diff --git a/plugin/src/main/java/net/aufdemrand/denizen/Denizen.java b/plugin/src/main/java/net/aufdemrand/denizen/Denizen.java
index 2f6e195445..8db391d2be 100644
--- a/plugin/src/main/java/net/aufdemrand/denizen/Denizen.java
+++ b/plugin/src/main/java/net/aufdemrand/denizen/Denizen.java
@@ -73,6 +73,7 @@
 import net.aufdemrand.denizencore.utilities.debugging.Debuggable;
 import net.aufdemrand.denizencore.utilities.debugging.SlowWarning;
 import net.aufdemrand.denizencore.utilities.debugging.dB.DebugElement;
+import net.aufdemrand.denizencore.utilities.text.ConfigUpdater;
 import net.citizensnpcs.api.CitizensAPI;
 import net.citizensnpcs.api.trait.TraitInfo;
 import org.apache.commons.lang.StringUtils;
@@ -90,8 +91,7 @@
 import org.bukkit.plugin.java.JavaPlugin;
 import org.bukkit.scheduler.BukkitRunnable;
 
-import java.io.File;
-import java.io.IOException;
+import java.io.*;
 import java.net.URLDecoder;
 import java.util.ArrayList;
 import java.util.Arrays;
@@ -266,7 +266,6 @@
 
 public class Denizen extends JavaPlugin implements DenizenImplementation {
 
-    public final static int configVersion = 15;
     public static String versionTag = null;
     private boolean startedSuccessful = false;
 
@@ -486,17 +485,28 @@ public void onEnable() {
         }
 
         try {
-            // Warn if configuration is outdated / too new
-            if (!getConfig().isSet("Config.Version") ||
-                    getConfig().getInt("Config.Version", 0) != configVersion) {
-
-                dB.echoError("Your Denizen config file is from an older version. " +
-                        "Some settings will not be available unless you generate a new one. " +
-                        "This is easily done by stopping the server, deleting the current config.yml file in the Denizen folder " +
-                        "and restarting the server.");
+            // Automatic config file update
+            InputStream properConfig = Denizen.class.getResourceAsStream("/config.yml");
+            String properConfigString = ScriptHelper.convertStreamToString(properConfig);
+            properConfig.close();
+            FileInputStream currentConfig = new FileInputStream(getDataFolder() + "/config.yml");
+            String currentConfigString = ScriptHelper.convertStreamToString(currentConfig);
+            currentConfig.close();
+            String updated = ConfigUpdater.updateConfig(currentConfigString, properConfigString);
+            if (updated != null) {
+                dB.log("Your config file is outdated. Automatically updating it...");
+                FileOutputStream configOutput = new FileOutputStream(getDataFolder() + "/config.yml");
+                OutputStreamWriter writer = new OutputStreamWriter(configOutput);
+                writer.write(updated);
+                writer.close();
+                configOutput.close();
             }
+        }
+        catch (Exception e) {
+            dB.echoError(e);
+        }
 
-            // Create the command script handler for listener
+        try {
             ws_helper = new BukkitWorldScriptHelper();
             ItemScriptHelper is_helper = new ItemScriptHelper();
             InventoryScriptHelper in_helper = new InventoryScriptHelper();
diff --git a/plugin/src/main/resources/config.yml b/plugin/src/main/resources/config.yml
index d7c1e007f2..00e8752881 100644
--- a/plugin/src/main/resources/config.yml
+++ b/plugin/src/main/resources/config.yml
@@ -1,5 +1,6 @@
-# Whether debug information about Denizen should appear in the
-# server console
+# Denizen config.
+
+# Whether debug information about Denizen should appear in the server console
 Debug:
   Show: true
   Ex command help: true
@@ -13,7 +14,7 @@ Debug:
   # This is purely to maintain basic information on things like how many servers run any given version of Denizen.
   # Please do not disable this unless it is throwing errors (Please report any errors you receive as well).
   Stats: true
-  # Whether to force the help command to be the default bukkit help.
+  # Whether to force the help command to be the default bukkit help (required to fix issues with command script help options).
   Override help: true
 
 Scripts:
@@ -157,8 +158,3 @@ Packets:
   # It also enables hiding item script IDs and most likely has no real reason to be disabled.
   # Note that changing this setting requires a full server restart.
   Interception: true
-
-# The version of this configuration file, used to check if your
-# configuration file is outdated or too new
-Config:
-  Version: 15
diff --git a/pom.xml b/pom.xml
index a88b0fbe75..730c3a0128 100644
--- a/pom.xml
+++ b/pom.xml
@@ -12,7 +12,7 @@
         <project.build.sourceEncoding>UTF-8</project.build.sourceEncoding>
         <craftbukkit.version>1.13.2-R0.1-SNAPSHOT</craftbukkit.version>
         <citizens.version>2.0.24-SNAPSHOT</citizens.version>
-        <dcore.version>1.30</dcore.version>
+        <dcore.version>1.40</dcore.version>
         <BUILD_NUMBER>Unknown</BUILD_NUMBER>
         <BUILD_CLASS>CUSTOM</BUILD_CLASS>
         <DENIZEN_VERSION>1.0.3</DENIZEN_VERSION>