diff --git a/paper-api/src/main/java/org/bukkit/plugin/SimplePluginManager.java b/paper-api/src/main/java/org/bukkit/plugin/SimplePluginManager.java
index bcde00a99..47eaabc9d 100644
--- a/paper-api/src/main/java/org/bukkit/plugin/SimplePluginManager.java
+++ b/paper-api/src/main/java/org/bukkit/plugin/SimplePluginManager.java
@@ -236,6 +236,7 @@ public final class SimplePluginManager implements PluginManager {
             plugins.clear();
             lookupNames.clear();
             listeners.clear();
+            fileAssociations.clear();
         }
     }