diff --git a/src/main/java/solutions/reslate/entertainment/spigotresourcesync/synchronisation/ApacheCommonsIOSynchroniser.java b/src/main/java/solutions/reslate/entertainment/spigotresourcesync/synchronisation/ApacheCommonsIOSynchroniser.java
index 36f0d62..686a007 100644
--- a/src/main/java/solutions/reslate/entertainment/spigotresourcesync/synchronisation/ApacheCommonsIOSynchroniser.java
+++ b/src/main/java/solutions/reslate/entertainment/spigotresourcesync/synchronisation/ApacheCommonsIOSynchroniser.java
@@ -15,6 +15,11 @@ public class ApacheCommonsIOSynchroniser implements Synchroniser {
             source = Path.of(root.getPath(), dest.getPath()).toFile();
         }
 
+        if (source.exists() && dest.exists()) {
+            dest.delete();
+            // Fixes an issue where sometimes, Apache Commons IO will fail to overwrite.
+        }
+
         if (source.isDirectory()) {
             if (dest.isDirectory()) {
                 FileUtils.copyDirectory(source, dest);