diff --git a/db/migrate/20260709000000_enable_api_and_webhooks_for_existing_accounts.rb b/db/migrate/20260709000000_enable_api_and_webhooks_for_existing_accounts.rb
new file mode 100644
index 000000000..8c503ad95
--- /dev/null
+++ b/db/migrate/20260709000000_enable_api_and_webhooks_for_existing_accounts.rb
@@ -0,0 +1,12 @@
+# Enable api_and_webhooks for existing accounts.
+# Like 20260120121402_enable_captain_tasks_for_existing_accounts.rb, we don't need
+# to update ACCOUNT_LEVEL_FEATURE_DEFAULTS or clear GlobalConfig cache because
+# api_and_webhooks has `enabled: true` in features.yml - ConfigLoader handles the
+# defaults on deploy automatically.
+class EnableApiAndWebhooksForExistingAccounts < ActiveRecord::Migration[7.0]
+  def up
+    Account.find_in_batches(batch_size: 100) do |accounts|
+      accounts.each { |account| account.enable_features!('api_and_webhooks') }
+    end
+  end
+end
diff --git a/db/schema.rb b/db/schema.rb
index 5e506a475..aceb7b419 100644
--- a/db/schema.rb
+++ b/db/schema.rb
@@ -10,7 +10,7 @@
 #
 # It's strongly recommended that you check this file into your version control system.
 
-ActiveRecord::Schema[7.1].define(version: 2026_07_06_215758) do
+ActiveRecord::Schema[7.1].define(version: 2026_07_09_000000) do
   # These extensions should be enabled to support this database
   enable_extension "pg_stat_statements"
   enable_extension "pg_trgm"
diff --git a/lib/tasks/api_and_webhooks_migration.rake b/lib/tasks/api_and_webhooks_migration.rake
new file mode 100644
index 000000000..a92aaa81e
--- /dev/null
+++ b/lib/tasks/api_and_webhooks_migration.rake
@@ -0,0 +1,59 @@
+# Grandfather api_and_webhooks for existing accounts (cloud only).
+#
+# Adds api_and_webhooks to each account's manually_managed_features internal
+# attribute so per-account billing reconciles never strip the feature from
+# accounts that existed before the flag was introduced. Idempotent.
+#
+# Usage Examples:
+#   # Grandfather a single account
+#   ACCOUNT_ID=1 bundle exec rake api_and_webhooks:grandfather
+#
+#   # Grandfather all accounts in the installation
+#   bundle exec rake api_and_webhooks:grandfather
+# rubocop:disable Metrics/BlockLength
+namespace :api_and_webhooks do
+  desc 'Grandfather api_and_webhooks via manually_managed_features for existing accounts'
+  task grandfather: :environment do
+    abort 'Aborted. This task requires the enterprise edition.' unless ChatwootApp.enterprise?
+
+    account_id = ENV.fetch('ACCOUNT_ID', nil)
+    accounts = account_id.present? ? Account.where(id: account_id) : Account.all
+
+    if account_id.blank?
+      print 'No ACCOUNT_ID specified. This will grandfather ALL accounts. Continue? [y/N] '
+      abort 'Aborted.' unless $stdin.gets.chomp.casecmp('y').zero?
+    end
+
+    if account_id.present? && accounts.empty?
+      puts "Error: Account with ID #{account_id} not found"
+      exit(1)
+    end
+
+    total = accounts.count
+    puts "Grandfathering api_and_webhooks for #{total} account(s)..."
+
+    updated = 0
+    skipped = 0
+    errored = 0
+
+    accounts.find_each do |account|
+      service = Internal::Accounts::InternalAttributesService.new(account)
+      features = service.manually_managed_features
+
+      if features.include?('api_and_webhooks')
+        skipped += 1
+        next
+      end
+
+      service.manually_managed_features = features + ['api_and_webhooks']
+      account.enable_features!('api_and_webhooks')
+      updated += 1
+    rescue StandardError => e
+      errored += 1
+      puts "  Account #{account.id} — error: #{e.message}"
+    end
+
+    puts "Done! Updated: #{updated}, Skipped: #{skipped}, Errored: #{errored}, Total: #{total}"
+  end
+end
+# rubocop:enable Metrics/BlockLength