diff --git a/Essentials/src/main/java/com/earth2me/essentials/EssentialsPlayerListener.java b/Essentials/src/main/java/com/earth2me/essentials/EssentialsPlayerListener.java
index 8e444c6c7..53f661f80 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/EssentialsPlayerListener.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/EssentialsPlayerListener.java
@@ -260,6 +260,7 @@ public class EssentialsPlayerListener implements Listener, FakeAccessor {
             user.setGodModeEnabled(false);
         }
         if (user.isVanished()) {
+            user.setLeavingHidden(true);
             user.setVanished(false);
         }
         user.setLogoutLocation();
@@ -334,6 +335,7 @@ public class EssentialsPlayerListener implements Listener, FakeAccessor {
                 user.setLastLogin(currentTime);
                 user.setDisplayNick();
                 updateCompass(user);
+                user.setLeavingHidden(false);
 
                 // Check for new username. If they don't want the message, let's just say it's false.
                 final boolean newUsername = ess.getSettings().isCustomNewUsernameMessage() && lastAccountName != null && !lastAccountName.equals(user.getBase().getName());
diff --git a/Essentials/src/main/java/com/earth2me/essentials/IUser.java b/Essentials/src/main/java/com/earth2me/essentials/IUser.java
index b8784add5..f74c7bd03 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/IUser.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/IUser.java
@@ -94,6 +94,15 @@ public interface IUser {
      */
     boolean isHidden();
 
+    /**
+     * Whether the user was hidden before leaving the server.
+     *
+     * @return true if the user was hidden.
+     */
+    boolean isLeavingHidden();
+
+    void setLeavingHidden(boolean leavingHidden);
+
     void setHidden(boolean vanish);
 
     boolean isGodModeEnabled();
diff --git a/Essentials/src/main/java/com/earth2me/essentials/User.java b/Essentials/src/main/java/com/earth2me/essentials/User.java
index 9f13cde5b..96ea5a0e6 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/User.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/User.java
@@ -68,6 +68,7 @@ public class User extends UserData implements Comparable<User>, IMessageRecipien
     // User properties
     private transient boolean vanished;
     private boolean hidden = false;
+    private boolean leavingHidden = false;
     private boolean rightClickJump = false;
     private boolean invSee = false;
     private boolean recipeSee = false;
@@ -681,6 +682,16 @@ public class User extends UserData implements Comparable<User>, IMessageRecipien
         return hidden;
     }
 
+    @Override
+    public boolean isLeavingHidden() {
+        return leavingHidden;
+    }
+
+    @Override
+    public void setLeavingHidden(boolean leavingHidden) {
+        this.leavingHidden = leavingHidden;
+    }
+
     @Override
     public void setHidden(final boolean hidden) {
         this.hidden = hidden;
diff --git a/EssentialsDiscord/src/main/java/net/essentialsx/discord/listeners/BukkitListener.java b/EssentialsDiscord/src/main/java/net/essentialsx/discord/listeners/BukkitListener.java
index 338f9e25b..07d60ba20 100644
--- a/EssentialsDiscord/src/main/java/net/essentialsx/discord/listeners/BukkitListener.java
+++ b/EssentialsDiscord/src/main/java/net/essentialsx/discord/listeners/BukkitListener.java
@@ -120,7 +120,7 @@ public class BukkitListener implements Listener {
 
     @EventHandler(priority = EventPriority.MONITOR, ignoreCancelled = true)
     public void onVanishStatusChange(VanishStatusChangeEvent event) {
-        if (!jda.getSettings().isVanishFakeJoinLeave()) {
+        if (!jda.getSettings().isVanishFakeJoinLeave() || event.getAffected().isLeavingHidden()) {
             return;
         }
         if (event.getValue()) {
@@ -235,7 +235,7 @@ public class BukkitListener implements Listener {
     }
 
     private boolean isVanishHide(final IUser user) {
-        return jda.getSettings().isVanishHideMessages() && user.isHidden();
+        return jda.getSettings().isVanishHideMessages() && (user.isHidden() || user.isLeavingHidden());
     }
 
     private void sendDiscordMessage(final MessageType messageType, final String message) {