diff --git a/eco-core/core-plugin/src/main/kotlin/com/willfp/ecoshop/EcoShopPlugin.kt b/eco-core/core-plugin/src/main/kotlin/com/willfp/ecoshop/EcoShopPlugin.kt
index 63abcce..bab6721 100644
--- a/eco-core/core-plugin/src/main/kotlin/com/willfp/ecoshop/EcoShopPlugin.kt
+++ b/eco-core/core-plugin/src/main/kotlin/com/willfp/ecoshop/EcoShopPlugin.kt
@@ -10,6 +10,8 @@ import com.willfp.ecoshop.commands.CommandEcoShop
 import com.willfp.ecoshop.commands.CommandSell
 import com.willfp.ecoshop.config.UsermadeConfig
 import com.willfp.ecoshop.integration.EcoShopAdapter
+import com.willfp.ecoshop.shop.Shops
+import com.willfp.ecoshop.shop.gui.SellGUI
 import org.bukkit.event.Listener
 import java.io.File
 import java.util.zip.ZipFile
@@ -24,6 +26,13 @@ class EcoShopPlugin : EcoPlugin() {
     override fun handleEnable() {
         copyConfigs("categories")
         copyConfigs("shops")
+        Shops.update(this)
+        SellGUI.update(this)
+    }
+
+    override fun handleReload() {
+        Shops.update(this)
+        SellGUI.update(this)
     }
 
     private fun copyConfigs(directory: String) {
diff --git a/eco-core/core-plugin/src/main/kotlin/com/willfp/ecoshop/shop/ShopItem.kt b/eco-core/core-plugin/src/main/kotlin/com/willfp/ecoshop/shop/ShopItem.kt
index b779d39..23f9880 100644
--- a/eco-core/core-plugin/src/main/kotlin/com/willfp/ecoshop/shop/ShopItem.kt
+++ b/eco-core/core-plugin/src/main/kotlin/com/willfp/ecoshop/shop/ShopItem.kt
@@ -41,7 +41,13 @@ class ShopItem(
 ) {
     val id = config.getString("id")
 
-    val commands = config.getStringsOrNull("command")
+    val commands = config.getStrings("command") + config.getStrings("commands")
+
+    val sellCommand = config.getStringsOrNull("sell.sell-commands")
+
+    val sellItemMessage = config.getStringsOrNull("sell.sell-message")
+
+    val buyItemMessage = config.getStringsOrNull("buy.buy-message")
 
     val item = if (config.has("item")) Items.lookup(config.getString("item")) else null
 
@@ -262,11 +268,18 @@ class ShopItem(
             queue.push()
         }
 
-        if (commands != null) {
-            for (command in commands) {
-                Bukkit.dispatchCommand(
-                    Bukkit.getConsoleSender(),
-                    command.replace("%player%", player.name)
+        for (command in commands) {
+            Bukkit.dispatchCommand(
+                Bukkit.getConsoleSender(),
+                command.replace("%player%", player.name)
+                    .replace("%amount%", amount.toString())
+            )
+        }
+        if (buyItemMessage != null) {
+            for (message in buyItemMessage) {
+                player.sendMessage(
+                    message.formatEco()
+                        .replace("%player%", player.name)
                         .replace("%amount%", amount.toString())
                 )
             }
@@ -354,8 +367,27 @@ class ShopItem(
 
         shop?.sellSound?.playTo(player)
 
+        if (sellCommand != null) {
+            for (command in sellCommand) {
+                Bukkit.dispatchCommand(
+                    Bukkit.getConsoleSender(),
+                    command.replace("%player%", player.name)
+                        .replace("%amount%", amountSold.toString())
+                )
+            }
+        }
+        if (sellItemMessage != null) {
+            for (message in sellItemMessage) {
+                player.sendMessage(
+                    message.formatEco()
+                        .replace("%player%", player.name)
+                        .replace("%amount%", amountSold.toString())
+                )
+            }
+        }
+
         return amountSold
-    }
+        }
 
     fun getAmountInPlayerInventory(player: Player): Int {
         if (item == null) {
diff --git a/eco-core/core-plugin/src/main/kotlin/com/willfp/ecoshop/shop/Shops.kt b/eco-core/core-plugin/src/main/kotlin/com/willfp/ecoshop/shop/Shops.kt
index a51ceb6..e8f8b32 100644
--- a/eco-core/core-plugin/src/main/kotlin/com/willfp/ecoshop/shop/Shops.kt
+++ b/eco-core/core-plugin/src/main/kotlin/com/willfp/ecoshop/shop/Shops.kt
@@ -30,7 +30,6 @@ object Shops {
         return ImmutableList.copyOf(BY_ID.values)
     }
 
-    @ConfigUpdater
     @JvmStatic
     fun update(plugin: EcoShopPlugin) {
         ShopCategories.update(plugin)
diff --git a/eco-core/core-plugin/src/main/kotlin/com/willfp/ecoshop/shop/gui/SellGUI.kt b/eco-core/core-plugin/src/main/kotlin/com/willfp/ecoshop/shop/gui/SellGUI.kt
index 25c23f2..4aa2f50 100644
--- a/eco-core/core-plugin/src/main/kotlin/com/willfp/ecoshop/shop/gui/SellGUI.kt
+++ b/eco-core/core-plugin/src/main/kotlin/com/willfp/ecoshop/shop/gui/SellGUI.kt
@@ -18,7 +18,6 @@ object SellGUI {
     private lateinit var menu: Menu
 
     @JvmStatic
-    @ConfigUpdater
     fun update(plugin: EcoShopPlugin) {
         val rows = plugin.configYml.getInt("sell-gui.rows")
 
diff --git a/eco-core/core-plugin/src/main/resources/categories/_example.yml b/eco-core/core-plugin/src/main/resources/categories/_example.yml
index 508029a..098bcd8 100644
--- a/eco-core/core-plugin/src/main/resources/categories/_example.yml
+++ b/eco-core/core-plugin/src/main/resources/categories/_example.yml
@@ -74,6 +74,9 @@ items:
       amount: 8 # (Optional) The quick buy / default buy amount. Defaults to 1 if not specified.
       max-at-once: 16 # (Optional) The maximum amount that can be bought at once. Defaults to infinity if not specified.
 
+      buy-message: # (Optional) Enter messages to send to the player when the player buys this specific items. It will still send the 'bought-item/bought-multiple' from lang.yml
+        - "&6Thanks for buying this specific item"
+
     # Options for selling the item, see here:
     # https://plugins.auxilor.io/all-plugins/prices
     sell:
@@ -83,6 +86,10 @@ items:
 
       require: "%player_rank% > 1" # (Optional) This expression must hold true to be allowed to sell this item.
 
+      sell-command: # (Optional) Enter commands that should be executed when a player sells items. You can use %player% and %amount% placeholders
+        - "give %player% stone %amount%"
+      sell-message: # (Optional) Enter messages to send to the player when the player sells this specific items. It will still send the 'sold-item/sold-multiple' from lang.yml
+        - "&6Thanks for selling this specific item"
     gui:
       column: 4 # How far left to right (1-9).
       row: 3 # How far up or down (1-6).