diff --git a/avro/src/test/java/com/fasterxml/jackson/dataformat/avro/testutil/failure/JacksonTestFailureExpected.java b/avro/src/test/java/com/fasterxml/jackson/dataformat/avro/testutil/failure/JacksonTestFailureExpected.java
new file mode 100644
index 000000000..20c81274a
--- /dev/null
+++ b/avro/src/test/java/com/fasterxml/jackson/dataformat/avro/testutil/failure/JacksonTestFailureExpected.java
@@ -0,0 +1,38 @@
+package com.fasterxml.jackson.dataformat.avro.testutil.failure;
+
+import java.lang.annotation.*;
+
+import org.junit.jupiter.api.extension.ExtendWith;
+
+/**
+ * <p>
+ * Annotation used to indicate that a JUnit-5 based tests method is expected to fail.
+ *
+ * <p>
+ * When a test method is annotated with {@code @JacksonTestFailureExpected}, the
+ * {@link JacksonTestFailureExpectedInterceptor} will intercept the test execution.
+ * If the test passes, which is an unexpected behavior, the interceptor will throw an exception to fail the test,
+ * indicating that the test was expected to fail but didn't.
+ * </p>
+ *
+ * <h3>Usage Example:</h3>
+ *
+ * <pre><code>
+ *
+ *     &#64;Test
+ *     &#64;JacksonTestFailureExpected
+ *     @Test
+    public void testFeatureNotYetImplemented() {
+ *         // Test code that is expected to fail
+ *     }
+ * }
+ * </code></pre>
+ *
+ * <p>
+ *
+ * @since 2.19
+ */
+@Target({ElementType.METHOD})
+@Retention(RetentionPolicy.RUNTIME)
+@ExtendWith(JacksonTestFailureExpectedInterceptor.class)
+public @interface JacksonTestFailureExpected { }
diff --git a/avro/src/test/java/com/fasterxml/jackson/dataformat/avro/testutil/failure/JacksonTestFailureExpectedInterceptor.java b/avro/src/test/java/com/fasterxml/jackson/dataformat/avro/testutil/failure/JacksonTestFailureExpectedInterceptor.java
new file mode 100644
index 000000000..1284841ca
--- /dev/null
+++ b/avro/src/test/java/com/fasterxml/jackson/dataformat/avro/testutil/failure/JacksonTestFailureExpectedInterceptor.java
@@ -0,0 +1,43 @@
+package com.fasterxml.jackson.dataformat.avro.testutil.failure;
+
+import java.lang.reflect.Method;
+
+import org.junit.jupiter.api.extension.*;
+
+/**
+ * Custom {@link InvocationInterceptor} that intercepts test method invocation.
+ * To pass the test ***only if*** test fails with an exception, and fail the test otherwise.
+ *
+ * @since 2.19
+ */
+public class JacksonTestFailureExpectedInterceptor
+    implements InvocationInterceptor
+{
+    @Override
+    public void interceptTestMethod(Invocation<Void> invocation,
+            ReflectiveInvocationContext<Method> invocationContext, ExtensionContext extensionContext)
+        throws Throwable
+    {
+        try {
+            invocation.proceed();
+        } catch (Throwable t) {
+            // do-nothing, we do expect an exception
+            return;
+        }
+        handleUnexpectePassingTest(invocationContext);
+    }
+
+    private void handleUnexpectePassingTest(ReflectiveInvocationContext<Method> invocationContext) {
+        // Collect information we need
+        Object targetClass = invocationContext.getTargetClass();
+        Object testMethod = invocationContext.getExecutable().getName();
+        //List<Object> arguments = invocationContext.getArguments();
+
+        // Create message
+        String message = String.format("Test method %s.%s() passed, but should have failed", targetClass, testMethod);
+
+        // throw exception
+        throw new JacksonTestShouldFailException(message);
+    }
+
+}
diff --git a/avro/src/test/java/com/fasterxml/jackson/dataformat/avro/testutil/failure/JacksonTestShouldFailException.java b/avro/src/test/java/com/fasterxml/jackson/dataformat/avro/testutil/failure/JacksonTestShouldFailException.java
new file mode 100644
index 000000000..ec35d7899
--- /dev/null
+++ b/avro/src/test/java/com/fasterxml/jackson/dataformat/avro/testutil/failure/JacksonTestShouldFailException.java
@@ -0,0 +1,18 @@
+package com.fasterxml.jackson.dataformat.avro.testutil.failure;
+
+/**
+ * Exception used to alert that a test is passing, but should be failing.
