module MailerMonitoringConcern extend ActiveSupport::Concern included do # Intercept & log any error, then re-raise so job will retry. # NOTE: rescue_from order matters, later matchers are tried first. rescue_from StandardError, with: :log_and_raise_delivery_error # Don’t retry to send a message if the server rejects the recipient address rescue_from Net::SMTPSyntaxError do |_exception| message.perform_deliveries = false end rescue_from Net::SMTPServerBusy do |exception| if /unexpected recipients/.match?(exception.message) message.perform_deliveries = false else log_and_raise_delivery_error(exception) end end def log_and_raise_delivery_error(exception) EmailEvent.create_from_message!(message, status: "dispatch_error") Sentry.capture_exception(exception, extra: { to: message.to, subject: message.subject }) # re-raise another error so job will retry later raise MailDeliveryError.new(exception) end end end