diff --git a/src/main/java/org/datadog/jenkins/plugins/datadog/clients/DatadogAgentClient.java b/src/main/java/org/datadog/jenkins/plugins/datadog/clients/DatadogAgentClient.java
index 9c591cb5..cf0562ae 100644
--- a/src/main/java/org/datadog/jenkins/plugins/datadog/clients/DatadogAgentClient.java
+++ b/src/main/java/org/datadog/jenkins/plugins/datadog/clients/DatadogAgentClient.java
@@ -66,6 +66,8 @@ of this software and associated documentation files (the "Software"), to deal
  */
 public class DatadogAgentClient implements DatadogClient {
 
+    private static final int PAYLOAD_SIZE_LIMIT = 5 * 1024 * 1024; // 5 MB
+
     private static volatile DatadogAgentClient instance = null;
     // Used to determine if the instance failed last validation last time, so
     // we do not keep retrying to create the instance and logging the same error
@@ -556,6 +558,10 @@ private void sendSpansToWebhook(Collection<Payload> spans) {
             }
 
             byte[] body = span.getJson().toString().getBytes(StandardCharsets.UTF_8);
+            if (body.length > PAYLOAD_SIZE_LIMIT) {
+                logger.severe("Dropping span because payload size (" + body.length + ") exceeds the allowed limit of " + PAYLOAD_SIZE_LIMIT);
+                continue;
+            }
 
             // webhook intake does not support batch requests
             logger.fine("Sending webhook");
diff --git a/src/main/java/org/datadog/jenkins/plugins/datadog/clients/DatadogApiClient.java b/src/main/java/org/datadog/jenkins/plugins/datadog/clients/DatadogApiClient.java
index 2573dbe1..288137cf 100644
--- a/src/main/java/org/datadog/jenkins/plugins/datadog/clients/DatadogApiClient.java
+++ b/src/main/java/org/datadog/jenkins/plugins/datadog/clients/DatadogApiClient.java
@@ -59,6 +59,8 @@ of this software and associated documentation files (the "Software"), to deal
  */
 public class DatadogApiClient implements DatadogClient {
 
+    private static final int PAYLOAD_SIZE_LIMIT = 5 * 1024 * 1024; // 5 MB
+
     private static volatile DatadogApiClient instance = null;
     // Used to determine if the instance failed last validation last time, so
     // we do not keep retrying to create the instance and logging the same error
@@ -515,6 +517,10 @@ private void sendSpans(Collection<Payload> spans) {
             }
 
             byte[] body = span.getJson().toString().getBytes(StandardCharsets.UTF_8);
+            if (body.length > PAYLOAD_SIZE_LIMIT) {
+                logger.severe("Dropping span because payload size (" + body.length + ") exceeds the allowed limit of " + PAYLOAD_SIZE_LIMIT);
+                continue;
+            }
 
             // webhook intake does not support batch requests
             logger.fine("Sending webhook");