diff --git a/spring-cloud-contract-wiremock/src/main/java/org/springframework/cloud/contract/wiremock/WireMockConfiguration.java b/spring-cloud-contract-wiremock/src/main/java/org/springframework/cloud/contract/wiremock/WireMockConfiguration.java
index cac6d28b48..93271f7b3e 100644
--- a/spring-cloud-contract-wiremock/src/main/java/org/springframework/cloud/contract/wiremock/WireMockConfiguration.java
+++ b/spring-cloud-contract-wiremock/src/main/java/org/springframework/cloud/contract/wiremock/WireMockConfiguration.java
@@ -113,20 +113,22 @@ public class WireMockConfiguration implements SmartLifecycle {
 	}
 
 	private void registerFiles(com.github.tomakehurst.wiremock.core.WireMockConfiguration factory) throws IOException {
+		List<Resource> resources = new ArrayList<>();
 		for (String files : this.wireMock.getFiles()) {
 			if (StringUtils.hasText(files)) {
 				PathMatchingResourcePatternResolver resolver = new PathMatchingResourcePatternResolver(
 						this.resourceLoader);
-				List<Resource> resources = new ArrayList<>();
 				for (Resource resource : resolver.getResources(files)) {
 					if (resource.exists()) {
 						resources.add(resource);
 					}
 				}
-				ResourcesFileSource fileSource = new ResourcesFileSource(resources.toArray(new Resource[0]));
-				factory.fileSource(fileSource);
 			}
 		}
+		if (!resources.isEmpty()) {
+			ResourcesFileSource fileSource = new ResourcesFileSource(resources.toArray(new Resource[0]));
+			factory.fileSource(fileSource);
+		}
 	}
 
 	@Override
diff --git a/spring-cloud-contract-wiremock/src/main/java/org/springframework/cloud/contract/wiremock/file/ResourcesFileSource.java b/spring-cloud-contract-wiremock/src/main/java/org/springframework/cloud/contract/wiremock/file/ResourcesFileSource.java
index 918a0bcf4a..52b3a709fb 100644
--- a/spring-cloud-contract-wiremock/src/main/java/org/springframework/cloud/contract/wiremock/file/ResourcesFileSource.java
+++ b/spring-cloud-contract-wiremock/src/main/java/org/springframework/cloud/contract/wiremock/file/ResourcesFileSource.java
@@ -34,28 +34,37 @@ import com.github.tomakehurst.wiremock.common.TextFile;
 
 /**
  * @author Dave Syer
- *
+ * @author Pei-Tang Huang
  */
 public class ResourcesFileSource implements FileSource {
 
 	private final FileSource[] sources;
 
-	public ResourcesFileSource(Resource[] resources) {
-		this.sources = new FileSource[resources.length];
+	public ResourcesFileSource(Resource... resources) {
+		this(toSources(resources));
+	}
+
+	private ResourcesFileSource(FileSource... sources) {
+		this.sources = sources;
+	}
+
+	private static FileSource[] toSources(Resource[] resources) {
+		FileSource[] sources = new FileSource[resources.length];
 		for (int i = 0; i < resources.length; i++) {
 			Resource resource = resources[i];
 			if (resource instanceof ClassPathResource) {
 				ClassPathResource classes = (ClassPathResource) resource;
-				this.sources[i] = new ClasspathFileSource(classes.getPath());
+				sources[i] = new ClasspathFileSource(classes.getPath());
 			}
 			else if (resource instanceof FileSystemResource) {
 				FileSystemResource files = (FileSystemResource) resource;
-				this.sources[i] = new SingleRootFileSource(files.getFile());
+				sources[i] = new SingleRootFileSource(files.getFile());
 			}
 			else {
 				throw new IllegalArgumentException("Unsupported resource type for file source: " + resource.getClass());
 			}
 		}
+		return sources;
 	}
 
 	@Override
@@ -94,17 +103,21 @@ public class ResourcesFileSource implements FileSource {
 
 	@Override
 	public FileSource child(String subDirectoryName) {
+		List<FileSource> childSources = new ArrayList<>();
 		for (FileSource resource : this.sources) {
 			try {
 				UrlResource uri = new UrlResource(resource.child(subDirectoryName).getUri());
 				if (uri.createRelative(subDirectoryName).exists()) {
-					return resource.child(subDirectoryName);
+					childSources.add(resource.child(subDirectoryName));
 				}
 			}
 			catch (IOException e) {
 				// Ignore
 			}
 		}
+		if (!childSources.isEmpty()) {
+			return new ResourcesFileSource(childSources.toArray(new FileSource[0]));
+		}
 		return this.sources[0].child(subDirectoryName);
 	}
 
diff --git a/spring-cloud-contract-wiremock/src/test/java/org/springframework/cloud/contract/wiremock/AutoConfigureWireMockStubsAndMultipleFilesApplicationTests.java b/spring-cloud-contract-wiremock/src/test/java/org/springframework/cloud/contract/wiremock/AutoConfigureWireMockStubsAndMultipleFilesApplicationTests.java
index de7e88d1d8..79a0ad2314 100644
--- a/spring-cloud-contract-wiremock/src/test/java/org/springframework/cloud/contract/wiremock/AutoConfigureWireMockStubsAndMultipleFilesApplicationTests.java
+++ b/spring-cloud-contract-wiremock/src/test/java/org/springframework/cloud/contract/wiremock/AutoConfigureWireMockStubsAndMultipleFilesApplicationTests.java
@@ -13,7 +13,7 @@ import org.springframework.test.context.junit4.SpringRunner;
 @RunWith(SpringRunner.class)
 @SpringBootTest(classes=WiremockTestsApplication.class, properties="app.baseUrl=http://localhost:${wiremock.server.port}", webEnvironment=WebEnvironment.NONE)
 @DirtiesContext
-@AutoConfigureWireMock(port=0, files={"classpath:/nonexistent/", "classpath:/root/"}, stubs="file:src/test/resources/io.stubs/mappings")
+@AutoConfigureWireMock(port=0, files={"classpath:/", "classpath:/root/", "classpath:/nonexistent/"}, stubs="file:src/test/resources/io.stubs/mappings")
 public class AutoConfigureWireMockStubsAndMultipleFilesApplicationTests {
 
 	@Autowired