+ *
+ * WARNING : This only for test code, and should never be thrown from production code.
+ *
+ * @since 2.19
+ */
+public class JacksonTestShouldFailException
+    extends RuntimeException
+{
+    private static final long serialVersionUID = 1L;
+
+    public JacksonTestShouldFailException(String msg) {
+        super(msg);
+    }
+}
diff --git a/cbor/src/test/java/com/fasterxml/jackson/dataformat/cbor/testutil/failure/JacksonTestFailureExpected.java b/cbor/src/test/java/com/fasterxml/jackson/dataformat/cbor/testutil/failure/JacksonTestFailureExpected.java
new file mode 100644
index 000000000..571b28b5d
--- /dev/null
+++ b/cbor/src/test/java/com/fasterxml/jackson/dataformat/cbor/testutil/failure/JacksonTestFailureExpected.java
@@ -0,0 +1,38 @@
+package com.fasterxml.jackson.dataformat.cbor.testutil.failure;
+
+import java.lang.annotation.*;
+
+import org.junit.jupiter.api.extension.ExtendWith;
+
+/**
+ * <p>
+ * Annotation used to indicate that a JUnit-5 based tests method is expected to fail.
+ *
+ * <p>
+ * When a test method is annotated with {@code @JacksonTestFailureExpected}, the
+ * {@link JacksonTestFailureExpectedInterceptor} will intercept the test execution.
+ * If the test passes, which is an unexpected behavior, the interceptor will throw an exception to fail the test,
+ * indicating that the test was expected to fail but didn't.
+ * </p>
+ *
+ * <h3>Usage Example:</h3>
+ *
+ * <pre><code>
+ *
+ *     &#64;Test
+ *     &#64;JacksonTestFailureExpected
+ *     @Test
+    public void testFeatureNotYetImplemented() {
+ *         // Test code that is expected to fail
+ *     }
+ * }
+ * </code></pre>
+ *
+ * <p>
+ *
+ * @since 2.19
+ */
+@Target({ElementType.METHOD})
+@Retention(RetentionPolicy.RUNTIME)
+@ExtendWith(JacksonTestFailureExpectedInterceptor.class)
+public @interface JacksonTestFailureExpected { }
diff --git a/cbor/src/test/java/com/fasterxml/jackson/dataformat/cbor/testutil/failure/JacksonTestFailureExpectedInterceptor.java b/cbor/src/test/java/com/fasterxml/jackson/dataformat/cbor/testutil/failure/JacksonTestFailureExpectedInterceptor.java
new file mode 100644
index 000000000..47d9f23a7
--- /dev/null
+++ b/cbor/src/test/java/com/fasterxml/jackson/dataformat/cbor/testutil/failure/JacksonTestFailureExpectedInterceptor.java
@@ -0,0 +1,43 @@
+package com.fasterxml.jackson.dataformat.cbor.testutil.failure;
+
+import java.lang.reflect.Method;
+
+import org.junit.jupiter.api.extension.*;
+
+/**
+ * Custom {@link InvocationInterceptor} that intercepts test method invocation.
+ * To pass the test ***only if*** test fails with an exception, and fail the test otherwise.
