diff --git a/worldedit-core/src/main/java/com/fastasyncworldedit/core/configuration/Settings.java b/worldedit-core/src/main/java/com/fastasyncworldedit/core/configuration/Settings.java
index 13e209251..235f92a1d 100644
--- a/worldedit-core/src/main/java/com/fastasyncworldedit/core/configuration/Settings.java
+++ b/worldedit-core/src/main/java/com/fastasyncworldedit/core/configuration/Settings.java
@@ -511,8 +511,7 @@ public class Settings extends Config {
         @Comment("Number of days to keep history on disk before deleting it")
         public int DELETE_AFTER_DAYS = 1;
         @Comment({
-                "If a players clipboard should be removed from memory upon player logout,",
-                " - Will not delete clipboards on disk"
+                "If a player's clipboard should be deleted upon logout"
         })
         public boolean DELETE_ON_LOGOUT = false;
 
diff --git a/worldedit-core/src/main/java/com/sk89q/worldedit/command/ClipboardCommands.java b/worldedit-core/src/main/java/com/sk89q/worldedit/command/ClipboardCommands.java
index 75593f702..d1424f079 100644
--- a/worldedit-core/src/main/java/com/sk89q/worldedit/command/ClipboardCommands.java
+++ b/worldedit-core/src/main/java/com/sk89q/worldedit/command/ClipboardCommands.java
@@ -24,6 +24,7 @@ import com.fastasyncworldedit.core.FaweCache;
 import com.fastasyncworldedit.core.configuration.Caption;
 import com.fastasyncworldedit.core.configuration.Settings;
 import com.fastasyncworldedit.core.event.extent.PasteEvent;
+import com.fastasyncworldedit.core.extent.clipboard.DiskOptimizedClipboard;
 import com.fastasyncworldedit.core.extent.clipboard.MultiClipboardHolder;
 import com.fastasyncworldedit.core.extent.clipboard.ReadOnlyClipboard;
 import com.fastasyncworldedit.core.extent.clipboard.URIClipboardHolder;
@@ -609,6 +610,24 @@ public class ClipboardCommands {
     )
     @CommandPermissions("worldedit.clipboard.clear")
     public void clearClipboard(Actor actor, LocalSession session) throws WorldEditException {
+        //FAWE start - delete DOC
+        ClipboardHolder holder = session.getExistingClipboard();
+        if (holder == null) {
+            return;
+        }
+        for (Clipboard clipboard : holder.getClipboards()) {
+            DiskOptimizedClipboard doc;
+            if (clipboard instanceof DiskOptimizedClipboard) {
+                doc = (DiskOptimizedClipboard) clipboard;
+            } else if (clipboard instanceof BlockArrayClipboard && ((BlockArrayClipboard) clipboard).getParent() instanceof DiskOptimizedClipboard) {
+                doc = (DiskOptimizedClipboard) ((BlockArrayClipboard) clipboard).getParent();
+            } else {
+                continue;
+            }
+            doc.close(); // Ensure closed before deletion
+            doc.getFile().delete();
+        }
+        //FAWE end
         session.setClipboard(null);
         actor.print(Caption.of("worldedit.clearclipboard.cleared"));
     }
diff --git a/worldedit-core/src/main/java/com/sk89q/worldedit/entity/Player.java b/worldedit-core/src/main/java/com/sk89q/worldedit/entity/Player.java
index d72bed418..6380b95bf 100644
--- a/worldedit-core/src/main/java/com/sk89q/worldedit/entity/Player.java
+++ b/worldedit-core/src/main/java/com/sk89q/worldedit/entity/Player.java
@@ -33,6 +33,7 @@ import com.sk89q.worldedit.WorldEdit;
 import com.sk89q.worldedit.WorldEditException;
 import com.sk89q.worldedit.blocks.BaseItemStack;
 import com.sk89q.worldedit.extension.platform.Actor;
+import com.sk89q.worldedit.extent.clipboard.BlockArrayClipboard;
 import com.sk89q.worldedit.extent.clipboard.Clipboard;
 import com.sk89q.worldedit.extent.inventory.BlockBag;
 import com.sk89q.worldedit.function.mask.Mask;
@@ -387,15 +388,32 @@ public interface Player extends Entity, Actor {
     }
 
     /**
-     * Unregister this player, deleting all data stored during the logon session.
+     * Unregister this player, deleting all data stored during the login session.
      */
     default void unregister() {
         cancel(true);
-        if (Settings.IMP.CLIPBOARD.DELETE_ON_LOGOUT || Settings.IMP.CLIPBOARD.USE_DISK) {
-            getSession().setClipboard(null);
+        LocalSession session = getSession();
+        if (Settings.IMP.CLIPBOARD.USE_DISK && Settings.IMP.CLIPBOARD.DELETE_ON_LOGOUT) {
+            ClipboardHolder holder = session.getExistingClipboard();
+            if (holder != null) {
+                for (Clipboard clipboard : holder.getClipboards()) {
+                    DiskOptimizedClipboard doc;
+                    if (clipboard instanceof DiskOptimizedClipboard) {
+                        doc = (DiskOptimizedClipboard) clipboard;
+                    } else if (clipboard instanceof BlockArrayClipboard && ((BlockArrayClipboard) clipboard).getParent() instanceof DiskOptimizedClipboard) {
+                        doc = (DiskOptimizedClipboard) ((BlockArrayClipboard) clipboard).getParent();
+                    } else {
+                        continue;
+                    }
+                    doc.close(); // Ensure closed before deletion
+                    doc.getFile().delete();
+                }
+            }
+        } else if (Settings.IMP.CLIPBOARD.DELETE_ON_LOGOUT || Settings.IMP.CLIPBOARD.USE_DISK) {
+            session.setClipboard(null);
         }
         if (Settings.IMP.HISTORY.DELETE_ON_LOGOUT) {
-            getSession().clearHistory();
+            session.clearHistory();
         }
     }