diff --git a/gradle/plugins/lifecycle-smoke-test-plugin/src/main/java/org/springframework/lifecycle/gradle/LifecycleSmokeTestPlugin.java b/gradle/plugins/lifecycle-smoke-test-plugin/src/main/java/org/springframework/lifecycle/gradle/LifecycleSmokeTestPlugin.java
index 7db1410..6a3d9ea 100644
--- a/gradle/plugins/lifecycle-smoke-test-plugin/src/main/java/org/springframework/lifecycle/gradle/LifecycleSmokeTestPlugin.java
+++ b/gradle/plugins/lifecycle-smoke-test-plugin/src/main/java/org/springframework/lifecycle/gradle/LifecycleSmokeTestPlugin.java
@@ -16,7 +16,9 @@
 
 package org.springframework.lifecycle.gradle;
 
+import java.util.ArrayList;
 import java.util.HashMap;
+import java.util.List;
 import java.util.Locale;
 import java.util.Map;
 import java.util.stream.Stream;
@@ -51,6 +53,8 @@ import org.springframework.lifecycle.gradle.tasks.StartApplication;
 import org.springframework.lifecycle.gradle.tasks.StartJvmApplication;
 import org.springframework.lifecycle.gradle.tasks.StopApplication;
 
+import static org.springframework.lifecycle.gradle.dsl.LifecycleSmokeTestExtension.*;
+
 /**
  * {@link Plugin} for a lifecycle smoke test project. Configures an {@code appTest} source
  * set and tasks for running the contained tests against the application running on the
@@ -103,16 +107,21 @@ public class LifecycleSmokeTestPlugin implements Plugin<Project> {
 		configureTests(project);
 		configureKotlin(project, javaExtension);
 		Provider<SmokeTest> smokeTestProvider = project.provider(() -> {
-			boolean runTests = false;
-			boolean runAppTests = false;
-			if (!javaExtension.getSourceSets().getByName(SourceSet.TEST_SOURCE_SET_NAME).getAllSource().isEmpty()) {
-				runTests = true;
+			boolean runTests = !javaExtension.getSourceSets().getByName(SourceSet.TEST_SOURCE_SET_NAME).getAllSource().isEmpty();
+			boolean runAppTests = !appTest.getAllSource().isEmpty();
+			List<String> expectedToFail = new ArrayList<>();
+			if (extension.getAppTest().getOutcome().get() == Outcome.FAILURE) {
+				expectedToFail.add("appTest");
 			}
-			if (!appTest.getAllSource().isEmpty()) {
-				runAppTests = true;
+			if (extension.getCheckpointRestoreAppTest().getOutcome().get() == Outcome.FAILURE) {
+				expectedToFail.add("checkpointRestoreAppTest");
 			}
+			if (extension.getTest().getOutcome().get() == Outcome.FAILURE) {
+				expectedToFail.add("test");
+			}
+
 			return new SmokeTest(project.getName(), project.getParent().getName(), project.getPath(), runTests,
-					runAppTests);
+					runAppTests, expectedToFail);
 		});
 		TaskProvider<DescribeSmokeTest> describeSmokeTest = project.getTasks()
 			.register("describeSmokeTest", DescribeSmokeTest.class);
diff --git a/gradle/plugins/lifecycle-smoke-test-plugin/src/main/java/org/springframework/lifecycle/gradle/dsl/LifecycleSmokeTestExtension.java b/gradle/plugins/lifecycle-smoke-test-plugin/src/main/java/org/springframework/lifecycle/gradle/dsl/LifecycleSmokeTestExtension.java
index 8de268b..6fd2857 100644
--- a/gradle/plugins/lifecycle-smoke-test-plugin/src/main/java/org/springframework/lifecycle/gradle/dsl/LifecycleSmokeTestExtension.java
+++ b/gradle/plugins/lifecycle-smoke-test-plugin/src/main/java/org/springframework/lifecycle/gradle/dsl/LifecycleSmokeTestExtension.java
@@ -18,7 +18,9 @@ package org.springframework.lifecycle.gradle.dsl;
 
 import javax.inject.Inject;
 
+import org.gradle.api.Action;
 import org.gradle.api.Project;
+import org.gradle.api.model.ObjectFactory;
 import org.gradle.api.provider.Property;
 
 /**
@@ -33,10 +35,21 @@ public class LifecycleSmokeTestExtension {
 
 	private final Property<String> checkpointEvent;
 
+	private final Expectation appTest;
+
+	private final Expectation checkpointRestoreAppTest;
+
+	private final Expectation test;
+
+
 	@Inject
 	public LifecycleSmokeTestExtension(Project project) {
-		this.webApplication = project.getObjects().property(Boolean.class);
-		this.checkpointEvent = project.getObjects().property(String.class);
+		ObjectFactory objects = project.getObjects();
+		this.webApplication = objects.property(Boolean.class);
+		this.checkpointEvent = objects.property(String.class);
+		this.appTest = objects.newInstance(Expectation.class, project);
+		this.checkpointRestoreAppTest = objects.newInstance(Expectation.class, project);
+		this.test = objects.newInstance(Expectation.class, project);
 	}
 
