diff --git a/spring-boot-cli/src/main/java/org/springframework/boot/cli/command/jar/JarCommand.java b/spring-boot-cli/src/main/java/org/springframework/boot/cli/command/jar/JarCommand.java
index 51f3be65f80..e6748ac4cb4 100644
--- a/spring-boot-cli/src/main/java/org/springframework/boot/cli/command/jar/JarCommand.java
+++ b/spring-boot-cli/src/main/java/org/springframework/boot/cli/command/jar/JarCommand.java
@@ -155,9 +155,11 @@ public class JarCommand extends OptionParsingCommand {
 					options.valuesOf(this.excludeOption));
 			List<File> roots = new ArrayList<File>();
 			for (URL classpathEntry : classpath) {
-				roots.add(new File(URI.create(classpathEntry.toString())));
+				File file = new File(URI.create(classpathEntry.toString()));
+				roots.add(file);
 			}
-			return matcher.find(roots);
+			List<MatchedResource> found = matcher.find(roots);
+			return found;
 		}
 
 		private void writeJar(File file, Class<?>[] compiledClasses,
diff --git a/spring-boot-cli/src/main/java/org/springframework/boot/cli/command/jar/ResourceMatcher.java b/spring-boot-cli/src/main/java/org/springframework/boot/cli/command/jar/ResourceMatcher.java
index 7523b11b40d..403cf2ebd8b 100644
--- a/spring-boot-cli/src/main/java/org/springframework/boot/cli/command/jar/ResourceMatcher.java
+++ b/spring-boot-cli/src/main/java/org/springframework/boot/cli/command/jar/ResourceMatcher.java
@@ -147,7 +147,7 @@ class ResourceMatcher {
 		private MatchedResource(File file) {
 			this.name = file.getName();
 			this.file = file;
-			this.root = false;
+			this.root = this.name.endsWith(".jar");
 		}
 
 		private MatchedResource(File rootFolder, File file) {
diff --git a/spring-boot-cli/src/test/java/org/springframework/boot/cli/command/jar/ResourceMatcherTests.java b/spring-boot-cli/src/test/java/org/springframework/boot/cli/command/jar/ResourceMatcherTests.java
index 288e48a594a..8a242addf5d 100644
--- a/spring-boot-cli/src/test/java/org/springframework/boot/cli/command/jar/ResourceMatcherTests.java
+++ b/spring-boot-cli/src/test/java/org/springframework/boot/cli/command/jar/ResourceMatcherTests.java
@@ -22,10 +22,15 @@ import java.util.ArrayList;
 import java.util.Arrays;
 import java.util.List;
 
+import org.hamcrest.Description;
+import org.hamcrest.TypeSafeMatcher;
 import org.junit.Test;
 import org.springframework.boot.cli.command.jar.ResourceMatcher.MatchedResource;
 
+import static org.hamcrest.Matchers.hasItem;
+import static org.hamcrest.Matchers.not;
 import static org.junit.Assert.assertEquals;
+import static org.junit.Assert.assertThat;
 import static org.junit.Assert.assertTrue;
 
 /**
@@ -45,6 +50,27 @@ public class ResourceMatcherTests {
 		assertEquals(0, matchedResources.size());
 	}
 
+	@Test
+	public void excludedWins() throws Exception {
+		ResourceMatcher resourceMatcher = new ResourceMatcher(Arrays.asList("*"),
+				Arrays.asList("**/*.jar"));
+		List<MatchedResource> found = resourceMatcher.find(Arrays.asList(new File(
+				"src/test/resources")));
+		assertThat(found, not(hasItem(new FooJarMatcher(MatchedResource.class))));
+	}
+
+	@Test
+	public void jarFileAlwaysMatches() throws Exception {
+		ResourceMatcher resourceMatcher = new ResourceMatcher(Arrays.asList("*"),
+				Arrays.asList("**/*.jar"));
+		List<MatchedResource> found = resourceMatcher.find(Arrays.asList(new File(
+				"src/test/resources/templates"), new File("src/test/resources/foo.jar")));
+		FooJarMatcher matcher = new FooJarMatcher(MatchedResource.class);
+		assertThat(found, hasItem(matcher));
+		// A jar file is always treated as a dependency (stick it in /lib)
+		assertTrue(matcher.getMatched().isRoot());
+	}
+
 	@Test
 	public void resourceMatching() throws IOException {
 		List<MatchedResource> matchedResources = this.resourceMatcher.find(Arrays.asList(
@@ -61,4 +87,32 @@ public class ResourceMatcherTests {
 		assertTrue(paths.containsAll(Arrays.asList("alpha/nested/fileA", "bravo/fileC",
 				"fileD", "bravo/fileE", "fileF", "three")));
 	}
+
+	private final class FooJarMatcher extends TypeSafeMatcher<MatchedResource> {
+
+		private MatchedResource matched;
+
+		public MatchedResource getMatched() {
+			return this.matched;
+		}
+
+		private FooJarMatcher(Class<?> expectedType) {
+			super(expectedType);
+		}
+
+		@Override
+		public void describeTo(Description description) {
+			description.appendText("foo.jar");
+		}
+
+		@Override
+		protected boolean matchesSafely(MatchedResource item) {
+			boolean matches = item.getFile().getName().equals("foo.jar");
+			if (matches) {
+				this.matched = item;
+			}
+			return matches;
+		}
+	}
+
 }