How do you make it so that it rotate messages? 

Tried the below and always send first message 

"Auto Messages": [
    {
      "Permission": "smartchatbot.messages",
      "Message Frequency": "5m",
      "Auto Messages": [
        {
          "Is Enabled": true,
          "Message": "Do not mind, I am just a stupid bot."
	  "Message": "Message 2"
        }
      ]
    }
  ],​

Your configuration is invalid, consider using a JSON editor. Google some examples, take a look at other configurations. You should copy from { to } and put a ","

I tried with "," did not work

Merged post

Unless you mean...which seems strange that you would have to give permission each time ?? smartchatbot.messages

 

"Auto Messages": [
    {
      "Permission": "smartchatbot.messages",
      "Message Frequency": "35m",
      "Auto Messages": [
        {
          "Is Enabled": true,
          "Message": "MESSAGE !"
        }
      ]
    },
    {
      "Permission": "smartchatbot.messages",
      "Message Frequency": "60m",
      "Auto Messages": [
        {
          "Is Enabled": true,
          "Message": "MESSAGE 2"
        }
      ]
    },

You should copy from { to } within Auto Messages unless you want two independent broadcasts