diff --git a/src/main/java/org/simplemc/simpleannounce/SimpleAnnounce.java b/src/main/java/org/simplemc/simpleannounce/SimpleAnnounce.java
index da737ef..db716f5 100755
--- a/src/main/java/org/simplemc/simpleannounce/SimpleAnnounce.java
+++ b/src/main/java/org/simplemc/simpleannounce/SimpleAnnounce.java
@@ -1,5 +1,6 @@
 package org.simplemc.simpleannounce;
 
+import java.util.Arrays;
 import java.util.LinkedList;
 import java.util.List;
 import java.util.Set;
@@ -14,7 +15,7 @@
 import org.bukkit.plugin.java.JavaPlugin;
 
 import org.simplemc.simpleannounce.message.Message;
-import org.simplemc.simpleannounce.message.RepeatingMessage;
+import org.simplemc.simpleannounce.message.MessageGroup;
 import org.simplemc.simpleannounce.message.sender.BossBarSender;
 import org.simplemc.simpleannounce.message.sender.ChatMessageSender;
 import org.simplemc.simpleannounce.message.sender.MessageSender;
@@ -108,17 +109,33 @@ private void validateConfig()
         // messages
         if (!getConfig().contains("messages"))
         {
-            getConfig().set("messages.default1.message", "This is an automatically generated repeating message!");
-            getConfig().set("messages.default1.delay", 15);
-            getConfig().set("messages.default1.repeat", 60);
-            getConfig().set("messages.default2.message", "This is another automatically generated repeating message for people with build permission!");
-            getConfig().set("messages.default2.delay", 30);
-            getConfig().set("messages.default2.repeat", 60);
-            List<String> df2Includes = new LinkedList<>();
-            df2Includes.add("permissions.build");
-            getConfig().set("messages.default2.includesperms", df2Includes);
-            getConfig().set("messages.default3.message", "This is an automatically generated one-time message!");
-            getConfig().set("messages.default3.delay", 45);
+            // example repeating message
+            getConfig().set("messages.repeating-example.message", "This is an automatically generated repeating message!");
+            getConfig().set("messages.repeating-example.delay", 15);
+            getConfig().set("messages.repeating-example.repeat", 60);
+
+            // example repeating message with perms
+            getConfig().set("messages.permissions-example.message", "This is another automatically generated repeating message for people with build permission!");
+            getConfig().set("messages.permissions-example.delay", 30);
+            getConfig().set("messages.permissions-example.repeat", 60);
+            getConfig().set("messages.permissions-example.includesperms", Arrays.asList(new String[]{"permissions.build"}));
+
+            // example one time message
+            getConfig().set("messages.one-time-example.message", "This is an automatically generated one-time message!");
+            getConfig().set("messages.one-time-example.delay", 45);
+
+            // example message group with boss bar sender
+            getConfig().set("messages.message-group-example.messages",
+                    Arrays.asList(new String[]
+                            {
+                                    "This is an automatically generated sequential message group (1 of 3)!",
+                                    "This is an automatically generated sequential message group (2 of 3)!",
+                                    "This is an automatically generated sequential message group (3 of 3)!"
+                            }));
+            getConfig().set("messages.message-group-example.delay", 30);
+            getConfig().set("messages.message-group-example.repeat", 30);
+            getConfig().set("messages.message-group-example.sender", "bossbar");
+            getConfig().set("messages.message-group-example.random-order", false);
             updated = true;
         }
 
@@ -138,7 +155,8 @@ private void validateConfig()
                     "-------------------------\n" +
                     "\n" +
                     "<message label>(String, must be unique):\n" +
-                    "    message(String, required): <Message to send>\n" +
+                    "    message(String, required) OR messages(String list, see sample config): <Message to send>\n" +
+                    "    random-order(boolean, optional): <if list of messages should be sent in random order>\n" +
                     "    sender(String, optional): <Message Sender(chat or boss, default: chat)>\n" +
                     "    bar(section, optional):\n" +
                     "        hold(int, optional): <Time in sections for bar to be displayed on announce>\n" +
@@ -179,10 +197,6 @@ private void addMessages(Set<String> nodes, ConfigurationSection section)
         ConfigurationSection currentSec; // current message config section
         Message current; // current message we're working with
         MessageSender sender; // message sender
-        String label; // unique message label
-        String message; // actual message text
-        int delay; // delay of message
-        int repeat; // repeat timer of message
 
