diff --git a/Essentials/src/com/earth2me/essentials/ISettings.java b/Essentials/src/com/earth2me/essentials/ISettings.java
index 9557960e9..367b4dbae 100644
--- a/Essentials/src/com/earth2me/essentials/ISettings.java
+++ b/Essentials/src/com/earth2me/essentials/ISettings.java
@@ -302,4 +302,8 @@ public interface ISettings extends IConf {
     int getMotdDelay();
 
     boolean isDirectHatAllowed();
-}
\ No newline at end of file
+
+    List<String> getDefaultEnabledConfirmCommands();
+
+    boolean isConfirmCommandEnabledByDefault(String commandName);
+}
diff --git a/Essentials/src/com/earth2me/essentials/Settings.java b/Essentials/src/com/earth2me/essentials/Settings.java
index b85aab2aa..c3ff346c5 100644
--- a/Essentials/src/com/earth2me/essentials/Settings.java
+++ b/Essentials/src/com/earth2me/essentials/Settings.java
@@ -532,6 +532,7 @@ public class Settings implements net.ess3.api.ISettings {
         npcsInBalanceRanking = _isNpcsInBalanceRanking();
         currencyFormat = _getCurrencyFormat();
         unprotectedSigns = _getUnprotectedSign();
+        defaultEnabledConfirmCommands = _getDefaultEnabledConfirmCommands();
     }
 
     private List<Integer> itemSpawnBl = new ArrayList<Integer>();
@@ -1418,4 +1419,24 @@ public class Settings implements net.ess3.api.ISettings {
     public boolean isDirectHatAllowed() {
         return config.getBoolean("allow-direct-hat", true);
     }
-}
\ No newline at end of file
+
+    private List<String> defaultEnabledConfirmCommands;
+
+    private List<String> _getDefaultEnabledConfirmCommands() {
+        List<String> commands = config.getStringList("default-enabled-confirm-commands");
+        for (int i = 0; i < commands.size(); i++) {
+            commands.set(i, commands.get(i).toLowerCase());
+        }
+        return commands;
+    }
+
+    @Override
+    public List<String> getDefaultEnabledConfirmCommands() {
+        return defaultEnabledConfirmCommands;
+    }
+    
+    @Override
+    public boolean isConfirmCommandEnabledByDefault(String commandName) {
+        return getDefaultEnabledConfirmCommands().contains(commandName.toLowerCase());
+    }
+}
diff --git a/Essentials/src/com/earth2me/essentials/UserData.java b/Essentials/src/com/earth2me/essentials/UserData.java
index d38b3ef19..1fe8f5581 100644
--- a/Essentials/src/com/earth2me/essentials/UserData.java
+++ b/Essentials/src/com/earth2me/essentials/UserData.java
@@ -898,14 +898,14 @@ public abstract class UserData extends PlayerExtension implements IConf {
         save();
     }
 
-    private boolean confirmPay = false; // players deny pay confirmation by default
+    private Boolean confirmPay;
 
-    public boolean _getConfirmPay() {
-        return config.getBoolean("confirm-pay", false);
+    private Boolean _getConfirmPay() {
+        return (Boolean) config.get("confirm-pay");
     }
 
     public boolean isPromptingPayConfirm() {
-        return confirmPay;
+        return confirmPay != null ? confirmPay : ess.getSettings().isConfirmCommandEnabledByDefault("pay");
     }
 
     public void setPromptingPayConfirm(boolean prompt) {
@@ -914,14 +914,14 @@ public abstract class UserData extends PlayerExtension implements IConf {
         save();
     }
 
-    private boolean confirmClear = false; // players deny clear confirmation by default
+    private Boolean confirmClear;
 
-    public boolean _getConfirmClear() {
-        return config.getBoolean("confirm-clear", false);
+    private Boolean _getConfirmClear() {
+        return (Boolean) config.get("confirm-clear");
     }
 
     public boolean isPromptingClearConfirm() {
-        return confirmClear;
+        return confirmClear != null ? confirmClear : ess.getSettings().isConfirmCommandEnabledByDefault("clearinventory");
     }
 
     public void setPromptingClearConfirm(boolean prompt) {
diff --git a/Essentials/src/config.yml b/Essentials/src/config.yml
index 22914bc32..656298e7c 100644
--- a/Essentials/src/config.yml
+++ b/Essentials/src/config.yml
@@ -516,6 +516,12 @@ allow-bulk-buy-sell: true
 # This has no effect if the MOTD command or permission are disabled.
 delay-motd: 0
 
+# A list of commands that should have their complementary confirm commands enabled by default.
+# This is empty by default, for the latest list of valid commands see the latest source config.yml.
+default-enabled-confirm-commands:
+#- pay
+#- clearinventory
+
 ############################################################
 # +------------------------------------------------------+ #
 # |                   EssentialsHome                     | #