diff --git a/EssentialsDiscord/src/main/java/net/essentialsx/discord/JDADiscordService.java b/EssentialsDiscord/src/main/java/net/essentialsx/discord/JDADiscordService.java
index 129b64985..a1030442c 100644
--- a/EssentialsDiscord/src/main/java/net/essentialsx/discord/JDADiscordService.java
+++ b/EssentialsDiscord/src/main/java/net/essentialsx/discord/JDADiscordService.java
@@ -333,7 +333,7 @@ public class JDADiscordService implements DiscordService, IEssentialsModule {
                 if (current != null) {
                     current.close();
                 }
-                channelIdToWebhook.remove(channel.getId());
+                channelIdToWebhook.remove(channel.getId()).close();
                 continue;
             }
             typeToChannelId.put(type, channel.getId());
@@ -430,6 +430,10 @@ public class JDADiscordService implements DiscordService, IEssentialsModule {
 
             shutdownConsoleRelay(true);
 
+            for (WebhookClient webhook : channelIdToWebhook.values()) {
+                webhook.close();
+            }
+
             // Unregister leftover jda listeners
             for (Object obj : jda.getRegisteredListeners()) {
                 if (!(obj instanceof EventListener)) { // Yeah bro I wish I knew too :/