diff --git a/build.gradle b/build.gradle
index 4034d8e..2760119 100644
--- a/build.gradle
+++ b/build.gradle
@@ -30,7 +30,7 @@ runPaper {
 }
 
 runServer {
-    minecraftVersion("1.21.10")
+    minecraftVersion("1.21.11")
     downloadPlugins {
         // for testing from other client versions
         modrinth("ViaVersion", "5.5.1")
diff --git a/src/main/java/de/shiewk/smoderation/paper/SModerationPaper.java b/src/main/java/de/shiewk/smoderation/paper/SModerationPaper.java
index ddfb723..bf9d470 100644
--- a/src/main/java/de/shiewk/smoderation/paper/SModerationPaper.java
+++ b/src/main/java/de/shiewk/smoderation/paper/SModerationPaper.java
@@ -28,7 +28,10 @@ import org.bukkit.plugin.java.JavaPlugin;
 import java.io.File;
 import java.io.InputStream;
 import java.io.InputStreamReader;
+import java.util.ArrayList;
+import java.util.List;
 import java.util.Locale;
+import java.util.Objects;
 
 import static de.shiewk.smoderation.paper.command.VanishCommand.isVanished;
 import static de.shiewk.smoderation.paper.command.VanishCommand.toggleVanish;
@@ -181,14 +184,29 @@ public final class SModerationPaper extends JavaPlugin {
 
             boolean changedSomething = false;
             for (String key : defaultConfig.getKeys(true)) {
-                if (!config.contains(key)) { // There's a new key in the default config
+                if (!config.contains(key)) {
+                    // There's a new key in the default config
                     config.set(key, defaultConfig.get(key));
                     changedSomething = true;
                 }
+
+                List<String> defaultComments = new ArrayList<>(defaultConfig.getComments(key));
+                List<String> comments = new ArrayList<>(config.getComments(key));
+                defaultComments.removeIf(Objects::isNull);
+                comments.removeIf(Objects::isNull);
+
+                if (!defaultComments.equals(comments)) {
+                    // Comments changed
+                    config.setComments(key, defaultConfig.getComments(key));
+                    changedSomething = true;
+                }
             }
 
             // Save the updated configuration file
-            if (changedSomething) saveConfig();
+            if (changedSomething){
+                LOGGER.info("Changing config file to add new options/documentation");
+                saveConfig();
+            }
 
         } catch (Exception e) {
             throw new RuntimeException("Could not update config", e);
diff --git a/src/main/resources/default-config.yml b/src/main/resources/default-config.yml
index 30632fd..821895f 100644
--- a/src/main/resources/default-config.yml
+++ b/src/main/resources/default-config.yml
@@ -1,3 +1,27 @@
+# If enabled, punishments can no longer be issued without providing a reason.
+force-reason: false
+
+# Allows you to toggle specific plugin features.
+features:
+  # Should punishments be tracked and executed?
+  # Note that disabling this will also disable the SMod menu and
+  # /modlogs command since their only use is viewing punishments
+  punishments: true
+  # Should commands for opening the SMod menu be registered?
+  smodmenu: true
+  # Should commands for viewing player inventories be registered?
+  invsee: true
+  # Should commands for viewing player ender chests be registered?
+  enderchestsee: true
+  # Should commands for teleporting to offline players be registered?
+  offlinetp: true
+  # Should commands for viewing other players' messaging commands be registered?
+  socialspy: true
+  # Should players be able to enable vanish mode?
+  vanish: true
+
+# A list of commands which will be captured and broadcast
+# to players which have SocialSpy enabled (/socialspy).
 socialspy-commands:
   - w
   - tell
@@ -9,7 +33,8 @@ socialspy-commands:
   - minecraft:msg
   - minecraft:teammsg
   - minecraft:tm
-force-reason: false
+
+# A list of commands which muted players will not be able to run.
 muted-forbidden-commands:
   - w
   - tell
@@ -22,12 +47,4 @@ muted-forbidden-commands:
   - minecraft:msg
   - minecraft:teammsg
   - minecraft:tm
-  - minecraft:me
-features:
-  punishments: true
-  smodmenu: true
-  invsee: true
-  enderchestsee: true
-  offlinetp: true
-  socialspy: true
-  vanish: true
\ No newline at end of file
+  - minecraft:me
\ No newline at end of file