diff --git a/src/main/java/com/github/kristianvld/angeltrophies/CommandHandler.java b/src/main/java/com/github/kristianvld/angeltrophies/CommandHandler.java
index 7b61428..f995537 100644
--- a/src/main/java/com/github/kristianvld/angeltrophies/CommandHandler.java
+++ b/src/main/java/com/github/kristianvld/angeltrophies/CommandHandler.java
@@ -40,9 +40,8 @@ public boolean onCommand(CommandSender sender, Command command, String label, St
             }
             return true;
         } else if (args[0].equalsIgnoreCase("reload")) {
-            if (hasPermission(sender, permissionDeniedMessage)) {
-                Main.getInstance().reload();
-                C.main(sender, "Reloaded {0}.", Main.getInstance().getDescription().getName());
+            if (hasPermission(sender, reloadPermission)) {
+                Main.getInstance().reload(sender);
             }
             return true;
         } else if (!(sender instanceof Player)) {
diff --git a/src/main/java/com/github/kristianvld/angeltrophies/Main.java b/src/main/java/com/github/kristianvld/angeltrophies/Main.java
index be63aff..3987441 100644
--- a/src/main/java/com/github/kristianvld/angeltrophies/Main.java
+++ b/src/main/java/com/github/kristianvld/angeltrophies/Main.java
@@ -6,7 +6,9 @@
 import com.github.kristianvld.angeltrophies.skin.SkinManager;
 import com.github.kristianvld.angeltrophies.trophy.Trophy;
 import com.github.kristianvld.angeltrophies.trophy.TrophyManager;
+import com.github.kristianvld.angeltrophies.util.C;
 import org.bukkit.Material;
+import org.bukkit.command.CommandSender;
 import org.bukkit.configuration.ConfigurationSection;
 import org.bukkit.configuration.file.YamlConfiguration;
 import org.bukkit.event.HandlerList;
@@ -49,12 +51,21 @@ public void onEnable() {
         }
     }
 
-    public void reload() {
-        HandlerList.unregisterAll(skinManager);
-        HandlerList.unregisterAll(trophyManager);
-        getLogger().info("Reloading...");
-        loadManagers();
-        getLogger().info("Done Reloading.");
+    public void reload(CommandSender sender) {
+        try {
+            HandlerList.unregisterAll(skinManager);
+            HandlerList.unregisterAll(trophyManager);
+            getLogger().info("Reloading...");
+            loadManagers();
+            getLogger().info("Done Reloading.");
+            C.main(sender, "Reloaded {0}.", Main.getInstance().getDescription().getName());
+        } catch (Exception e) {
+            getLogger().log(Level.SEVERE, "Error while reloading:", e);
+            getLogger().severe("An error occurred while enabling AngelTrophies, disabling...");
+            C.error(sender, "An error occurred while reload {0}.", Main.getInstance().getDescription().getName());
+            C.error(sender, "Disabling the plugin...");
+            setEnabled(false);
+        }
     }
 
     private void loadManagers() {
diff --git a/src/main/java/com/github/kristianvld/angeltrophies/couch/CouchUtil.java b/src/main/java/com/github/kristianvld/angeltrophies/couch/CouchUtil.java
index 0fa9d33..b11669d 100644
--- a/src/main/java/com/github/kristianvld/angeltrophies/couch/CouchUtil.java
+++ b/src/main/java/com/github/kristianvld/angeltrophies/couch/CouchUtil.java
@@ -18,6 +18,7 @@ public class CouchUtil {
     private static final Map<Pair<String, CouchRole>, Trophy> trophies = new HashMap<>();
 
     public static void buildCache(Collection<Trophy> trophies) {
+        CouchUtil.trophies.clear();
         Set<String> groups = new HashSet<>();
         for (Trophy t : trophies) {
             if (t.getCouchRole() != null) {
diff --git a/src/main/java/com/github/kristianvld/angeltrophies/skin/Skin.java b/src/main/java/com/github/kristianvld/angeltrophies/skin/Skin.java
index da6f67d..aa17168 100644
--- a/src/main/java/com/github/kristianvld/angeltrophies/skin/Skin.java
+++ b/src/main/java/com/github/kristianvld/angeltrophies/skin/Skin.java
@@ -34,7 +34,7 @@ public Skin(Material sourceType, int sourceID, String target, String sticker) {
 
