diff --git a/.github/trigger_files/beam_PreCommit_Python_PVR_Flink.json b/.github/trigger_files/beam_PreCommit_Python_PVR_Flink.json
new file mode 100644
index 000000000000..616d37428c01
--- /dev/null
+++ b/.github/trigger_files/beam_PreCommit_Python_PVR_Flink.json
@@ -0,0 +1,4 @@
+{
+    "comment": "Modify this file in a trivial way to cause this test suite to run",
+    "revision": 1
+}
diff --git a/sdks/java/core/src/main/java/org/apache/beam/sdk/options/PipelineOptionsFactory.java b/sdks/java/core/src/main/java/org/apache/beam/sdk/options/PipelineOptionsFactory.java
index ac76a57b6b07..b9061e1734cf 100644
--- a/sdks/java/core/src/main/java/org/apache/beam/sdk/options/PipelineOptionsFactory.java
+++ b/sdks/java/core/src/main/java/org/apache/beam/sdk/options/PipelineOptionsFactory.java
@@ -502,13 +502,6 @@ Class<T> getProxyClass() {
       new ObjectMapper()
           .registerModules(ObjectMapper.findModules(ReflectHelpers.findClassLoader()));
 
-  private static final DefaultDeserializationContext DESERIALIZATION_CONTEXT =
-      new DefaultDeserializationContext.Impl(MAPPER.getDeserializationContext().getFactory())
-          .createInstance(
-              MAPPER.getDeserializationConfig(),
-              new TokenBuffer(MAPPER, false).asParser(),
-              new InjectableValues.Std());
-
   static final DefaultSerializerProvider SERIALIZER_PROVIDER =
       new DefaultSerializerProvider.Impl()
           .createInstance(MAPPER.getSerializationConfig(), MAPPER.getSerializerFactory());
@@ -1733,7 +1726,12 @@ private static JsonDeserializer<Object> computeDeserializerForMethod(Method meth
       BeanProperty prop = createBeanProperty(method);
       AnnotatedMember annotatedMethod = prop.getMember();
 
-      DefaultDeserializationContext context = DESERIALIZATION_CONTEXT.copy();
+      // Initialize a new context that is properly associated with a dummy parser.
+      // Using copy() here would leave the context's transient parser field as null,
+      // causing NullPointerExceptions in Jackson 2.14+ when deserializers try to
+      // query the parser for format constraints or coercion validations.
+      JsonParser dummyParser = new TokenBuffer(MAPPER, false).asParser();
+      DefaultDeserializationContext context = createDeserializationContext(dummyParser);
       Object maybeDeserializerClass =
           context.getAnnotationIntrospector().findDeserializer(annotatedMethod);
 
@@ -1756,6 +1754,11 @@ private static JsonDeserializer<Object> computeDeserializerForMethod(Method meth
     }
   }
 
+  private static DefaultDeserializationContext createDeserializationContext(JsonParser parser) {
+    return ((DefaultDeserializationContext) MAPPER.getDeserializationContext())
+        .createInstance(MAPPER.getDeserializationConfig(), parser, new InjectableValues.Std());
+  }
+
   private static Optional<JsonSerializer<Object>> computeCustomSerializerForMethod(Method method) {
     try {
       BeanProperty prop = createBeanProperty(method);
@@ -1805,7 +1808,12 @@ static Object deserializeNode(JsonNode node, Method method) throws IOException {
     parser.nextToken();
 
     JsonDeserializer<Object> jsonDeserializer = getDeserializerForMethod(method);
-    return jsonDeserializer.deserialize(parser, DESERIALIZATION_CONTEXT.copy());
+    // Create a fresh context that is correctly associated with the active parser.
+    // Using copy() here would leave the context's transient parser field as null,
+    // causing NullPointerExceptions in Jackson 2.14+ deserializers during coercion
+    // validations and length checks.
+    DefaultDeserializationContext context = createDeserializationContext(parser);
+    return jsonDeserializer.deserialize(parser, context);
   }
 
   /**