 	/**
@@ -55,4 +68,78 @@ public class LifecycleSmokeTestExtension {
 		return this.checkpointEvent;
 	}
 
+	/**
+	 * Expectations for {@code appTest}.
+	 */
+	public Expectation getAppTest() {
+		return this.appTest;
+	}
+
+	/**
+	 * Configure expectations for {@code appTest}.
+	 */
+	public void appTest(Action<Expectation> action) {
+		action.execute(this.appTest);
+	}
+
+	/**
+	 * Expectations for {@code checkpointRestoreAppTest}.
+	 */
+	public Expectation getCheckpointRestoreAppTest() {
+		return this.checkpointRestoreAppTest;
+	}
+
+	/**
+	 * Configure expectations for {@code checkpointRestoreAppTest}.
+	 */
+	public void checkpointRestoreAppTest(Action<Expectation> action) {
+		action.execute(this.checkpointRestoreAppTest);
+	}
+
+	/**
+	 * Expectations for {@code test}.
+	 */
+	public Expectation getTest() {
+		return this.test;
+	}
+
+	/**
+	 * Configure expectations for {@code test}.
+	 */
+	public void test(Action<Expectation> action) {
+		action.execute(this.test);
+	}
+
+	public static class Expectation {
+		private final Property<Outcome> outcome;
+		@Inject
+		public Expectation(Project project) {
+			this.outcome = project.getObjects().property(Outcome.class);
+			this.outcome.convention(Outcome.SUCCESS);
+		}
+		/**
+		 * The expected outcome.
+		 */
+		public Property<Outcome> getOutcome() {
+			return this.outcome;
+		}
+		/**
+		 * Note that expected outcome is failure
+		 */
+		public void expectedToFail(Action<Object> action) {
+			this.outcome.set(Outcome.FAILURE);
+		}
+	}
+	public static enum Outcome {
+		/**
+		 * The expected outcome is failure.
+		 */
+		FAILURE,
+		/**
+		 * The expected outcome is success.
+		 */
+		SUCCESS
+	}
+
+
 }
diff --git a/gradle/plugins/lifecycle-smoke-test-plugin/src/main/java/org/springframework/lifecycle/gradle/tasks/DescribeSmokeTest.java b/gradle/plugins/lifecycle-smoke-test-plugin/src/main/java/org/springframework/lifecycle/gradle/tasks/DescribeSmokeTest.java
index 70fa250..f9af976 100644
--- a/gradle/plugins/lifecycle-smoke-test-plugin/src/main/java/org/springframework/lifecycle/gradle/tasks/DescribeSmokeTest.java
+++ b/gradle/plugins/lifecycle-smoke-test-plugin/src/main/java/org/springframework/lifecycle/gradle/tasks/DescribeSmokeTest.java
@@ -59,6 +59,7 @@ public abstract class DescribeSmokeTest extends DefaultTask {
 		properties.add("path=" + smokeTest.path());
 		properties.add("group=" + smokeTest.group());
 		properties.add("name=" + smokeTest.name());
+		properties.add("expectedToFail=" + String.join(",", smokeTest.expectedToFail()));
 		Files.write(propertiesFile.toPath(), properties);
 	}
 
diff --git a/gradle/plugins/lifecycle-smoke-test-plugin/src/main/java/org/springframework/lifecycle/gradle/tasks/SmokeTest.java b/gradle/plugins/lifecycle-smoke-test-plugin/src/main/java/org/springframework/lifecycle/gradle/tasks/SmokeTest.java
index 3a8fa65..924637b 100644
--- a/gradle/plugins/lifecycle-smoke-test-plugin/src/main/java/org/springframework/lifecycle/gradle/tasks/SmokeTest.java
+++ b/gradle/plugins/lifecycle-smoke-test-plugin/src/main/java/org/springframework/lifecycle/gradle/tasks/SmokeTest.java
@@ -17,6 +17,7 @@
 package org.springframework.lifecycle.gradle.tasks;
 
 import java.io.Serializable;
+import java.util.List;
 import java.util.Properties;
 
 /**
@@ -30,11 +31,6 @@ import java.util.Properties;
  * @param appTests whether the smoke test contains any app tests
  */
 public record SmokeTest(String name, String group, String path, boolean tests,
-		boolean appTests) implements Serializable {
-
-	SmokeTest(Properties properties) {
-		this(properties.getProperty("name"), properties.getProperty("group"), properties.getProperty("path"),
-				Boolean.valueOf(properties.getProperty("tests")), Boolean.valueOf(properties.getProperty("appTests")));
-	}
+		boolean appTests, List<String> expectedToFail) implements Serializable {
 
 }