         // go through all message nodes and get data from it
         for (String messageNode : nodes)
@@ -190,60 +204,109 @@ private void addMessages(Set<String> nodes, ConfigurationSection section)
             // set current section
             currentSec = section.getConfigurationSection(messageNode);
 
-            // get message info from nodes
-            label = messageNode;
-            message = ChatColor.translateAlternateColorCodes('&', currentSec.getString("message"));
-            delay = currentSec.getInt("delay", 0);
+            // load message
+            current = loadMessageBase(messageNode, currentSec); // message base info
+            loadMessagePerms(current, currentSec); // includes and excludes perms
+            sender = loadMessageSender(current, currentSec); // message sender
 
-            // repeating message
+            // and finally, add/queue the message the message
             if (currentSec.contains("repeat"))
             {
-                repeat = currentSec.getInt("repeat"); // repeat specific
-
-                // create repeating message
-                current = new RepeatingMessage(this, label, message, delay, repeat);
+                startRepeatingMessage(current, sender, currentSec.getInt("repeat"));
             }
             else
             {
-                // create message
-                current = new Message(this, label, message, delay);
+                startMessage(current, sender);
             }
+        }
+    }
 
-            // let's add permission includes for the message now
-            if (currentSec.contains("includesperms"))
-            {
-                current.addPermissionsIncl(currentSec.getStringList("includesperms"));
-            }
+    /**
+     * Load the base message information from a message configuration section
+     * <p>
+     * Loads message string(s), delay, and message group order(random or not)
+     * </p>
+     *
+     * @param label          message label
+     * @param messageSection configuration section to load message info from
+     *
+     * @return message loaded from config
+     */
+    private Message loadMessageBase(String label, ConfigurationSection messageSection)
+    {
+        Message message;
+        // get message info from nodes
+        int delay = messageSection.getInt("delay", 0);
 
-            // let's add permission excludes for the message now
-            if (currentSec.contains("excludesperms"))
-            {
-                current.addPermissionsExcl(currentSec.getStringList("excludesperms"));
-            }
+        // message group
+        if (messageSection.contains("messages"))
+        {
+            List<String> messages = messageSection.getStringList("messages");
+            boolean random = messageSection.getBoolean("random-order", false);
+            message = new MessageGroup(this, label, messages, delay, random);
+        }
+        // regular message
+        else
+        {
+            String messageString = ChatColor.translateAlternateColorCodes('&', messageSection.getString("message"));
+            message = new Message(this, label, messageString, delay);
+        }
 
-            // get message sender
-            String senderString = currentSec.getString("sender", "chat").toLowerCase();
-            switch (senderString)
-            {
-                case "boss":
-                case "bossbar":
-                    sender = new BossBarSender(this,
-                            current,
-                            currentSec.getInt("bar.hold", 5),
-                            BarColor.valueOf(currentSec.getString("bar.color", "PURPLE").toUpperCase()),
-                            BarStyle.valueOf(currentSec.getString("bar.style", "SOLID").toUpperCase()),
-                            currentSec.getBoolean("bar.animate.enable", true),
-                            currentSec.getBoolean("bar.animate.reverse", false));
-                    break;
-                case "chat":
-                default:
-                    sender = new ChatMessageSender(this, current);
-                    break;
-            }
+        return message;
+    }
 
-            // and finally, add the message to our list
-            startMessage(current, sender);
+    /**
+     * Load permissions (includes and excludes) for a message from a message configuration section
+     *
+     * @param message        message to add permissions to
+     * @param messageSection configuration section to load permissions from
+     */
+    private void loadMessagePerms(Message message, ConfigurationSection messageSection)
+    {
+        // add permission includes for the message now
+        if (messageSection.contains("includesperms"))
+        {
+            message.addPermissionsIncl(messageSection.getStringList("includesperms"));
         }
+
+        // add permission excludes for the message now
+        if (messageSection.contains("excludesperms"))
+        {
+            message.addPermissionsExcl(messageSection.getStringList("excludesperms"));
+        }
+    }
+
+    /**
+     * Load message sender for a message from a message configuration section
+     *
+     * @param message        message to load sender for
+     * @param messageSection configuration section to load message sender config from
+     */
+    private MessageSender loadMessageSender(Message message, ConfigurationSection messageSection)
+    {
+        MessageSender sender;
+
+        // get message sender
+        String senderString = messageSection.getString("sender", "chat").toLowerCase();
+        switch (senderString)
+        {
+            case "boss":
+            case "bossbar":
+                sender = new BossBarSender(this,
+                        message,
+                        messageSection.getInt("bar.hold", 5),
+                        BarColor.valueOf(messageSection.getString("bar.color", "PURPLE").toUpperCase()),
+                        BarStyle.valueOf(messageSection.getString("bar.style", "SOLID").toUpperCase()),
+                        messageSection.getBoolean("bar.animate.enable", true),
+                        messageSection.getBoolean("bar.animate.reverse", false));
+                break;
+            case "chat":
+            default:
+                sender = new ChatMessageSender(this, message);
+                break;
+        }
+
+        return sender;
     }
 
