diff --git a/src/main/java/com/cnaude/purpleirc/PurpleBot.java b/src/main/java/com/cnaude/purpleirc/PurpleBot.java
index cc21dcb..8504e55 100644
--- a/src/main/java/com/cnaude/purpleirc/PurpleBot.java
+++ b/src/main/java/com/cnaude/purpleirc/PurpleBot.java
@@ -55,6 +55,8 @@ import java.util.concurrent.TimeUnit;
 import java.util.concurrent.locks.Lock;
 import java.util.concurrent.locks.ReadWriteLock;
 import java.util.concurrent.locks.ReentrantReadWriteLock;
+import javax.net.SocketFactory;
+import javax.net.ssl.SSLSocketFactory;
 import me.botsko.prism.actionlibs.QueryParameters;
 import me.botsko.prism.events.BlockStateChange;
 import org.bukkit.Achievement;
@@ -69,6 +71,7 @@ import org.pircbotx.Configuration;
 import org.pircbotx.PircBotX;
 import org.pircbotx.User;
 import org.pircbotx.UtilSSLSocketFactory;
+import org.pircbotx.cap.TLSCapHandler;
 import org.pircbotx.exception.IrcException;
 import org.pircbotx.hooks.ListenerAdapter;
 
@@ -87,6 +90,7 @@ public final class PurpleBot {
     private boolean connected;
     public boolean autoConnect;
     public boolean ssl;
+    public boolean tls;
     public boolean trustAllCerts;
     public boolean sendRawMessageOnConnect;
     public boolean showMOTD;
@@ -270,6 +274,9 @@ public final class PurpleBot {
                 socketFactory.trustAllCertificates();
             }
             configBuilder.setSocketFactory(socketFactory);
+            if (tls) {
+                configBuilder.addCapHandler(new TLSCapHandler(socketFactory, true));
+            }
         }
         if (charSet.isEmpty()) {
             if (!reload) {
@@ -630,6 +637,7 @@ public final class PurpleBot {
             config.load(file);
             autoConnect = config.getBoolean("autoconnect", true);
             ssl = config.getBoolean("ssl", false);
+            tls = config.getBoolean("tls", false);
             trustAllCerts = config.getBoolean("trust-all-certs", false);
             sendRawMessageOnConnect = config.getBoolean("raw-message-on-connect", false);
             rawMessage = config.getString("raw-message", "");
@@ -668,6 +676,7 @@ public final class PurpleBot {
             plugin.logDebug("Channel Auto Join Delay => " + channelAutoJoinDelay);
             plugin.logDebug(("Bind => ") + bindAddress);
             plugin.logDebug("SSL => " + ssl);
+            plugin.logDebug("TLS => " + tls);
             plugin.logDebug("Trust All Certs => " + trustAllCerts);
             plugin.logDebug("Port => " + botServerPort);
             plugin.logDebug("Command Prefix => " + commandPrefix);
@@ -693,7 +702,7 @@ public final class PurpleBot {
             for (String s : config.getStringList("custom-prefixes")) {
                 String pair[] = s.split(" ", 2);
                 if (pair.length > 0) {
-                    userPrefixes.put(pair[0], ChatColor.translateAlternateColorCodes('&', pair[1]));  
+                    userPrefixes.put(pair[0], ChatColor.translateAlternateColorCodes('&', pair[1]));
                 }
             }
             for (String key : userPrefixes.keySet()) {
@@ -941,7 +950,7 @@ public final class PurpleBot {
                     connectMessage = "Connecting to " + botServer + ":"
                             + botServerPort + ": [Nick: " + botNick
                             + "] [SSL: " + ssl + "]" + " [TrustAllCerts: "
-                            + trustAllCerts + "]";
+                            + trustAllCerts + "] [TLS: " + tls + "]";
                 }
             }
         } catch (IOException | InvalidConfigurationException ex) {
diff --git a/src/main/java/com/cnaude/purpleirc/PurpleIRC.java b/src/main/java/com/cnaude/purpleirc/PurpleIRC.java
index 5f93fdd..def5352 100644
--- a/src/main/java/com/cnaude/purpleirc/PurpleIRC.java
+++ b/src/main/java/com/cnaude/purpleirc/PurpleIRC.java
@@ -87,6 +87,8 @@ import org.bukkit.command.CommandSender;
 import org.bukkit.configuration.InvalidConfigurationException;
 import org.bukkit.configuration.file.YamlConfiguration;
 import org.bukkit.entity.Player;
+import org.bukkit.permissions.PermissionAttachment;
+import org.bukkit.permissions.PermissionAttachmentInfo;
 import org.bukkit.plugin.Plugin;
 import org.bukkit.plugin.java.JavaPlugin;
 import org.pircbotx.IdentServer;
@@ -412,7 +414,7 @@ public class PurpleIRC extends JavaPlugin {
         botWatcher = new BotWatcher(this);
         ircMessageHandler = new IRCMessageHandler(this);
         commandQueue = new CommandQueueWatcher(this);
-        updateChecker = new UpdateChecker(this);
+        updateChecker = new UpdateChecker(this);        
     }
 
