diff --git a/src/main/java/xyz/wagyourtail/jvmdg/compile/PathDowngrader.java b/src/main/java/xyz/wagyourtail/jvmdg/compile/PathDowngrader.java
index 0b139e6a..923f1600 100644
--- a/src/main/java/xyz/wagyourtail/jvmdg/compile/PathDowngrader.java
+++ b/src/main/java/xyz/wagyourtail/jvmdg/compile/PathDowngrader.java
@@ -114,7 +114,10 @@ public byte[] apply(String s) {
                                         for (Map.Entry<String, byte[]> entry : outputs.entrySet()) {
                                             String internal = entry.getKey();
                                             Path p = out.resolve(internal + ".class");
-                                            Files.createDirectories(p.getParent());
+                                            Path parent = p.getParent();
+                                            if (parent != null) {
+                                                Files.createDirectories(parent);
+                                            }
                                             Files.write(p, entry.getValue(), StandardOpenOption.CREATE, StandardOpenOption.TRUNCATE_EXISTING);
                                         }
                                     }
diff --git a/src/main/java/xyz/wagyourtail/jvmdg/compile/ZipDowngrader.java b/src/main/java/xyz/wagyourtail/jvmdg/compile/ZipDowngrader.java
index 5f1aac50..aa546f99 100644
--- a/src/main/java/xyz/wagyourtail/jvmdg/compile/ZipDowngrader.java
+++ b/src/main/java/xyz/wagyourtail/jvmdg/compile/ZipDowngrader.java
@@ -46,7 +46,10 @@ public static void downgradeZip(int opcVersion, Path input, Set<URL> classpath,
 
     public static void downgradeZip(final ClassDowngrader downgrader, Path zip, Set<URL> classpath, final Path output) throws IOException {
         try (final FileSystem zipfs = Utils.openZipFileSystem(zip, false)) {
-            Files.createDirectories(output.getParent());
+            Path parent = output.getParent();
+            if (parent != null) {
+                Files.createDirectories(parent);
+            }
             Files.deleteIfExists(output);
             try (final FileSystem outputZipFs = Utils.openZipFileSystem(output, true)) {
                 PathDowngrader.downgradePaths(downgrader, Collections.singletonList(zipfs.getPath("/")), Collections.singletonList(outputZipFs.getPath("/")), classpath);
diff --git a/src/main/java/xyz/wagyourtail/jvmdg/runtime/Bootstrap.java b/src/main/java/xyz/wagyourtail/jvmdg/runtime/Bootstrap.java
index 3cfc2809..e9a2e9fb 100644
--- a/src/main/java/xyz/wagyourtail/jvmdg/runtime/Bootstrap.java
+++ b/src/main/java/xyz/wagyourtail/jvmdg/runtime/Bootstrap.java
@@ -81,7 +81,6 @@ public static void premain(String args, Instrumentation instrumentation) throws
                 downgrade = true;
             }
             if (downgrade) {
-                Files.createDirectories(tmp.getParent());
                 for (File file : tmp.getParent().toFile().listFiles()) {
                     if (file.isDirectory()) continue;
                     if (file.getName().startsWith(name + "-downgraded-" + currentVersionDowngrader.target) && file.getName().endsWith(".jar")) {