+ *
+ * @since 2.19
+ */
+public class JacksonTestFailureExpectedInterceptor
+    implements InvocationInterceptor
+{
+    @Override
+    public void interceptTestMethod(Invocation<Void> invocation,
+            ReflectiveInvocationContext<Method> invocationContext, ExtensionContext extensionContext)
+        throws Throwable
+    {
+        try {
+            invocation.proceed();
+        } catch (Throwable t) {
+            // do-nothing, we do expect an exception
+            return;
+        }
+        handleUnexpectePassingTest(invocationContext);
+    }
+
+    private void handleUnexpectePassingTest(ReflectiveInvocationContext<Method> invocationContext) {
+        // Collect information we need
+        Object targetClass = invocationContext.getTargetClass();
+        Object testMethod = invocationContext.getExecutable().getName();
+        //List<Object> arguments = invocationContext.getArguments();
+
+        // Create message
+        String message = String.format("Test method %s.%s() passed, but should have failed", targetClass, testMethod);
+
+        // throw exception
+        throw new JacksonTestShouldFailException(message);
+    }
+
+}
diff --git a/cbor/src/test/java/com/fasterxml/jackson/dataformat/cbor/testutil/failure/JacksonTestShouldFailException.java b/cbor/src/test/java/com/fasterxml/jackson/dataformat/cbor/testutil/failure/JacksonTestShouldFailException.java
new file mode 100644
index 000000000..e74611237
--- /dev/null
+++ b/cbor/src/test/java/com/fasterxml/jackson/dataformat/cbor/testutil/failure/JacksonTestShouldFailException.java
@@ -0,0 +1,18 @@
+package com.fasterxml.jackson.dataformat.cbor.testutil.failure;
+
+/**
+ * Exception used to alert that a test is passing, but should be failing.
+ *
+ * WARNING : This only for test code, and should never be thrown from production code.
+ *
+ * @since 2.19
+ */
+public class JacksonTestShouldFailException
+    extends RuntimeException
+{
+    private static final long serialVersionUID = 1L;
+
+    public JacksonTestShouldFailException(String msg) {
+        super(msg);
+    }
+}
diff --git a/ion/src/test/java/com/fasterxml/jackson/dataformat/ion/testutil/failure/JacksonTestFailureExpected.java b/ion/src/test/java/com/fasterxml/jackson/dataformat/ion/testutil/failure/JacksonTestFailureExpected.java
new file mode 100644
index 000000000..86839a72f
--- /dev/null
+++ b/ion/src/test/java/com/fasterxml/jackson/dataformat/ion/testutil/failure/JacksonTestFailureExpected.java
@@ -0,0 +1,38 @@
+package com.fasterxml.jackson.dataformat.ion.testutil.failure;
+
+import java.lang.annotation.*;
+
+import org.junit.jupiter.api.extension.ExtendWith;
+
+/**
+ * <p>
+ * Annotation used to indicate that a JUnit-5 based tests method is expected to fail.
+ *
+ * <p>
+ * When a test method is annotated with {@code @JacksonTestFailureExpected}, the
+ * {@link JacksonTestFailureExpectedInterceptor} will intercept the test execution.
+ * If the test passes, which is an unexpected behavior, the interceptor will throw an exception to fail the test,
+ * indicating that the test was expected to fail but didn't.
+ * </p>
+ *
+ * <h3>Usage Example:</h3>
+ *
+ * <pre><code>
+ *
+ *     &#64;Test
+ *     &#64;JacksonTestFailureExpected
+ *     @Test
+    public void testFeatureNotYetImplemented() {
+ *         // Test code that is expected to fail
+ *     }
+ * }
+ * </code></pre>
+ *
+ * <p>
+ *
+ * @since 2.19
+ */
+@Target({ElementType.METHOD})
+@Retention(RetentionPolicy.RUNTIME)
+@ExtendWith(JacksonTestFailureExpectedInterceptor.class)
+public @interface JacksonTestFailureExpected { }
diff --git a/ion/src/test/java/com/fasterxml/jackson/dataformat/ion/testutil/failure/JacksonTestFailureExpectedInterceptor.java b/ion/src/test/java/com/fasterxml/jackson/dataformat/ion/testutil/failure/JacksonTestFailureExpectedInterceptor.java
new file mode 100644
index 000000000..9724649e5
--- /dev/null
+++ b/ion/src/test/java/com/fasterxml/jackson/dataformat/ion/testutil/failure/JacksonTestFailureExpectedInterceptor.java
@@ -0,0 +1,43 @@
+package com.fasterxml.jackson.dataformat.ion.testutil.failure;
+
+import java.lang.reflect.Method;
+
+import org.junit.jupiter.api.extension.*;
+
+/**
+ * Custom {@link InvocationInterceptor} that intercepts test method invocation.
+ * To pass the test ***only if*** test fails with an exception, and fail the test otherwise.
