diff --git a/src/main/java/de/mlessmann/certassist/openssl/OpenSSLCertificateResult.java b/src/main/java/de/mlessmann/certassist/openssl/OpenSSLCertificateResult.java
index bbca3f5..036b9b7 100644
--- a/src/main/java/de/mlessmann/certassist/openssl/OpenSSLCertificateResult.java
+++ b/src/main/java/de/mlessmann/certassist/openssl/OpenSSLCertificateResult.java
@@ -41,12 +41,20 @@ public class OpenSSLCertificateResult implements CertificateUsage {
 
     @Override
     public void close() {
+        cleanupDir(true);
+    }
+
+    private void cleanupDir(boolean retryOnExit) {
+
         try {
             log.info("Cleaning up temporary output directory {}", tmpDir);
             Files.walkFileTree(tmpDir, Set.of(), Integer.MAX_VALUE, new DeleteRecursiveFileVisitor());
             Files.deleteIfExists(tmpDir);
         } catch (IOException e) {
-            log.error("Failed to clean up temporary output directory {}!", tmpDir, e);
+            log.error("Failed to clean up temporary output directory {}! (retry={})", tmpDir, retryOnExit, e);
+            if (retryOnExit) {
+                Runtime.getRuntime().addShutdownHook(new Thread(() -> cleanupDir(false)));
+            }
         }
     }
 }