diff --git a/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/jar/Handler.java b/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/jar/Handler.java
index d4c1841656..2b7a05670b 100644
--- a/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/jar/Handler.java
+++ b/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/jar/Handler.java
@@ -198,23 +198,23 @@ public class Handler extends URLStreamHandler {
 
 	@Override
 	protected boolean sameFile(URL u1, URL u2) {
-		if (!u1.getProtocol().equals("jar") || u2.getProtocol().equals("jar")) {
-			return super.sameFile(u1, u2);
+		if (!u1.getProtocol().equals("jar") || !u2.getProtocol().equals("jar")) {
+			return false;
 		}
 		int separator1 = u1.getFile().indexOf(SEPARATOR);
-		int separator2 = u1.getFile().indexOf(SEPARATOR);
-		if (separator1 < 0 || separator2 < 0) {
+		int separator2 = u2.getFile().indexOf(SEPARATOR);
+		if (separator1 == -1 || separator2 == -1) {
 			return super.sameFile(u1, u2);
 		}
-		String root1 = u1.getFile().substring(separator1 + SEPARATOR.length());
-		String root2 = u2.getFile().substring(separator2 + SEPARATOR.length());
-		if (!root1.equals(root2)) {
-			return super.sameFile(u1, u2);
+		String nested1 = u1.getFile().substring(separator1 + SEPARATOR.length());
+		String nested2 = u2.getFile().substring(separator2 + SEPARATOR.length());
+		if (!nested1.equals(nested2)) {
+			return false;
 		}
-		String nested1 = u1.getFile().substring(0, separator1);
-		String nested2 = u1.getFile().substring(0, separator2);
+		String root1 = u1.getFile().substring(0, separator1);
+		String root2 = u2.getFile().substring(0, separator2);
 		try {
-			return super.sameFile(new URL(nested1), new URL(nested2));
+			return super.sameFile(new URL(root1), new URL(root2));
 		}
 		catch (MalformedURLException ex) {
 			// Continue
diff --git a/spring-boot-tools/spring-boot-loader/src/test/java/org/springframework/boot/loader/jar/HandlerTests.java b/spring-boot-tools/spring-boot-loader/src/test/java/org/springframework/boot/loader/jar/HandlerTests.java
index 8b5dbe31b1..47862459a3 100644
--- a/spring-boot-tools/spring-boot-loader/src/test/java/org/springframework/boot/loader/jar/HandlerTests.java
+++ b/spring-boot-tools/spring-boot-loader/src/test/java/org/springframework/boot/loader/jar/HandlerTests.java
@@ -89,6 +89,36 @@ public class HandlerTests {
 				.isEqualTo("jar:jar:file:/other.jar!/nested!/entry.txt");
 	}
 
+	@Test
+	public void sameFileReturnsFalseForUrlsWithDifferentProtocols()
+			throws MalformedURLException {
+		assertThat(this.handler.sameFile(new URL("jar:file:foo.jar!/content.txt"),
+				new URL("file:/foo.jar"))).isFalse();
+	}
+
+	@Test
+	public void sameFileReturnsFalseForDifferentFileInSameJar()
+			throws MalformedURLException {
+		assertThat(this.handler.sameFile(
+				new URL("jar:file:foo.jar!/the/path/to/the/first/content.txt"),
+				new URL("jar:file:/foo.jar!/content.txt"))).isFalse();
+	}
+
+	@Test
+	public void sameFileReturnsFalseForSameFileInDifferentJars()
+			throws MalformedURLException {
+		assertThat(this.handler.sameFile(
+				new URL("jar:file:/the/path/to/the/first.jar!/content.txt"),
+				new URL("jar:file:/second.jar!/content.txt"))).isFalse();
+	}
+
+	@Test
+	public void sameFileReturnsTrueForSameFileInSameJar() throws MalformedURLException {
+		assertThat(this.handler.sameFile(
+				new URL("jar:file:/the/path/to/the/first.jar!/content.txt"),
+				new URL("jar:file:/the/path/to/the/first.jar!/content.txt"))).isTrue();
+	}
+
 	private URL createUrl(String file) throws MalformedURLException {
 		return new URL("jar", null, -1, file, this.handler);
 	}