+ *
+ * @since 2.19
+ */
+public class JacksonTestFailureExpectedInterceptor
+    implements InvocationInterceptor
+{
+    @Override
+    public void interceptTestMethod(Invocation<Void> invocation,
+            ReflectiveInvocationContext<Method> invocationContext, ExtensionContext extensionContext)
+        throws Throwable
+    {
+        try {
+            invocation.proceed();
+        } catch (Throwable t) {
+            // do-nothing, we do expect an exception
+            return;
+        }
+        handleUnexpectePassingTest(invocationContext);
+    }
+
+    private void handleUnexpectePassingTest(ReflectiveInvocationContext<Method> invocationContext) {
+        // Collect information we need
+        Object targetClass = invocationContext.getTargetClass();
+        Object testMethod = invocationContext.getExecutable().getName();
+        //List<Object> arguments = invocationContext.getArguments();
+
+        // Create message
+        String message = String.format("Test method %s.%s() passed, but should have failed", targetClass, testMethod);
+
+        // throw exception
+        throw new JacksonTestShouldFailException(message);
+    }
+
+}
diff --git a/ion/src/test/java/com/fasterxml/jackson/dataformat/ion/testutil/failure/JacksonTestShouldFailException.java b/ion/src/test/java/com/fasterxml/jackson/dataformat/ion/testutil/failure/JacksonTestShouldFailException.java
new file mode 100644
index 000000000..3d1ef99de
--- /dev/null
+++ b/ion/src/test/java/com/fasterxml/jackson/dataformat/ion/testutil/failure/JacksonTestShouldFailException.java
@@ -0,0 +1,18 @@
+package com.fasterxml.jackson.dataformat.ion.testutil.failure;
+
+/**
+ * Exception used to alert that a test is passing, but should be failing.
+ *
+ * WARNING : This only for test code, and should never be thrown from production code.
+ *
+ * @since 2.19
+ */
+public class JacksonTestShouldFailException
+    extends RuntimeException
+{
+    private static final long serialVersionUID = 1L;
+
+    public JacksonTestShouldFailException(String msg) {
+        super(msg);
+    }
+}
diff --git a/pom.xml b/pom.xml
index f9cb18d33..9b50e0f52 100644
--- a/pom.xml
+++ b/pom.xml
@@ -67,7 +67,18 @@
       <groupId>junit</groupId>
       <artifactId>junit</artifactId>
       <scope>test</scope>
-    </dependency>    
+    </dependency>
+    <!-- 11-Jan-2025, joohyukkim: For JSTEP-10, migrate to JUnit5 -->
+    <dependency>
+      <groupId>org.junit.jupiter</groupId>
+      <artifactId>junit-jupiter</artifactId>
+      <scope>test</scope>
+    </dependency>
+    <dependency>
+      <groupId>org.junit.jupiter</groupId>
+      <artifactId>junit-jupiter-api</artifactId>
+      <scope>test</scope>
+    </dependency>
   </dependencies>
 
   <!-- Alas, need to include snapshot reference since otherwise can not find
diff --git a/protobuf/src/test/java/com/fasterxml/jackson/dataformat/protobuf/testutil/failure/JacksonTestFailureExpected.java b/protobuf/src/test/java/com/fasterxml/jackson/dataformat/protobuf/testutil/failure/JacksonTestFailureExpected.java
new file mode 100644
index 000000000..84d102e5f
--- /dev/null
+++ b/protobuf/src/test/java/com/fasterxml/jackson/dataformat/protobuf/testutil/failure/JacksonTestFailureExpected.java
@@ -0,0 +1,38 @@
+package com.fasterxml.jackson.dataformat.protobuf.testutil.failure;
+
+import java.lang.annotation.*;
+
+import org.junit.jupiter.api.extension.ExtendWith;
+
+/**
+ * <p>
+ * Annotation used to indicate that a JUnit-5 based tests method is expected to fail.
+ *
+ * <p>
+ * When a test method is annotated with {@code @JacksonTestFailureExpected}, the
+ * {@link JacksonTestFailureExpectedInterceptor} will intercept the test execution.
+ * If the test passes, which is an unexpected behavior, the interceptor will throw an exception to fail the test,
+ * indicating that the test was expected to fail but didn't.
