diff --git a/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/condition/OnBeanCondition.java b/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/condition/OnBeanCondition.java
index 49d0ce2ffb..800f146f95 100644
--- a/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/condition/OnBeanCondition.java
+++ b/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/condition/OnBeanCondition.java
@@ -267,18 +267,32 @@ class OnBeanCondition extends SpringBootCondition implements ConfigurationCondit
 			collect(attributes, "annotation", this.annotations);
 			collect(attributes, "ignored", this.ignoredTypes);
 			collect(attributes, "ignoredType", this.ignoredTypes);
-			if (this.types.isEmpty() && this.names.isEmpty()) {
-				addDeducedBeanType(context, metadata, this.types);
-			}
 			this.strategy = (SearchStrategy) metadata
 					.getAnnotationAttributes(annotationType.getName()).get("search");
-			validate();
+			BeanTypeDeductionException deductionException = null;
+			try {
+				if (this.types.isEmpty() && this.names.isEmpty()) {
+					addDeducedBeanType(context, metadata, this.types);
+				}
+			}
+			catch (BeanTypeDeductionException ex) {
+				deductionException = ex;
+			}
+			validate(deductionException);
 		}
 
-		protected void validate() {
-			Assert.isTrue(hasAtLeastOne(this.types, this.names, this.annotations),
-					annotationName() + " annotations must "
-							+ "specify at least one bean (type, name or annotation)");
+		protected void validate(BeanTypeDeductionException ex) {
+			if (!hasAtLeastOne(this.types, this.names, this.annotations)) {
+				String message = annotationName()
+						+ " did not specify a bean using type, name or annotation";
+				if (ex == null) {
+					throw new IllegalStateException(message);
+				}
+				else {
+					throw new IllegalStateException(message + " and the attempt to deduce"
+							+ " the bean's type failed", ex);
+				}
+			}
 		}
 
 		private boolean hasAtLeastOne(List<?>... lists) {
@@ -337,12 +351,9 @@ class OnBeanCondition extends SpringBootCondition implements ConfigurationCondit
 				});
 			}
 			catch (Throwable ex) {
-				// swallow exception and continue
-				if (logger.isDebugEnabled()) {
-					logger.debug("Unable to deduce bean type for "
-							+ methodMetadata.getDeclaringClassName() + "."
-							+ methodMetadata.getMethodName(), ex);
-				}
+				throw new BeanTypeDeductionException(
+						methodMetadata.getDeclaringClassName(),
+						methodMetadata.getMethodName(), ex);
 			}
 		}
 
@@ -404,11 +415,20 @@ class OnBeanCondition extends SpringBootCondition implements ConfigurationCondit
 		}
 
 		@Override
-		protected void validate() {
+		protected void validate(BeanTypeDeductionException ex) {
 			Assert.isTrue(getTypes().size() == 1, annotationName() + " annotations must "
 					+ "specify only one type (got " + getTypes() + ")");
-
 		}
 	}
 
+	static final class BeanTypeDeductionException extends RuntimeException {
+
+		private BeanTypeDeductionException(String className, String beanMethodName,
+				Throwable cause) {
+			super("Failed to deduce bean type for " + className + "." + beanMethodName,
+					cause);
+		}
+
+	}
+
 }
diff --git a/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/condition/OnBeanConditionTypeDeductionFailureTests.java b/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/condition/OnBeanConditionTypeDeductionFailureTests.java
new file mode 100644
index 0000000000..13d5434a59
--- /dev/null
+++ b/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/condition/OnBeanConditionTypeDeductionFailureTests.java
@@ -0,0 +1,100 @@
+/*
+ * Copyright 2012-2016 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.
+ * You may obtain a copy of the License at
+ *
+ *      http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+package org.springframework.boot.autoconfigure.condition;
+
+import com.fasterxml.jackson.databind.ObjectMapper;
+import org.junit.Test;
+import org.junit.runner.RunWith;
+
+import org.springframework.boot.autoconfigure.condition.OnBeanCondition.BeanTypeDeductionException;
+import org.springframework.boot.testutil.ClassPathExclusions;
+import org.springframework.boot.testutil.FilteredClassPathRunner;
+import org.springframework.context.annotation.AnnotationConfigApplicationContext;
+import org.springframework.context.annotation.Bean;
+import org.springframework.context.annotation.Configuration;
+import org.springframework.context.annotation.Import;
+import org.springframework.context.annotation.ImportSelector;
+import org.springframework.core.type.AnnotationMetadata;
+
+import static org.assertj.core.api.Assertions.assertThat;
+import static org.junit.Assert.fail;
+
+/**
+ * Tests for {@link OnBeanCondition} when deduction of the bean's type fails
+ *
+ * @author Andy Wilkinson
+ */
+@RunWith(FilteredClassPathRunner.class)
+@ClassPathExclusions("jackson-core-*.jar")
+public class OnBeanConditionTypeDeductionFailureTests {
+
+	@Test
+	public void conditionalOnMissingBeanWithDeducedTypeThatIsPartiallyMissingFromClassPath() {
+		try {
+			new AnnotationConfigApplicationContext(ImportingConfiguration.class).close();
+			fail("Context refresh was successful");
+		}
+		catch (Exception ex) {
+			ex.printStackTrace();
+			Throwable beanTypeDeductionException = findBeanTypeDeductionException(ex);
+			assertThat(beanTypeDeductionException)
+					.hasMessage("Failed to deduce bean type for "
+							+ OnMissingBeanConfiguration.class.getName()
+							+ ".objectMapper");
+			assertThat(beanTypeDeductionException)
+					.hasCauseInstanceOf(NoClassDefFoundError.class);
+		}
+	}
+
+	private Throwable findBeanTypeDeductionException(Throwable ex) {
+		Throwable candidate = ex;
+		while (candidate != null) {
+			if (candidate instanceof BeanTypeDeductionException) {
+				return candidate;
+			}
+			candidate = candidate.getCause();
+		}
+		return null;
+	}
+
+	@Configuration
+	@Import(OnMissingBeanImportSelector.class)
+	static class ImportingConfiguration {
+
+	}
+
+	@Configuration
+	static class OnMissingBeanConfiguration {
+
+		@Bean
+		@ConditionalOnMissingBean
+		public ObjectMapper objectMapper() {
+			return new ObjectMapper();
+		}
+
+	}
+
+	static class OnMissingBeanImportSelector implements ImportSelector {
+
+		@Override
+		public String[] selectImports(AnnotationMetadata importingClassMetadata) {
+			return new String[] { OnMissingBeanConfiguration.class.getName() };
+		}
+
+	}
+
+}