diff --git a/runelite-client/src/main/java/net/runelite/client/RuneLite.java b/runelite-client/src/main/java/net/runelite/client/RuneLite.java
index c25d767db6..b507f796d5 100644
--- a/runelite-client/src/main/java/net/runelite/client/RuneLite.java
+++ b/runelite-client/src/main/java/net/runelite/client/RuneLite.java
@@ -55,6 +55,8 @@ import net.runelite.client.game.ItemManager;
 import net.runelite.client.game.LootManager;
 import net.runelite.client.game.chatbox.ChatboxPanelManager;
 import net.runelite.client.menus.MenuManager;
+import net.runelite.client.plugins.Plugin;
+import net.runelite.client.plugins.PluginInstantiationException;
 import net.runelite.client.plugins.PluginManager;
 import net.runelite.client.rs.ClientUpdateCheckMode;
 import net.runelite.client.ui.ClientUI;
@@ -294,6 +296,18 @@ public class RuneLite
 		configManager.sendConfig();
 		clientSessionManager.shutdown();
 		discordService.close();
+
+		for (final Plugin plugin : pluginManager.getPlugins())
+		{
+			try
+			{
+				pluginManager.stopPlugin(plugin);
+			}
+			catch (PluginInstantiationException e)
+			{
+				log.warn("Failed to gracefully close plugin", e);
+			}
+		}
 	}
 
 	@VisibleForTesting
diff --git a/runelite-client/src/main/java/net/runelite/client/util/SwingUtil.java b/runelite-client/src/main/java/net/runelite/client/util/SwingUtil.java
index 39fc738f1f..5080db032a 100644
--- a/runelite-client/src/main/java/net/runelite/client/util/SwingUtil.java
+++ b/runelite-client/src/main/java/net/runelite/client/util/SwingUtil.java
@@ -216,10 +216,16 @@ public class SwingUtil
 
 				if (result == JOptionPane.OK_OPTION)
 				{
-					callback.run();
-					System.exit(0);
+					frame.dispose();
 				}
 			}
+
+			@Override
+			public void windowClosed(WindowEvent event)
+			{
+				callback.run();
+				System.exit(0);
+			}
 		});
 	}