ b/spec/enterprise/controllers/enterprise/webooks/stripe_controller_spec.rb
@@ -19,24 +19,16 @@ RSpec.describe 'Enterprise::Webhooks::StripeController', type: :request do
     end
 
     it 'delegates v2 billing events to the v2 webhook handler' do
-      account = create(:account)
-      account.update!(custom_attributes: (account.custom_attributes || {}).merge(
-        'stripe_billing_version' => 2,
-        'stripe_customer_id' => 'cus_123'
-      ))
-
-      event_object = double('StripeObject', customer: 'cus_123')
-      event = double('Stripe::Event', type: 'billing.credit_grant.created', data: double(object: event_object))
-      handler_double = instance_double(Enterprise::Billing::V2::WebhookHandlerService, process: { success: true })
+      event = double('Stripe::Event', type: 'v2.billing.pricing_plan_subscription.servicing_activated')
+      handler_double = instance_double(Enterprise::Billing::V2::WebhookHandlerService, perform: { success: true })
 
       allow(Stripe::Webhook).to receive(:construct_event).and_return(event)
-      allow(Enterprise::Billing::HandleStripeEventService).to receive(:new)
-      allow(Enterprise::Billing::V2::WebhookHandlerService).to receive(:new).with(account: account).and_return(handler_double)
+      allow(Enterprise::Billing::V2::WebhookHandlerService).to receive(:new).and_return(handler_double)
 
       post '/enterprise/webhooks/stripe', headers: { 'Stripe-Signature': 'test' }, params: params
 
-      expect(Enterprise::Billing::V2::WebhookHandlerService).to have_received(:new).with(account: account)
-      expect(handler_double).to have_received(:process).with(event)
+      expect(Enterprise::Billing::V2::WebhookHandlerService).to have_received(:new)
+      expect(handler_double).to have_received(:perform).with(event: event)
       expect(response).to have_http_status(:ok)
     end
 
diff --git a/spec/enterprise/services/enterprise/billing/v2/subscription_service_spec.rb b/spec/enterprise/services/enterprise/billing/v2/subscription_service_spec.rb
deleted file mode 100644
index b9bb36a27..000000000
--- a/spec/enterprise/services/enterprise/billing/v2/subscription_service_spec.rb
+++ /dev/null
@@ -1,61 +0,0 @@
-require 'rails_helper'
-
-describe Enterprise::Billing::V2::SubscriptionService do
-  let(:account) { create(:account) }
-  let(:service) { described_class.new(account: account) }
-
-  describe '#migrate_to_v2' do
-    it 'updates account attributes and logs initial credit grant' do # rubocop:disable RSpec/MultipleExpectations
-      result = nil
-
-      expect do
-        result = service.migrate_to_v2(plan_type: 'startup', monthly_credits: 800)
-      end.to change { account.reload.credit_transactions.count }.by(1)
-
-      account.reload
-      expect(result).to include(success: true)
-      expect(account.custom_attributes['stripe_billing_version']).to eq(2)
-      expect(account.custom_attributes['monthly_credits']).to eq(800)
-      expect(account.custom_attributes['plan_name']).to eq('Startup')
-
-      transaction = account.credit_transactions.order(created_at: :desc).first
-      expect(transaction.amount).to eq(800)
-      expect(transaction.metadata['source']).to eq('migration')
-      expect(transaction.metadata['plan_type']).to eq('startup')
-    end
-
-    it 'uses default credits when not specified' do
-      result = service.migrate_to_v2
-
-      expect(result).to include(success: true)
-      expect(account.reload.custom_attributes['monthly_credits']).to eq(100)
-    end
-
-    it 'returns error when already on v2' do
-      account.update!(custom_attributes: (account.custom_attributes || {}).merge('stripe_billing_version' => 2))
-
-      result = service.migrate_to_v2(monthly_credits: 500)
-
-      expect(result[:success]).to be(false)
-      expect(result[:message]).to eq('Already on V2')
-    end
-  end
-
-  describe '#update_plan' do
-    it 'updates plan name when on v2 billing' do
-      account.update!(custom_attributes: (account.custom_attributes || {}).merge('stripe_billing_version' => 2))
-
-      result = service.update_plan('business')
-
-      expect(result).to include(success: true, plan: 'business')
-      expect(account.reload.custom_attributes['plan_name']).to eq('Business')
-    end
-
-    it 'returns error when account not migrated' do
-      result = service.update_plan('business')
-
-      expect(result[:success]).to be(false)
-      expect(result[:message]).to eq('Not on V2 billing')
-    end
-  end
-end
diff --git a/spec/enterprise/services/enterprise/billing/v2/webhook_handler_service_spec.rb b/spec/enterprise/services/enterprise/billing/v2/webhook_handler_service_spec.rb
index 589fe1e80..34ce4e194 100644
--- a/spec/enterprise/services/enterprise/billing/v2/webhook_handler_service_spec.rb
+++ b/spec/enterprise/services/enterprise/billing/v2/webhook_handler_service_spec.rb
@@ -2,25 +2,44 @@ require 'rails_helper'
 # rubocop:disable RSpec/VerifiedDoubles
 
 describe Enterprise::Billing::V2::WebhookHandlerService do
-  let(:account) { create(:account) }
-  let(:service) { described_class.new(account: account) }
+  let(:account) do
+    create(:account, custom_attributes: { 'stripe_customer_id' => 'cus_123', 'stripe_billing_version' => 2, 'pending_subscription_quantity' => 5 })
+  end
+  let(:service) { described_class.new }
   let(:credit_service) { instance_double(Enterprise::Billing::V2::CreditManagementService) }
 
   before do
-    account.update!(custom_attributes: { 'stripe_billing_version' => 2, 'pending_subscription_quantity' => 5 })
     allow(Enterprise::Billing::V2::CreditManagementService).to receive(:new).with(account: account).and_return(credit_service)
+    allow(ENV).to receive(:fetch).and_call_original
   end
 
