diff --git a/src/main/java/com/fasterxml/jackson/datatype/jdk8/OptionalSerializer.java b/src/main/java/com/fasterxml/jackson/datatype/jdk8/OptionalSerializer.java
index 86a5be3..aa755af 100644
--- a/src/main/java/com/fasterxml/jackson/datatype/jdk8/OptionalSerializer.java
+++ b/src/main/java/com/fasterxml/jackson/datatype/jdk8/OptionalSerializer.java
@@ -315,6 +315,7 @@ private final JsonSerializer<Object> _findCachedSerializer(SerializerProvider pr
             }
             _dynamicSerializers = _dynamicSerializers.newWith(type, ser);
         }
+        ser = (JsonSerializer<Object>)provider.handlePrimaryContextualization(ser, _property);
         return ser;
     }