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 90d186d325..2a616a2a95 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
@@ -1,5 +1,5 @@
 /*
- * Copyright 2012-2016 the original author or authors.
+ * Copyright 2012-2017 the original author or authors.
  *
  * Licensed under the Apache License, Version 2.0 (the "License");
  * you may not use this file except in compliance with the License.
@@ -44,20 +44,25 @@ public class SpringBootDependencyInjectionTestExecutionListener
 			super.prepareTestInstance(testContext);
 		}
 		catch (Exception ex) {
-			try {
-				ApplicationContext context = testContext.getApplicationContext();
-				if (context instanceof ConfigurableApplicationContext) {
-					ConditionEvaluationReport report = ConditionEvaluationReport
-							.get(((ConfigurableApplicationContext) context).getBeanFactory());
-					System.err.println(new ConditionEvaluationReportMessage(report));
-				}
-			}
-			catch (Exception ignore) {
-			}
+			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));
+			}
+		}
+		catch (Exception ex) {
+			// Allow original failure to be reported
+		}
+	}
+
 	static class PostProcessor implements DefaultTestExecutionListenersPostProcessor {
 
 		@Override
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 db0df23ced..408e58718d 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.autoconfigure.ImportAutoConfiguration;
@@ -30,6 +31,7 @@ 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;
@@ -44,6 +46,9 @@ public class SpringBootDependencyInjectionTestExecutionListenerTests {
 	@Rule
 	public OutputCapture out = new OutputCapture();
 
+	@Rule
+	public ExpectedException thrown = ExpectedException.none();
+
 	private SpringBootDependencyInjectionTestExecutionListener reportListener = new SpringBootDependencyInjectionTestExecutionListener();
 
 	@Test
@@ -73,6 +78,18 @@ 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 {