diff --git a/spring-boot-project/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/net/protocol/jar/Handler.java b/spring-boot-project/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/net/protocol/jar/Handler.java
index 2778beeccaf..facc6fe6a5d 100644
--- a/spring-boot-project/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/net/protocol/jar/Handler.java
+++ b/spring-boot-project/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/net/protocol/jar/Handler.java
@@ -89,7 +89,7 @@ public class Handler extends URLStreamHandler {
 
 	private String extractContextPath(URL url, String spec, int start) {
 		String contextPath = url.getPath();
-		if (spec.charAt(start) == '/') {
+		if (spec.regionMatches(false, start, "/", 0, 1)) {
 			int indexOfContextPathSeparator = indexOfSeparator(contextPath);
 			if (indexOfContextPathSeparator == -1) {
 				throw new IllegalStateException("malformed context url:%s: no !/".formatted(url));
diff --git a/spring-boot-project/spring-boot-tools/spring-boot-loader/src/test/java/org/springframework/boot/loader/net/protocol/jar/HandlerTests.java b/spring-boot-project/spring-boot-tools/spring-boot-loader/src/test/java/org/springframework/boot/loader/net/protocol/jar/HandlerTests.java
index 8d695721158..6e825480522 100644
--- a/spring-boot-project/spring-boot-tools/spring-boot-loader/src/test/java/org/springframework/boot/loader/net/protocol/jar/HandlerTests.java
+++ b/spring-boot-project/spring-boot-tools/spring-boot-loader/src/test/java/org/springframework/boot/loader/net/protocol/jar/HandlerTests.java
@@ -142,6 +142,15 @@ class HandlerTests {
 		assertThat(url.toExternalForm()).isEqualTo("jar:file:example.jar!/entry.txt#runtime");
 	}
 
+	@Test // gh-38524
+	void parseUrlWhenSpecIsEmpty() throws MalformedURLException {
+		URL url = createJarUrl("nested:gh-38524.jar/!BOOT-INF/classes/!/");
+		String spec = "";
+		this.handler.parseURL(url, spec, 0, 0);
+		assertThat(url.toExternalForm()).isEqualTo("jar:nested:gh-38524.jar/!BOOT-INF/classes/!/");
+
+	}
+
 	@Test
 	void hashCodeGeneratesHashCode() throws MalformedURLException {
 		URL url = createJarUrl("file:example.jar!/entry.txt");