     /**
@@ -254,15 +317,18 @@ private void addMessages(Set<String> nodes, ConfigurationSection section)
      */
     private void startMessage(Message message, MessageSender messageSender)
     {
-        if (message instanceof RepeatingMessage)
-        {
-            getServer().getScheduler().runTaskTimer(
-                    this, messageSender, message.getDelay() * 20L, ((RepeatingMessage) message).getPeriod() * 20L);
-        }
-        else
-        {
-            getServer().getScheduler().runTaskLater(this, messageSender, message.getDelay() * 20L);
-        }
+        getServer().getScheduler().runTaskLater(this, messageSender, message.getDelay() * 20);
+    }
+
+    /**
+     * Kick off/schedule repeating messages
+     *
+     * @param message       message we are starting
+     * @param messageSender sender for the message
+     */
+    private void startRepeatingMessage(Message message, MessageSender messageSender, int period)
+    {
+        getServer().getScheduler().runTaskTimer(this, messageSender, message.getDelay() * 20, period * 20);
     }
 
     @Override
diff --git a/src/main/java/org/simplemc/simpleannounce/message/Message.java b/src/main/java/org/simplemc/simpleannounce/message/Message.java
index 1d19003..c370b43 100755
--- a/src/main/java/org/simplemc/simpleannounce/message/Message.java
+++ b/src/main/java/org/simplemc/simpleannounce/message/Message.java
@@ -16,15 +16,17 @@ public class Message
 {
     private int delay; // delay in seconds for message
 
-    private Logger logger; // our logger
+    protected Logger logger; // our logger
     private String message, // message to send
             label; // unique message label
     private List<String> permissionIncludes, // permission nodes message receivers should include
             permissionExcludes; // permission nodes message receivers should exclude
 
