diff --git a/sdk/cosmos/azure-cosmos/src/main/java/com/azure/cosmos/BridgeInternal.java b/sdk/cosmos/azure-cosmos/src/main/java/com/azure/cosmos/BridgeInternal.java
index 393988646eff4..a81b03f32de84 100644
--- a/sdk/cosmos/azure-cosmos/src/main/java/com/azure/cosmos/BridgeInternal.java
+++ b/sdk/cosmos/azure-cosmos/src/main/java/com/azure/cosmos/BridgeInternal.java
@@ -133,6 +133,17 @@ public static void setQueryPlanDiagnosticsContext(CosmosDiagnostics cosmosDiagno
         cosmosDiagnostics.getFeedResponseDiagnostics().setDiagnosticsContext(diagnosticsContext);
     }
 
+    @Warning(value = INTERNAL_USE_ONLY_WARNING)
+    public static <E extends CosmosException> E setRequestTimeline(E e, RequestTimeline requestTimeline) {
+        e.setRequestTimeline(requestTimeline);
+        return e;
+    }
+
+    @Warning(value = INTERNAL_USE_ONLY_WARNING)
+    public static <E extends CosmosException> RequestTimeline getRequestTimeline(E e) {
+        return e.getRequestTimeline();
+    }
+
     @Warning(value = INTERNAL_USE_ONLY_WARNING)
     public static <E extends CosmosException> E setResourceAddress(E e, String resourceAddress) {
         e.setResourceAddress(resourceAddress);
diff --git a/sdk/cosmos/azure-cosmos/src/main/java/com/azure/cosmos/CosmosException.java b/sdk/cosmos/azure-cosmos/src/main/java/com/azure/cosmos/CosmosException.java
index cb135b5cbcc9b..1a0ca50c055b3 100644
--- a/sdk/cosmos/azure-cosmos/src/main/java/com/azure/cosmos/CosmosException.java
+++ b/sdk/cosmos/azure-cosmos/src/main/java/com/azure/cosmos/CosmosException.java
@@ -44,7 +44,7 @@ public class CosmosException extends AzureException {
     private final Map<String, String> responseHeaders;
 
     private CosmosDiagnostics cosmosDiagnostics;
-    private final RequestTimeline requestTimeline;
+    private RequestTimeline requestTimeline;
     private CosmosError cosmosError;
 
     long lsn;
@@ -56,7 +56,6 @@ public class CosmosException extends AzureException {
     protected CosmosException(int statusCode, String message, Map<String, String> responseHeaders, Throwable cause) {
         super(message, cause);
         this.statusCode = statusCode;
-        this.requestTimeline = RequestTimeline.empty();
         this.responseHeaders = responseHeaders == null ? new HashMap<>() : new HashMap<>(responseHeaders);
     }
 
@@ -302,4 +301,12 @@ private List<Map.Entry<String, String>> filterSensitiveData(Map<String, String>
     void setResourceAddress(String resourceAddress) {
         this.resourceAddress = resourceAddress;
     }
+
+    RequestTimeline getRequestTimeline() {
+        return this.requestTimeline;
+    }
+
+    void setRequestTimeline(RequestTimeline requestTimeline) {
+        this.requestTimeline = requestTimeline;
+    }
 }
diff --git a/sdk/cosmos/azure-cosmos/src/main/java/com/azure/cosmos/implementation/directconnectivity/RntbdTransportClient.java b/sdk/cosmos/azure-cosmos/src/main/java/com/azure/cosmos/implementation/directconnectivity/RntbdTransportClient.java
index 8f14f5d276ef8..94c21155d0033 100644
--- a/sdk/cosmos/azure-cosmos/src/main/java/com/azure/cosmos/implementation/directconnectivity/RntbdTransportClient.java
+++ b/sdk/cosmos/azure-cosmos/src/main/java/com/azure/cosmos/implementation/directconnectivity/RntbdTransportClient.java
@@ -188,7 +188,11 @@ public Mono<StoreResponse> invokeStoreAsync(final Uri addressUri, final RxDocume
                     address.toString());
             }
 
-            return error;
+            assert error instanceof CosmosException;
+            CosmosException cosmosException = (CosmosException) error;
+            BridgeInternal.setRequestTimeline(cosmosException, record.takeTimelineSnapshot());
+
+            return cosmosException;
 
         });
 
diff --git a/sdk/cosmos/azure-cosmos/src/main/java/com/azure/cosmos/implementation/directconnectivity/StoreResult.java b/sdk/cosmos/azure-cosmos/src/main/java/com/azure/cosmos/implementation/directconnectivity/StoreResult.java
index 9d351b3838af2..785fa541864b8 100644
--- a/sdk/cosmos/azure-cosmos/src/main/java/com/azure/cosmos/implementation/directconnectivity/StoreResult.java
+++ b/sdk/cosmos/azure-cosmos/src/main/java/com/azure/cosmos/implementation/directconnectivity/StoreResult.java
@@ -196,7 +196,9 @@ public void serialize(StoreResult storeResult,
             jsonGenerator.writeNumberField("itemLSN", storeResult.itemLSN);
             jsonGenerator.writeStringField("sessionToken", (storeResult.sessionToken != null ? storeResult.sessionToken.convertToString() : null));
             jsonGenerator.writeStringField("exception", BridgeInternal.getInnerErrorMessage(storeResult.exception));
-            jsonGenerator.writeObjectField("transportRequestTimeline", storeResult.storeResponse != null ? storeResult.storeResponse.getRequestTimeline() : null);
+            jsonGenerator.writeObjectField("transportRequestTimeline", storeResult.storeResponse != null ?
+                storeResult.storeResponse.getRequestTimeline() :
+                storeResult.exception != null ? BridgeInternal.getRequestTimeline(storeResult.exception) : null);
             jsonGenerator.writeEndObject();
         }
     }
diff --git a/sdk/cosmos/azure-cosmos/src/test/java/com/azure/cosmos/CosmosDiagnosticsTest.java b/sdk/cosmos/azure-cosmos/src/test/java/com/azure/cosmos/CosmosDiagnosticsTest.java
index a4200e917bc5d..af1834398c51a 100644
--- a/sdk/cosmos/azure-cosmos/src/test/java/com/azure/cosmos/CosmosDiagnosticsTest.java
+++ b/sdk/cosmos/azure-cosmos/src/test/java/com/azure/cosmos/CosmosDiagnosticsTest.java
@@ -221,6 +221,14 @@ public void directDiagnostics() {
             assertThat(createResponse.getDiagnostics().getDuration()).isNotNull();
             validateTransportRequestTimelineDirect(diagnostics);
             validateJson(diagnostics);
+
+            // validate that on failed operation request timeline is populated
+            try {
+                cosmosContainer.createItem(internalObjectNode);
+                fail("expected 409");
+            } catch (CosmosException e) {
+                validateTransportRequestTimelineDirect(e.getDiagnostics().toString());
+            }
         } finally {
             if (testDirectClient != null) {
                 testDirectClient.close();
@@ -489,6 +497,9 @@ public void serializationOnVariousScenarios() {
         assertThat(diagnostics).contains("\"userAgent\":\"" + Utils.getUserAgent() + "\"");
     }
 
+
+
+
     @Test(groups = {"emulator"}, timeOut = TIMEOUT)
     public void addressResolutionStatistics() {
         CosmosClient client1 = null;