-  describe '#process' do
+  describe '#perform' do
     context 'when handling subscription servicing activated' do
       let(:subscription_response) do
         OpenStruct.new(
           id: 'bpps_subscription_123',
           pricing_plan: 'bpp_business_plan_123',
+          billing_cadence: 'cadence_123',
           component_values: [{ 'type' => 'license_fee', 'quantity' => 5 }]
         )
       end
 
+      let(:cadence_response) do
+        OpenStruct.new(
+          id: 'cadence_123',
+          payer: OpenStruct.new(customer: 'cus_123')
+        )
+      end
+
+      let(:provisioning_response) do
+        {
+          success: true,
+          subscription_id: 'bpps_subscription_123',
+          pricing_plan_id: 'bpp_business_plan_123',
+          quantity: 5
+        }
+      end
+
       let(:event) do
         double(
           'Stripe::Event',
@@ -36,49 +55,47 @@ describe Enterprise::Billing::V2::WebhookHandlerService do
 
       before do
         create(:installation_config, name: 'STRIPE_BUSINESS_PLAN_ID', value: 'bpp_business_plan_123')
-        allow(StripeV2Client).to receive(:request).and_return(subscription_response)
+
+        # Mock account lookup via subscription and cadence
+        allow(StripeV2Client).to receive(:request)
+          .with(:get, '/v2/billing/pricing_plan_subscriptions/bpps_subscription_123', anything, anything)
+          .and_return(subscription_response)
+        allow(StripeV2Client).to receive(:request)
+          .with(:get, '/v2/billing/cadences/cadence_123', anything, anything)
+          .and_return(cadence_response)
+
+        # Mock provisioning service
+        provisioning_service = instance_double(Enterprise::Billing::V2::SubscriptionProvisioningService)
+        allow(Enterprise::Billing::V2::SubscriptionProvisioningService).to receive(:new).with(account: account).and_return(provisioning_service)
+        allow(provisioning_service).to receive(:provision).and_return(provisioning_response)
+
         allow(credit_service).to receive(:sync_monthly_credits)
       end
 
-      it 'returns success with subscription details' do
-        result = service.process(event)
+      it 'delegates to subscription provisioning service' do
+        result = service.perform(event: event)
 
         expect(result[:success]).to be(true), "Expected success but got: #{result.inspect}"
-        expect(result[:subscription_id]).to eq('bpps_subscription_123')
-        expect(result[:pricing_plan_id]).to eq('bpp_business_plan_123')
-        expect(result[:quantity]).to eq(5)
-      end
-
-      it 'updates account custom attributes' do
-        service.process(event)
-
-        expect(account.custom_attributes['stripe_subscription_id']).to eq('bpps_subscription_123')
-        expect(account.custom_attributes['stripe_pricing_plan_id']).to eq('bpp_business_plan_123')
-        expect(account.custom_attributes['subscribed_quantity']).to eq(5)
-        expect(account.custom_attributes['subscription_status']).to eq('active')
-        expect(account.custom_attributes['plan_name']).to eq('Chatwoot Business')
-      end
-
-      it 'syncs monthly credits' do
-        service.process(event)
-
-        expect(credit_service).to have_received(:sync_monthly_credits).with(50_000)
-      end
-
-      it 'provisions features for the plan' do
-        service.process(event)
-
-        enabled_feature_names = account.enabled_features.map(&:first)
-        expect(enabled_feature_names).to match_array(expected_features)
+        expect(Enterprise::Billing::V2::SubscriptionProvisioningService).to have_received(:new).with(account: account)
       end
     end
 
     context 'when handling unknown event' do
       it 'returns success' do
-        related_object = OpenStruct.new(id: 'unknown_id')
+        related_object = OpenStruct.new(id: 'bpps_subscription_123')
         event = double('Stripe::Event', type: 'unknown.event', related_object: related_object)
 
-        result = service.process(event)
+        # Mock account lookup
+        subscription_response = OpenStruct.new(billing_cadence: 'cadence_123')
+        cadence_response = OpenStruct.new(payer: OpenStruct.new(customer: 'cus_123'))
+        allow(StripeV2Client).to receive(:request)
+          .with(:get, '/v2/billing/pricing_plan_subscriptions/bpps_subscription_123', anything, anything)
+          .and_return(subscription_response)
+        allow(StripeV2Client).to receive(:request)
+          .with(:get, '/v2/billing/cadences/cadence_123', anything, anything)
+          .and_return(cadence_response)
+
+        result = service.perform(event: event)
 
         expect(result[:success]).to be(true)
       end