     public Skin(String source, String target, String sticker) {
         if (!OraxenItems.exists(source)) {
-            throw new IllegalArgumentException("Source is not a valid Oraxen item!");
+            throw new IllegalArgumentException("Source is not a valid Oraxen item for Skin '" + sticker + "'. '" + source + "' was not found.");
         }
         ItemStack sourceItem = OraxenItems.getItemById(source).build();
         init(sourceItem.getType(), getModelData(sourceItem), target, sticker);
@@ -46,14 +46,14 @@ private void init(Material sourceType, int sourceID, String target, String stick
         material = sourceType;
         this.sourceID = sourceID;
         if (!OraxenItems.exists(target)) {
-            throw new IllegalArgumentException("Target is not a valid Oraxen item!");
+            throw new IllegalArgumentException("Target is not a valid Oraxen item for the Skin '" + sticker + "', target: '" + target + "'!");
         }
         if (!OraxenItems.exists(sticker)) {
-            throw new IllegalArgumentException("Sticker is not a valid Oraxen item!");
+            throw new IllegalArgumentException("Skin is not a valid Oraxen item for the Skin '" + sticker + "'!");
         }
         ItemStack targetItem = OraxenItems.getItemById(target).build();
         if (targetItem.getType() != sourceType) {
-            throw new IllegalArgumentException("Source and Target needs to be of the same material!");
+            throw new IllegalArgumentException("Source and Target needs to be of the same material for the Skin '" + sticker + "'. Provided target: " + targetItem.getType() + ", provided source: " + sourceType + "!");
         }
         targetID = getModelData(targetItem);
         targetName = target;
diff --git a/src/main/java/com/github/kristianvld/angeltrophies/trophy/Trophy.java b/src/main/java/com/github/kristianvld/angeltrophies/trophy/Trophy.java
index 12c0773..919aea3 100644
--- a/src/main/java/com/github/kristianvld/angeltrophies/trophy/Trophy.java
+++ b/src/main/java/com/github/kristianvld/angeltrophies/trophy/Trophy.java
@@ -57,7 +57,7 @@ public Trophy(String item, boolean floor, boolean floorSmall, double floorOffset
         itemName = item;
         exampleItem = OraxenItems.exists(item) ? OraxenItems.getItemById(item).build() : null;
         if (exampleItem == null || exampleItem.getAmount() <= 0) {
-            throw new IllegalArgumentException("Invalid Oraxen item provided for trophy.");
+            throw new IllegalArgumentException("Invalid Oraxen item provided for trophy '" + item + "'.");
         }
         this.floor = floor;
         this.floorSmall = floorSmall;
@@ -70,7 +70,7 @@ public Trophy(String item, boolean floor, boolean floorSmall, double floorOffset
         this.couchGroup = couchGroup;
         this.couchRole = couchRole;
         if ((couchGroup == null || couchRole == null) && (couchGroup != null || couchRole != null)) {
-            throw new IllegalArgumentException("Both CouchGroup and CouchRole needs to be define, not just one.");
+            throw new IllegalArgumentException("Both CouchGroup and CouchRole needs to be define, not just one for the trophy '" + item + "'.");
         }
     }
 
diff --git a/src/main/java/com/github/kristianvld/angeltrophies/util/C.java b/src/main/java/com/github/kristianvld/angeltrophies/util/C.java
index ac79b32..bcaf3b7 100644
--- a/src/main/java/com/github/kristianvld/angeltrophies/util/C.java
+++ b/src/main/java/com/github/kristianvld/angeltrophies/util/C.java
@@ -28,11 +28,17 @@ public static String prefix(String prefix, String colorBody, String msg, Object.
     }
 
     public static void main(CommandSender receiver, String msg, Object... objs) {
+        if (receiver == null) {
+            return;
+        }
         String message = prefix(prefixMain, colorBodyMain, msg, objs);
         receiver.sendMessage(message);
     }
 
     public static void error(CommandSender receiver, String msg, Object... objs) {
+        if (receiver == null) {
+            return;
+        }
         String message = prefix(prefixError, colorBodyError, msg, objs);
         receiver.sendMessage(message);
     }