diff --git a/spring-boot-project/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/net/protocol/nested/NestedLocation.java b/spring-boot-project/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/net/protocol/nested/NestedLocation.java
index 07e304048e6..c350a34fdbf 100644
--- a/spring-boot-project/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/net/protocol/nested/NestedLocation.java
+++ b/spring-boot-project/spring-boot-tools/spring-boot-loader/src/main/java/org/springframework/boot/loader/net/protocol/nested/NestedLocation.java
@@ -102,8 +102,10 @@ public record NestedLocation(Path path, String nestedEntryName) {
 
 	private static NestedLocation create(int index, String location) {
 		String locationPath = location.substring(0, index);
-		if (isWindows() && locationPath.startsWith("/")) {
-			locationPath = locationPath.substring(1, locationPath.length());
+		if (isWindows()) {
+			while (locationPath.startsWith("/")) {
+				locationPath = locationPath.substring(1, locationPath.length());
+			}
 		}
 		String nestedEntryName = location.substring(index + 2);
 		return new NestedLocation((!locationPath.isEmpty()) ? Path.of(locationPath) : null, nestedEntryName);