diff --git a/spring-boot-test-autoconfigure/src/main/java/org/springframework/boot/test/autoconfigure/SpringBootDependencyInjectionTestExecutionListener.java b/spring-boot-test-autoconfigure/src/main/java/org/springframework/boot/test/autoconfigure/SpringBootDependencyInjectionTestExecutionListener.java
index 55d8a3555c..a9c93776b4 100644
--- a/spring-boot-test-autoconfigure/src/main/java/org/springframework/boot/test/autoconfigure/SpringBootDependencyInjectionTestExecutionListener.java
+++ b/spring-boot-test-autoconfigure/src/main/java/org/springframework/boot/test/autoconfigure/SpringBootDependencyInjectionTestExecutionListener.java
@@ -44,13 +44,22 @@ public class SpringBootDependencyInjectionTestExecutionListener
 			super.prepareTestInstance(testContext);
 		}
 		catch (Exception ex) {
+			outputConditionEvaluationReport(testContext);
+			throw ex;
+		}
+	}
+
+	private void outputConditionEvaluationReport(TestContext testContext) {
+		try {
 			ApplicationContext context = testContext.getApplicationContext();
 			if (context instanceof ConfigurableApplicationContext) {
 				ConditionEvaluationReport report = ConditionEvaluationReport
 						.get(((ConfigurableApplicationContext) context).getBeanFactory());
 				System.err.println(new ConditionEvaluationReportMessage(report));
 			}
-			throw ex;
+		}
+		catch (Exception ex) {
+			// Allow original failure to be reported
 		}
 	}
 
diff --git a/spring-boot-test-autoconfigure/src/test/java/org/springframework/boot/test/autoconfigure/SpringBootDependencyInjectionTestExecutionListenerTests.java b/spring-boot-test-autoconfigure/src/test/java/org/springframework/boot/test/autoconfigure/SpringBootDependencyInjectionTestExecutionListenerTests.java
index edb70bf96a..66529936db 100644
--- a/spring-boot-test-autoconfigure/src/test/java/org/springframework/boot/test/autoconfigure/SpringBootDependencyInjectionTestExecutionListenerTests.java
+++ b/spring-boot-test-autoconfigure/src/test/java/org/springframework/boot/test/autoconfigure/SpringBootDependencyInjectionTestExecutionListenerTests.java
@@ -18,6 +18,7 @@ package org.springframework.boot.test.autoconfigure;
 
 import org.junit.Rule;
 import org.junit.Test;
+import org.junit.rules.ExpectedException;
 
 import org.springframework.boot.SpringApplication;
 import org.springframework.boot.WebApplicationType;
@@ -31,6 +32,7 @@ import org.springframework.test.context.TestContext;
 import org.springframework.test.context.support.DependencyInjectionTestExecutionListener;
 
 import static org.assertj.core.api.Assertions.assertThat;
+import static org.hamcrest.CoreMatchers.is;
 import static org.hamcrest.Matchers.containsString;
 import static org.mockito.BDDMockito.given;
 import static org.mockito.Mockito.mock;
@@ -45,6 +47,9 @@ public class SpringBootDependencyInjectionTestExecutionListenerTests {
 	@Rule
 	public OutputCapture out = new OutputCapture();
 
+	@Rule
+	public ExpectedException thrown = ExpectedException.none();
+
 	private SpringBootDependencyInjectionTestExecutionListener reportListener = new SpringBootDependencyInjectionTestExecutionListener();
 
 	@Test
@@ -74,6 +79,18 @@ public class SpringBootDependencyInjectionTestExecutionListenerTests {
 		this.out.expect(containsString("Negative matches"));
 	}
 
+	@Test
+	public void originalFailureIsThrownWhenReportGenerationFails() throws Exception {
+		TestContext testContext = mock(TestContext.class);
+		IllegalStateException originalFailure = new IllegalStateException();
+		given(testContext.getTestInstance()).willThrow(originalFailure);
+		SpringApplication application = new SpringApplication(Config.class);
+		application.setWebEnvironment(false);
+		given(testContext.getApplicationContext()).willThrow(new RuntimeException());
+		this.thrown.expect(is(originalFailure));
+		this.reportListener.prepareTestInstance(testContext);
+	}
+
 	@Configuration
 	@ImportAutoConfiguration(JacksonAutoConfiguration.class)
 	static class Config {