Im trying to make sense of the config file but cant really.

The default config was working with the "this bot works" stuff but how do I actually add multiple words?

Also it doesnt say anything when I type "wipe" or "when wipe" etc. What am I doing wrong?

{
  "Chat Prefix": "<color=#787FFF>Bot </color>",
  "Bot Icon (SteamID)": 0,
  "Cooldown Between Auto Responses For User": "10s",
  "Global Cooldown Between Auto Responses": "2s",
  "Use Default Chat (0), Chat Plus (1), Better Chat (2)": 2,
  "Debug": false,
  "Allow Multiple Auto Responses": false,
  "Minimal Time Between Message And Answer": 1,
  "Maximal Time Between Message And Answer": 5,
  "Joining Message": [
    "Welcome, {name} ({id}, {ip})!",
    "Hello, dear {name} ({id}, {ip})!"
  ],
  "Leaving Message": [
    "Bye, {name} ({id}, {ip})!\nReason: {reason}",
    "{name} ({id}, {ip}) left the game. Reason: {reason}"
  ],
  "Joining Message Enabled": false,
  "Leaving Message Enabled": false,
  "Auto Messages": [
    {
      "Permission": "smartchatbot.messages",
      "Message Frequency": "5m",
      "Auto Messages": [
        {
          "Is Enabled": false,
          "Message": "Do not mind, I am just a stupid bot."
        }
      ]
    }
  ],
  "Auto Responses": [
    {
      "Permission": "smartchatbot.response",
      "Auto Responses": [
        {
          "Is Enabled": true,
          "Remove Message From Sender": false,
          "Send Response For Everyone (true) or Only For Sender (false)": true,
          "Triggers": [
            {
              "Percentage Of Contained Words": 0.75,
              "Regex Enabled": false,
              "Words": [
                "When wipe",
                "wiped",
                "wipe",
                "server wipe"
              ]
            }
          ],
          "Answers": [
            "The wipe is every thursday (usually in the morning CET/GMT+1. Monthly wipes along with the Rust update usually happen in the evening CET/GMT+1.",
            "The wipe is every thursday (usually in the morning CET/GMT+1. Monthly wipes along with the Rust update usually happen in the evening CET/GMT+1."
          ]
        }
      ]
    }
  ]
}

Maybe default configuration does not work because you forgot about permissions?

No the default was working because I had all the this bot works messages

Your problem is in percentage of contained words. In your example your message must contain 3 of 4 entries in the config (

"When wipe",
                "wiped",
                "wipe",
                "server wipe"​

)

If you need to use only 1 of 4 values, just use percentage 0.25