diff --git a/crates/Cargo.lock b/crates/Cargo.lock
index 4a76be14..a9c06a49 100644
--- a/crates/Cargo.lock
+++ b/crates/Cargo.lock
@@ -1120,6 +1120,7 @@ dependencies = [
  "http",
  "log",
  "md5",
+ "pretty_assertions",
  "proxy-wasm",
  "proxy-wasm-test-framework",
  "rand",
diff --git a/crates/prompt_gateway/Cargo.toml b/crates/prompt_gateway/Cargo.toml
index 29d385b7..e8a166f8 100644
--- a/crates/prompt_gateway/Cargo.toml
+++ b/crates/prompt_gateway/Cargo.toml
@@ -26,3 +26,4 @@ sha2 = "0.10.8"
 [dev-dependencies]
 proxy-wasm-test-framework = { git = "https://github.com/katanemo/test-framework.git", branch = "new" }
 serial_test = "3.1.1"
+pretty_assertions = "1.4.1"
diff --git a/crates/prompt_gateway/src/hallucination.rs b/crates/prompt_gateway/src/hallucination.rs
index 71d1e7cf..62b119ac 100644
--- a/crates/prompt_gateway/src/hallucination.rs
+++ b/crates/prompt_gateway/src/hallucination.rs
@@ -1,31 +1,63 @@
-use common::{common_types::open_ai::Message, consts::USER_ROLE};
+use common::{
+    common_types::open_ai::Message,
+    consts::{ARCH_MODEL_PREFIX, ASSISTANT_ROLE, USER_ROLE},
+};
 
-pub fn extract_messages_for_hallucination(messages: &[Message]) -> Vec<String> {
-    let all_user_messages = messages
-        .iter()
-        .filter(|m| m.role == USER_ROLE)
-        .map(|m| m.content.as_ref().unwrap().clone())
-        .collect::<Vec<String>>();
-    all_user_messages
+pub fn extract_messages_for_hallucination(messages: &Vec<Message>) -> Vec<String> {
+    let mut arch_assistant = false;
+    let mut user_messages = Vec::new();
+    if messages.len() >= 2 {
+        let latest_assistant_message = &messages[messages.len() - 2];
+        if let Some(model) = latest_assistant_message.model.as_ref() {
+            if model.starts_with(ARCH_MODEL_PREFIX) {
+                arch_assistant = true;
+            }
+        }
+    }
+    if arch_assistant {
+        for message in messages.iter().rev() {
+            if let Some(model) = message.model.as_ref() {
+                if !model.starts_with(ARCH_MODEL_PREFIX) {
+                    if message.role == ASSISTANT_ROLE {
+                        break;
+                    }
+                }
+            }
+            if message.role == USER_ROLE {
+                if let Some(content) = &message.content {
+                    user_messages.push(content.clone());
+                }
+            }
+        }
+    } else if let Some(message) = messages.last() {
+        if let Some(content) = &message.content {
+            user_messages.push(content.clone());
+        }
+    }
+    user_messages.reverse(); // Reverse to maintain the original order
+    return user_messages;
 }
 
 #[cfg(test)]
 mod test {
+    use pretty_assertions::assert_eq;
     use common::common_types::open_ai::Message;
 
     use super::extract_messages_for_hallucination;
 
     #[test]
-    fn test_hallucination_message() {
+    fn test_hallucination_message_simple() {
         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": "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 and for fte" }
@@ -36,4 +68,97 @@ mod test {
         let messages_for_halluncination = extract_messages_for_hallucination(&messages);
         assert_eq!(messages_for_halluncination.len(), 2);
     }
+    #[test]
+    fn test_hallucination_message_medium() {
+        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" }
+      ]
+      "#;
+
+        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);
+    }
+    #[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);
+        assert_eq!(["tell me about the weather", "Seattle", "7 days"], messages_for_halluncination.as_slice());
+    }
+
 }