diff --git a/sdk/core/azure-core-serializer-json-jackson/src/main/java/com/azure/core/serializer/json/jackson/implementation/ObjectMapperShim.java b/sdk/core/azure-core-serializer-json-jackson/src/main/java/com/azure/core/serializer/json/jackson/implementation/ObjectMapperShim.java
index 0ba4f95ca0a7b..7b772355ec1cd 100644
--- a/sdk/core/azure-core-serializer-json-jackson/src/main/java/com/azure/core/serializer/json/jackson/implementation/ObjectMapperShim.java
+++ b/sdk/core/azure-core-serializer-json-jackson/src/main/java/com/azure/core/serializer/json/jackson/implementation/ObjectMapperShim.java
@@ -6,10 +6,12 @@
 import com.azure.core.annotation.HeaderCollection;
 import com.azure.core.http.HttpHeader;
 import com.azure.core.http.HttpHeaders;
-import com.azure.core.implementation.ReflectiveInvoker;
+import com.azure.core.implementation.ReflectionSerializable;
 import com.azure.core.implementation.ReflectionUtils;
+import com.azure.core.implementation.ReflectiveInvoker;
 import com.azure.core.implementation.TypeUtil;
 import com.azure.core.util.logging.ClientLogger;
+import com.azure.json.JsonSerializable;
 import com.fasterxml.jackson.databind.JavaType;
 import com.fasterxml.jackson.databind.JsonNode;
 import com.fasterxml.jackson.databind.ObjectMapper;
@@ -264,6 +266,7 @@ public JsonNode readTree(byte[] content) throws IOException {
         }
     }
 
+    @SuppressWarnings("unchecked")
     private JavaType createJavaType(Type type) {
         if (type == null) {
             return null;
@@ -280,7 +283,28 @@ private JavaType createJavaType(Type type) {
             return getFromTypeCache(type, t -> mapper.getTypeFactory()
                 .constructParametricType((Class<?>) parameterizedType.getRawType(), javaTypeArguments));
         } else {
-            return getFromTypeCache(type, t -> mapper.getTypeFactory().constructType(t));
+            return getFromTypeCache(type, t -> {
+                JavaType javaType = mapper.constructType(t);
+
+                // Need additional handling here so that the JavaType returned has the correct value handler for
+                // JsonSerializable types.
+                // While JsonSerializableDeserializer is registered with the ObjectMapper, and it mutates the
+                // JsonSerializer used by Jackson to handle as a JsonSerializable type, there have been cases where
+                // collection types (List, Map, etc) have not been handled correctly. So, additional handling is done
+                // here to ensure that the JavaType returned has the correct value handler.
+
+                if (!(t instanceof Class<?>)) {
+                    // Not a Class, so can't be a JsonSerializable type.
+                    return javaType;
+                }
+
+                if (ReflectionSerializable.supportsJsonSerializable((Class<?>) t)) {
+                    // JsonSerializable type, so add the JsonSerializableDeserializer as the value handler.
+                    return javaType.withValueHandler(new JsonSerializableDeserializer((Class<JsonSerializable<?>>) t));
+                }
+
+                return javaType;
+            });
         }
     }
 
diff --git a/sdk/core/azure-core/src/main/java/com/azure/core/implementation/jackson/ObjectMapperShim.java b/sdk/core/azure-core/src/main/java/com/azure/core/implementation/jackson/ObjectMapperShim.java
index b6a7af7a63724..4a2c2ac214cb1 100644
--- a/sdk/core/azure-core/src/main/java/com/azure/core/implementation/jackson/ObjectMapperShim.java
+++ b/sdk/core/azure-core/src/main/java/com/azure/core/implementation/jackson/ObjectMapperShim.java
@@ -6,12 +6,14 @@
 import com.azure.core.annotation.HeaderCollection;
 import com.azure.core.http.HttpHeader;
 import com.azure.core.http.HttpHeaders;
+import com.azure.core.implementation.ReflectionSerializable;
 import com.azure.core.implementation.ReflectionUtils;
 import com.azure.core.implementation.ReflectiveInvoker;
 import com.azure.core.implementation.TypeUtil;
 import com.azure.core.util.logging.ClientLogger;
 import com.azure.core.util.logging.LogLevel;
 import com.azure.core.util.serializer.MemberNameConverter;
+import com.azure.json.JsonSerializable;
 import com.fasterxml.jackson.databind.JavaType;
 import com.fasterxml.jackson.databind.JsonNode;
 import com.fasterxml.jackson.databind.ObjectMapper;
@@ -294,6 +296,7 @@ public JsonNode readTree(byte[] content) throws IOException {
         }
     }
 
+    @SuppressWarnings("unchecked")
     private JavaType createJavaType(Type type) {
         if (type == null) {
             return null;
@@ -310,7 +313,28 @@ private JavaType createJavaType(Type type) {
             return getFromTypeCache(type, t -> mapper.getTypeFactory()
                 .constructParametricType((Class<?>) parameterizedType.getRawType(), javaTypeArguments));
         } else {
-            return getFromTypeCache(type, t -> mapper.getTypeFactory().constructType(t));
+            return getFromTypeCache(type, t -> {
+                JavaType javaType = mapper.constructType(t);
+
+                // Need additional handling here so that the JavaType returned has the correct value handler for
+                // JsonSerializable types.
+                // While JsonSerializableDeserializer is registered with the ObjectMapper, and it mutates the
+                // JsonSerializer used by Jackson to handle as a JsonSerializable type, there have been cases where
+                // collection types (List, Map, etc) have not been handled correctly. So, additional handling is done
+                // here to ensure that the JavaType returned has the correct value handler.
+
+                if (!(t instanceof Class<?>)) {
+                    // Not a Class, so can't be a JsonSerializable type.
+                    return javaType;
+                }
+
+                if (ReflectionSerializable.supportsJsonSerializable((Class<?>) t)) {
+                    // JsonSerializable type, so add the JsonSerializableDeserializer as the value handler.
+                    return javaType.withValueHandler(new JsonSerializableDeserializer((Class<JsonSerializable<?>>) t));
+                }
+
+                return javaType;
+            });
         }
     }