diff --git a/service/src/main/java/org/whispersystems/textsecuregcm/push/MessageSender.java b/service/src/main/java/org/whispersystems/textsecuregcm/push/MessageSender.java
index 9a3a7332b..c69a7670a 100644
--- a/service/src/main/java/org/whispersystems/textsecuregcm/push/MessageSender.java
+++ b/service/src/main/java/org/whispersystems/textsecuregcm/push/MessageSender.java
@@ -54,6 +54,7 @@ public class MessageSender {
 
   // Note that these names deliberately reference `MessageController` for metric continuity
   private static final String REJECT_OVERSIZE_MESSAGE_COUNTER_NAME = name(MessageSender.class, "rejectOversizeMessage");
+  private static final String OVERSIZE_MESSAGE_WARNING_COUNTER_NAME = name(MessageSender.class, "oversizeMessageWarning");
   private static final String CONTENT_SIZE_DISTRIBUTION_NAME = MetricsUtil.name(MessageSender.class, "messageContentSize");
   private static final String EMPTY_MESSAGE_LIST_COUNTER_NAME = MetricsUtil.name(MessageSender.class, "emptyMessageList");
 
@@ -69,6 +70,8 @@ public class MessageSender {
   @VisibleForTesting
   public static final int MAX_MESSAGE_SIZE = (int) DataSize.kibibytes(256).toBytes();
 
+  private static final int OVERSIZE_MESSAGE_WARNING_THRESHOLD = (int) DataSize.kibibytes(96).toBytes();
+
   @VisibleForTesting
   static final byte NO_EXCLUDED_DEVICE_ID = -1;
 
@@ -324,6 +327,14 @@ public class MessageSender {
         .register(Metrics.globalRegistry)
         .record(contentLength);
 
+    if (contentLength > OVERSIZE_MESSAGE_WARNING_THRESHOLD) {
+      Metrics.counter(OVERSIZE_MESSAGE_WARNING_COUNTER_NAME, Tags.of(platformTag,
+              Tag.of("multiRecipientMessage", String.valueOf(isMultiRecipientMessage)),
+              Tag.of("syncMessage", String.valueOf(isSyncMessage)),
+              Tag.of("story", String.valueOf(isStory))))
+          .increment();
+    }
+
     if (oversize) {
       Metrics.counter(REJECT_OVERSIZE_MESSAGE_COUNTER_NAME, Tags.of(platformTag,
               Tag.of("multiRecipientMessage", String.valueOf(isMultiRecipientMessage)),