+ * </p>
+ *
+ * <h3>Usage Example:</h3>
+ *
+ * <pre><code>
+ *
+ *     &#64;Test
+ *     &#64;JacksonTestFailureExpected
+ *     @Test
+    public void testFeatureNotYetImplemented() {
+ *         // Test code that is expected to fail
+ *     }
+ * }
+ * </code></pre>
+ *
+ * <p>
+ *
+ * @since 2.19
+ */
+@Target({ElementType.METHOD})
+@Retention(RetentionPolicy.RUNTIME)
+@ExtendWith(JacksonTestFailureExpectedInterceptor.class)
+public @interface JacksonTestFailureExpected { }
diff --git a/protobuf/src/test/java/com/fasterxml/jackson/dataformat/protobuf/testutil/failure/JacksonTestFailureExpectedInterceptor.java b/protobuf/src/test/java/com/fasterxml/jackson/dataformat/protobuf/testutil/failure/JacksonTestFailureExpectedInterceptor.java
new file mode 100644
index 000000000..98c17aad2
--- /dev/null
+++ b/protobuf/src/test/java/com/fasterxml/jackson/dataformat/protobuf/testutil/failure/JacksonTestFailureExpectedInterceptor.java
@@ -0,0 +1,43 @@
+package com.fasterxml.jackson.dataformat.protobuf.testutil.failure;
+
+import java.lang.reflect.Method;
+
+import org.junit.jupiter.api.extension.*;
+
+/**
+ * Custom {@link InvocationInterceptor} that intercepts test method invocation.
+ * To pass the test ***only if*** test fails with an exception, and fail the test otherwise.
+ *
+ * @since 2.19
+ */
+public class JacksonTestFailureExpectedInterceptor
+    implements InvocationInterceptor
+{
+    @Override
+    public void interceptTestMethod(Invocation<Void> invocation,
+            ReflectiveInvocationContext<Method> invocationContext, ExtensionContext extensionContext)
+        throws Throwable
+    {
+        try {
+            invocation.proceed();
+        } catch (Throwable t) {
+            // do-nothing, we do expect an exception
+            return;
+        }
+        handleUnexpectePassingTest(invocationContext);
+    }
+
+    private void handleUnexpectePassingTest(ReflectiveInvocationContext<Method> invocationContext) {
+        // Collect information we need
+        Object targetClass = invocationContext.getTargetClass();
+        Object testMethod = invocationContext.getExecutable().getName();
+        //List<Object> arguments = invocationContext.getArguments();
+
+        // Create message
+        String message = String.format("Test method %s.%s() passed, but should have failed", targetClass, testMethod);
+
+        // throw exception
+        throw new JacksonTestShouldFailException(message);
+    }
+
+}
diff --git a/protobuf/src/test/java/com/fasterxml/jackson/dataformat/protobuf/testutil/failure/JacksonTestShouldFailException.java b/protobuf/src/test/java/com/fasterxml/jackson/dataformat/protobuf/testutil/failure/JacksonTestShouldFailException.java
new file mode 100644
index 000000000..369600cca
--- /dev/null
+++ b/protobuf/src/test/java/com/fasterxml/jackson/dataformat/protobuf/testutil/failure/JacksonTestShouldFailException.java
@@ -0,0 +1,18 @@
+package com.fasterxml.jackson.dataformat.protobuf.testutil.failure;
+
+/**
+ * Exception used to alert that a test is passing, but should be failing.
+ *
+ * WARNING : This only for test code, and should never be thrown from production code.
+ *
+ * @since 2.19
+ */
+public class JacksonTestShouldFailException
+    extends RuntimeException
+{
+    private static final long serialVersionUID = 1L;
+
+    public JacksonTestShouldFailException(String msg) {
+        super(msg);
+    }
+}
diff --git a/smile/src/test/java/com/fasterxml/jackson/dataformat/smile/testutil/failure/JacksonTestFailureExpected.java b/smile/src/test/java/com/fasterxml/jackson/dataformat/smile/testutil/failure/JacksonTestFailureExpected.java
new file mode 100644
index 000000000..3457afd66
--- /dev/null
+++ b/smile/src/test/java/com/fasterxml/jackson/dataformat/smile/testutil/failure/JacksonTestFailureExpected.java
@@ -0,0 +1,38 @@
+package com.fasterxml.jackson.dataformat.smile.testutil.failure;
+
+import java.lang.annotation.*;
+
+import org.junit.jupiter.api.extension.ExtendWith;
+
+/**
+ * <p>
+ * Annotation used to indicate that a JUnit-5 based tests method is expected to fail.
