raven.rb

# how can I change this middleware to only call Raven.captureException when a message is placed in the retries queue, let's say, for the third time?

module Raven
  class Sidekiq
    def call(worker, msg, queue)
      begin
        yield
      rescue => ex
        Raven.captureException(ex)
        raise
      end
    end
  end
end

::Sidekiq.configure_server do |config|
  config.server_middleware do |chain|
    chain.add ::Raven::Sidekiq
  end
end

That issue is covered in the FAQ, use an after_commit callback.