diff --git a/crates/prompt_gateway/src/hallucination.rs b/crates/prompt_gateway/src/hallucination.rs
index 5c82c1ae..a17c6f60 100644
--- a/crates/prompt_gateway/src/hallucination.rs
+++ b/crates/prompt_gateway/src/hallucination.rs
@@ -104,4 +104,58 @@ mod test {
         println!("{:?}", messages_for_halluncination);
         assert_eq!(messages_for_halluncination.len(), 3);
     }
+    #[test]
+    fn test_hallucination_message_long() {
+        let test_str = r#"
+      [
+        {
+          "role": "system",
+          "model" : "gpt-3.5-turbo",
+          "content": "You are a helpful assistant.\n\n# Tools\n\nYou may call one or more functions to assist with the user query.\n\nYou are provided with function signatures within <tools></tools> XML tags:\n<tools>\n{\"type\": \"function\", \"function\": {\"name\": \"headcount\", \"description\": \"Get headcount data for a region by staffing type\", \"parameters\": {\"properties\": {\"staffing_type\": {\"type\": \"str\", \"description\": \"The staffing type like contract, fte or agency\"}, \"region\": {\"type\": \"str\", \"description\": \"the geographical region for which you want headcount data.\"}}, \"required\": [\"staffing_type\", \"region\"]}}}\n</tools>\n\nFor each function call, return a json object with function name and arguments within <tool_call></tool_call> XML tags:\n<tool_call>\n{\"name\": <function-name>, \"arguments\": <args-json-object>}\n</tool_call>"
+        },
+        { "role": "user", "content": "Hello" },
+        {
+          "role": "assistant",
+          "model": "gpt-3.5-turbo",
+          "content": "Hi there!"
+        },
+        { "role": "user", "content": "tell me about headcount data" },
+        {
+          "role": "assistant",
+          "model": "Arch-Function-1.5B",
+          "content": "The \"headcount\" tool provides information about the number of employees in a specific region based on the type of staffing used. It requires two parameters: \"staffing_type\" and \"region\". The \"staffing_type\" parameter specifies the type of staffing, such as contract, full-time equivalent (fte), or agency. The \"region\" parameter specifies the geographical region for which you want headcount data."
+        },
+        { "role": "user", "content": "europe" },
+        {
+          "role": "system",
+          "model": "Arch-Function-1.5B",
+          "content": "It seems like you are asking for headcount data for Europe. Could you please specify the staffing type?"
+        },
+        { "role": "user", "content": "fte" },
+        {
+          "role": "assistant",
+          "model": "gpt-3.5-turbo",
+          "content": "The headcount is 50000"
+        },
+        { "role": "user", "content": "tell me about the weather" },
+        {
+          "role": "assistant",
+          "model": "Arch-Function-1.5B",
+          "content" : "The weather forcast tools requires 2 parameters: city and days. Please specify"
+        },
+        { "role": "user", "content": "Seattle" },
+        {
+          "role": "system",
+          "model": "Arch-Function-1.5B",
+          "content": "It seems like you are asking for weather data for Seattle. Could you please specify the days?"
+        },
+        { "role": "user", "content": "7 days" }
+      ]
+      "#;
+
+        let messages: Vec<Message> = serde_json::from_str(test_str).unwrap();
+        let messages_for_halluncination = extract_messages_for_hallucination(&messages);
+        println!("{:?}", messages_for_halluncination);
+        assert_eq!(messages_for_halluncination.len(), 3);
+    }
 }