+ *
+ * <p>
+ * When a test method is annotated with {@code @JacksonTestFailureExpected}, the
+ * {@link JacksonTestFailureExpectedInterceptor} will intercept the test execution.
+ * If the test passes, which is an unexpected behavior, the interceptor will throw an exception to fail the test,
+ * indicating that the test was expected to fail but didn't.
+ * </p>
+ *
+ * <h3>Usage Example:</h3>
+ *
+ * <pre><code>
+ *
+ *     &#64;Test
+ *     &#64;JacksonTestFailureExpected
+ *     @Test
+    public void testFeatureNotYetImplemented() {
+ *         // Test code that is expected to fail
+ *     }
+ * }
+ * </code></pre>
+ *
+ * <p>
+ *
+ * @since 2.19
+ */
+@Target({ElementType.METHOD})
+@Retention(RetentionPolicy.RUNTIME)
+@ExtendWith(JacksonTestFailureExpectedInterceptor.class)
+public @interface JacksonTestFailureExpected { }
diff --git a/smile/src/test/java/com/fasterxml/jackson/dataformat/smile/testutil/failure/JacksonTestFailureExpectedInterceptor.java b/smile/src/test/java/com/fasterxml/jackson/dataformat/smile/testutil/failure/JacksonTestFailureExpectedInterceptor.java
new file mode 100644
index 000000000..110cdcb04
--- /dev/null
+++ b/smile/src/test/java/com/fasterxml/jackson/dataformat/smile/testutil/failure/JacksonTestFailureExpectedInterceptor.java
@@ -0,0 +1,43 @@
+package com.fasterxml.jackson.dataformat.smile.testutil.failure;
+
+import java.lang.reflect.Method;
+
+import org.junit.jupiter.api.extension.*;
+
+/**
+ * Custom {@link InvocationInterceptor} that intercepts test method invocation.
+ * To pass the test ***only if*** test fails with an exception, and fail the test otherwise.
+ *
+ * @since 2.19
+ */
+public class JacksonTestFailureExpectedInterceptor
+    implements InvocationInterceptor
+{
+    @Override
+    public void interceptTestMethod(Invocation<Void> invocation,
+            ReflectiveInvocationContext<Method> invocationContext, ExtensionContext extensionContext)
+        throws Throwable
+    {
+        try {
+            invocation.proceed();
+        } catch (Throwable t) {
+            // do-nothing, we do expect an exception
+            return;
+        }
+        handleUnexpectePassingTest(invocationContext);
+    }
+
+    private void handleUnexpectePassingTest(ReflectiveInvocationContext<Method> invocationContext) {
+        // Collect information we need
+        Object targetClass = invocationContext.getTargetClass();
+        Object testMethod = invocationContext.getExecutable().getName();
+        //List<Object> arguments = invocationContext.getArguments();
+
+        // Create message
+        String message = String.format("Test method %s.%s() passed, but should have failed", targetClass, testMethod);
+
+        // throw exception
+        throw new JacksonTestShouldFailException(message);
+    }
+
+}
diff --git a/smile/src/test/java/com/fasterxml/jackson/dataformat/smile/testutil/failure/JacksonTestShouldFailException.java b/smile/src/test/java/com/fasterxml/jackson/dataformat/smile/testutil/failure/JacksonTestShouldFailException.java
new file mode 100644
index 000000000..9a174e243
--- /dev/null
+++ b/smile/src/test/java/com/fasterxml/jackson/dataformat/smile/testutil/failure/JacksonTestShouldFailException.java
@@ -0,0 +1,18 @@
+package com.fasterxml.jackson.dataformat.smile.testutil.failure;
+
+/**
+ * Exception used to alert that a test is passing, but should be failing.
+ *
+ * WARNING : This only for test code, and should never be thrown from production code.
+ *
+ * @since 2.19
+ */
+public class JacksonTestShouldFailException
+    extends RuntimeException
+{
+    private static final long serialVersionUID = 1L;
+
+    public JacksonTestShouldFailException(String msg) {
+        super(msg);
+    }
+}