diff --git a/MMOCore-API/src/main/java/net/Indyuce/mmocore/api/player/PlayerActivity.java b/MMOCore-API/src/main/java/net/Indyuce/mmocore/api/player/PlayerActivity.java
index 65f523c9..5c602d0a 100644
--- a/MMOCore-API/src/main/java/net/Indyuce/mmocore/api/player/PlayerActivity.java
+++ b/MMOCore-API/src/main/java/net/Indyuce/mmocore/api/player/PlayerActivity.java
@@ -23,7 +23,7 @@ public enum PlayerActivity {
 
     CAST_SKILL(() -> MMOCore.plugin.configManager.globalSkillCooldown),
 
-    ;
+    ENTER_CASTING(null);
 
     private final Provider<Long> timeout;
 
diff --git a/MMOCore-API/src/main/java/net/Indyuce/mmocore/api/player/PlayerData.java b/MMOCore-API/src/main/java/net/Indyuce/mmocore/api/player/PlayerData.java
index 48cbc5ef..0616392b 100644
--- a/MMOCore-API/src/main/java/net/Indyuce/mmocore/api/player/PlayerData.java
+++ b/MMOCore-API/src/main/java/net/Indyuce/mmocore/api/player/PlayerData.java
@@ -1007,13 +1007,7 @@ public class PlayerData extends SynchronizedDataHolder implements OfflinePlayerD
     @Deprecated
     public boolean setSkillCasting(@NotNull SkillCastingInstance skillCasting) {
         Validate.isTrue(!isCasting(), "Player already in casting mode");
-        PlayerEnterCastingModeEvent event = new PlayerEnterCastingModeEvent(getPlayer());
-        Bukkit.getPluginManager().callEvent(event);
-        if (event.isCancelled()) return false;
-
-        skillCasting.close();
-        setSkillCasting();
-        return true;
+        return setSkillCasting();
     }
 
     /**
@@ -1025,8 +1019,8 @@ public class PlayerData extends SynchronizedDataHolder implements OfflinePlayerD
         PlayerEnterCastingModeEvent event = new PlayerEnterCastingModeEvent(getPlayer());
         Bukkit.getPluginManager().callEvent(event);
         if (event.isCancelled()) return false;
-
         this.skillCasting = SkillCastingMode.getCurrent().newInstance(this);
+        setLastActivity(PlayerActivity.ENTER_CASTING);
         return true;
     }
 
@@ -1062,10 +1056,26 @@ public class PlayerData extends SynchronizedDataHolder implements OfflinePlayerD
         return true;
     }
 
-    public boolean isCastingTimeoutExpired(){
-        return isCasting() && System.currentTimeMillis() - getLastActivity(PlayerActivity.CAST_SKILL) > (MMOCore.plugin.configManager.castingTimeoutTime * 1000L)  && MMOCore.plugin.configManager.castingTimeoutTime > 0;
+    public boolean isCastingTimeoutExpired() {
+        if (MMOCore.plugin.configManager.castingTimeoutTime <= 0) return false;
+        if (!isCasting()) return false;
+
+        long lastSkillCastTime = getLastActivity(PlayerActivity.CAST_SKILL);
+        long lastEnterCastingTime = getLastActivity(PlayerActivity.ENTER_CASTING);
+
+        // If the player is in casting mode but has not yet cast a skill, use the enter casting time
+        if (lastSkillCastTime == 0L)
+            lastSkillCastTime = lastEnterCastingTime;
+
+        long lastActivityTime = Math.max(lastSkillCastTime, lastEnterCastingTime);
+        long timeSinceLastActivity = System.currentTimeMillis() - lastActivityTime;
+        long castingTimeoutMillis = MMOCore.plugin.configManager.castingTimeoutTime * 1000L;
+
+        return timeSinceLastActivity > castingTimeoutMillis;
     }
 
+
+
     public void displayActionBar(String message) {
         setLastActivity(PlayerActivity.ACTION_BAR_MESSAGE);
         getPlayer().spigot().sendMessage(ChatMessageType.ACTION_BAR, TextComponent.fromLegacyText(message));