     /**
@@ -968,6 +970,7 @@ public class PurpleIRC extends JavaPlugin {
         try {
             if (vaultHelpers != null) {
                 if (vaultHelpers.permission != null && vaultHelpers.permission != null) {
+                    logDebug("getPlayerGroup: " + player.getName());
                     groupName = vaultHelpers.permission.getPrimaryGroup(player);
                 }
             }
@@ -1006,6 +1009,7 @@ public class PurpleIRC extends JavaPlugin {
                 if (vaultHelpers.permission != null && vaultHelpers.permission != null) {
                     OfflinePlayer offlinePlayer = getServer().getOfflinePlayer(uuid);
                     if (offlinePlayer != null) {
+                        logDebug("getPlayerGroup: " + worldName + " " + player);
                         groupName = vaultHelpers.permission.getPrimaryGroup(worldName, offlinePlayer);
                     }
                 }
@@ -1051,6 +1055,7 @@ public class PurpleIRC extends JavaPlugin {
                 if (vaultHelpers.chat != null) {
                     OfflinePlayer offlinePlayer = getServer().getOfflinePlayer(uuid);
                     if (offlinePlayer != null) {
+                        logDebug("getPlayerPrefix: " + worldName + " " + player);
                         prefix = vaultHelpers.chat.getPlayerPrefix(worldName, offlinePlayer);
                     }
                 }
@@ -1096,6 +1101,7 @@ public class PurpleIRC extends JavaPlugin {
                 if (vaultHelpers.chat != null) {
                     OfflinePlayer offlinePlayer = getServer().getOfflinePlayer(uuid);
                     if (offlinePlayer != null) {
+                        logDebug("getPlayerSuffix: " + worldName + " " + offlinePlayer.getName());
                         suffix = vaultHelpers.chat.getPlayerSuffix(worldName, offlinePlayer);
                     }
                 }
diff --git a/src/main/java/com/cnaude/purpleirc/Utilities/CaseInsensitiveMap.java b/src/main/java/com/cnaude/purpleirc/Utilities/CaseInsensitiveMap.java
index 0e79e00..40d4df3 100644
--- a/src/main/java/com/cnaude/purpleirc/Utilities/CaseInsensitiveMap.java
+++ b/src/main/java/com/cnaude/purpleirc/Utilities/CaseInsensitiveMap.java
@@ -34,7 +34,7 @@ import java.util.concurrent.ConcurrentHashMap;
  */
 public class CaseInsensitiveMap<V> extends AbstractMap<String, V> {
 
-    private final Map<CaseInsensitiveKey, V> map = new ConcurrentHashMap<CaseInsensitiveKey, V>();
+    private final Map<CaseInsensitiveKey, V> map = new ConcurrentHashMap<>();
 
     private static final class KeySet extends AbstractSet<String> {
 
@@ -201,7 +201,7 @@ public class CaseInsensitiveMap<V> extends AbstractMap<String, V> {
              */
             @Override
             public Entry<String, V> next() {
-                return new MapEntry<V>(this.iterator.next());
+                return new MapEntry<>(this.iterator.next());
             }
 
             /**
@@ -265,7 +265,7 @@ public class CaseInsensitiveMap<V> extends AbstractMap<String, V> {
          */
         @Override
         public Iterator<Entry<String, V>> iterator() {
-            return new EntrySetIterator<V>(this.entrySet.iterator());
+            return new EntrySetIterator<>(this.entrySet.iterator());
         }
 
         /**
@@ -397,7 +397,7 @@ public class CaseInsensitiveMap<V> extends AbstractMap<String, V> {
      */
     @Override
     public Set<Entry<String, V>> entrySet() {
-        return new EntrySet<V>(this.map.entrySet(), this);
+        return new EntrySet<>(this.map.entrySet(), this);
     }
 
     /**
diff --git a/src/main/resources/SampleBot.yml b/src/main/resources/SampleBot.yml
index 422a99c..568b785 100644
--- a/src/main/resources/SampleBot.yml
+++ b/src/main/resources/SampleBot.yml
@@ -19,6 +19,8 @@ server: irc.excample.com
 port: 6667
 # Attempt ssl connection to IRC server
 ssl: false
+# Enable TLS support
+tls: false
 # Trust all SSL certs
 trust-all-certs: false
 # Bind address