diff --git a/lib/logstash/outputs/datadog_logs.rb b/lib/logstash/outputs/datadog_logs.rb
index 1387ad4..b7681c1 100644
--- a/lib/logstash/outputs/datadog_logs.rb
+++ b/lib/logstash/outputs/datadog_logs.rb
@@ -168,6 +168,7 @@ def send_retries(payload, max_retries, max_backoff)
           retries += 1
           retry
         end
+        @logger.error("Max number of retries reached, dropping message. Last exception: #{ex.message}")
       rescue => ex
         @logger.error("Unmanaged exception while sending log to datadog #{ex.message}")
       end