     /**
-     * Create delayed message
+     * Create message
      *
+     * @param plugin  plugin instance
+     * @param label   message label from config
      * @param message message to send
      * @param delay   message's delay
      */
diff --git a/src/main/java/org/simplemc/simpleannounce/message/MessageGroup.java b/src/main/java/org/simplemc/simpleannounce/message/MessageGroup.java
new file mode 100755
index 0000000..d97e087
--- /dev/null
+++ b/src/main/java/org/simplemc/simpleannounce/message/MessageGroup.java
@@ -0,0 +1,64 @@
+package org.simplemc.simpleannounce.message;
+
+import org.simplemc.simpleannounce.SimpleAnnounce;
+
+import java.util.List;
+import java.util.Random;
+
+/**
+ * @author Taylor Becker
+ */
+public class MessageGroup extends Message
+{
+    private List<String> messages; // messages in this message group
+    private int current; // index of current message
+    private Random random; // random generator to use if messages are in random order
+
+    /**
+     * Create message
+     *
+     * @param plugin   plugin instance
+     * @param label    message label from config
+     * @param messages messages in this message group
+     * @param delay    message's delay
+     * @param random   whether the message group should run in random order
+     */
+    public MessageGroup(SimpleAnnounce plugin, String label, List<String> messages, int delay, boolean random)
+    {
+        super(plugin, label, "", delay);
+
+        this.messages = messages;
+
+        // init random if message is meant to be random
+        if (random)
+        {
+            this.random = new Random();
+        }
+
+        logger.finer(String.format("Message group %s created with %d messages. Random order? %b", label, messages.size(), random));
+    }
+
+    @Override
+    public String getMessage()
+    {
+        String message;
+
+        if (random != null)
+        {
+            message = messages.get(random.nextInt(messages.size()));
+        }
+        else
+        {
+            // get next message
+            message = messages.get(current++);
+
+            // if we've reached the end of the list, reset
+            if (current == messages.size())
+            {
+                current = 0;
+            }
+        }
+
+        return message;
+    }
+}
diff --git a/src/main/java/org/simplemc/simpleannounce/message/RepeatingMessage.java b/src/main/java/org/simplemc/simpleannounce/message/RepeatingMessage.java
deleted file mode 100755
index 4aea1a8..0000000
--- a/src/main/java/org/simplemc/simpleannounce/message/RepeatingMessage.java
+++ /dev/null
@@ -1,35 +0,0 @@
-package org.simplemc.simpleannounce.message;
-
-import org.simplemc.simpleannounce.SimpleAnnounce;
-
-/**
- * Repeating announcement message
- *
- * @author Taylor Becker
- */
-public class RepeatingMessage extends Message
-{
-    private int period; // period of the repeating message
-
-    /**
-     * Create delayed, repeating message
-     *
-     * @param message message to send
-     * @param delay   message's delay
-     * @param period  repeating period
-     */
-    public RepeatingMessage(SimpleAnnounce plugin, String label, String message, int delay, int period)
-    {
-        super(plugin, label, message, delay);
-
-        this.period = period;
-    }
-
-    /**
-     * @return repeating period
-     */
-    public int getPeriod()
-    {
-        return period;
-    }
-}
diff --git a/src/main/java/org/simplemc/simpleannounce/message/sender/BossBarSender.java b/src/main/java/org/simplemc/simpleannounce/message/sender/BossBarSender.java
index 9f3f8a9..856b530 100755
--- a/src/main/java/org/simplemc/simpleannounce/message/sender/BossBarSender.java
+++ b/src/main/java/org/simplemc/simpleannounce/message/sender/BossBarSender.java
@@ -8,7 +8,6 @@
 import org.bukkit.scheduler.BukkitTask;
 
 import org.simplemc.simpleannounce.message.Message;
-import org.simplemc.simpleannounce.message.RepeatingMessage;
 
 import java.util.Objects;
 
@@ -19,7 +18,9 @@
  */
 public class BossBarSender extends MessageSender
 {
-    private BossBar bossBar; // the boss bar
+    // boss bar config
+    private BarColor color; // color of the boss bar
+    private BarStyle style; // style of the boss bar
 
     private long holdTime; // amount of time message should stay on boss bar
     private boolean animate, // if the bar should animate or not(displaying remaining hold time)
@@ -41,19 +42,21 @@ public BossBarSender(Plugin plugin, Message message, int holdTime, BarColor colo
         super(plugin, message);
 
         this.holdTime = holdTime * 20L;
+        this.color = color;
+        this.style = style;
         this.animate = animate;
         this.reverse = reverse;
+    }
 
+    @Override
+    public void run()
+    {
         // create boss bar
-        bossBar = Bukkit.createBossBar(message.getMessage(), color, style);
+        BossBar bossBar = Bukkit.createBossBar(message.getMessage(), color, style);
 
         // set initial progress
         bossBar.setProgress(reverse ? 1 : 0);
-    }
 
-    @Override
-    public void run()
-    {
         // add all players that should receive the message to the boss bar
         Bukkit.getOnlinePlayers().stream()
                 .filter(Objects::nonNull)
@@ -77,14 +80,13 @@ public void run()
         }
 
         // schedule boss bar to go away
-        Runnable hideBossBar = message instanceof RepeatingMessage ? bossBar::hide : bossBar::removeAll;
         Bukkit.getScheduler().runTaskLaterAsynchronously(plugin, () ->
         {
             // reset progress
             bossBar.setProgress(reverse ? 1 : 0);
 
-            // hide bar
-            hideBossBar.run();
+            // remove bar
+            bossBar.removeAll();
 
             // cancel animation task
             if (animationTask != null)
diff --git a/src/main/resources/plugin.yml b/src/main/resources/plugin.yml
index 07a195a..f83d337 100755
--- a/src/main/resources/plugin.yml
+++ b/src/main/resources/plugin.yml
@@ -1,6 +1,6 @@
 name: SimpleAnnounce
 main: org.simplemc.simpleannounce.SimpleAnnounce
-version: 1.9.0
+version: 1.9.1
 website: http://SimpleMC.org/simpleannounce/
 author: Taylor Becker
 permissions: