diff --git a/frontend/src/main.js b/frontend/src/main.js
index e7ac424..91e3ffd 100644
--- a/frontend/src/main.js
+++ b/frontend/src/main.js
@@ -399,7 +399,7 @@ function renderChat() {
     chatMessagesEl.innerHTML = state.chatMessages
         .map(msg => `
             <div class="chat-message ${msg.role}">
-                ${escapeHtml(msg.content)}
+                ${DOMPurify.sanitize(marked.parse(msg.content || ''))}
             </div>
         `)
         .join('');
diff --git a/src/domain/agent/mod.rs b/src/domain/agent/mod.rs
index c00f517..1b6dde8 100644
--- a/src/domain/agent/mod.rs
+++ b/src/domain/agent/mod.rs
@@ -13,7 +13,7 @@ pub struct Agent {
     url: String,
     zen_api_key: Option<String>,
     tavily_api_key: Option<String>,
-    messages: Vec<Message>,
+    pub messages: Vec<Message>,
     tools: Option<Vec<Tool>>,
     logs: String,
     answer: Option<String>,
@@ -50,10 +50,19 @@ impl Agent {
             },
         ];
 
+        Self::with_messages(db, zen_api_key, tavily_api_key, messages)
+    }
+
+    pub fn with_messages(
+        db: DatabaseConnection,
+        zen_api_key: Option<String>,
+        tavily_api_key: Option<String>,
+        messages: Vec<Message>,
+    ) -> AppResult<Self> {
         let tools = Some(tools::get_tools());
 
         let client = reqwest::Client::builder()
-            .timeout(std::time::Duration::from_secs(60))
+            .timeout(std::time::Duration::from_secs(120))
             .build()
             .map_err(|e| AppError::Internal(format!("Failed to build HTTP client: {}", e)))?;
 
@@ -105,6 +114,35 @@ impl Agent {
                 turns, current_role
             ));
 
+            let assistant_message = self.execute_turn().await?;
+
+            if let Some(tool_calls) = &assistant_message.tool_calls {
+                if tool_calls.iter().any(|tc| tc.function.name == "answer") {
+                    finished = true;
+                }
+            }
+
+            if self.answer.is_some() {
+                finished = true;
+            }
+        }
+
+        self.log("\n--- Execution Finished ---");
+        Ok((self.logs.clone(), self.answer.clone()))
+    }
+
+    pub async fn execute_turn(&mut self) -> AppResult<Message> {
+        let max_sub_turns = 10;
+        let mut sub_turns = 0;
+
+        loop {
+            sub_turns += 1;
+            if sub_turns > max_sub_turns {
+                return Err(AppError::Internal(
+                    "Interaction cycle turn limit exceeded".into(),
+                ));
+            }
+
             let chat_response = self.call_llm().await?;
             let assistant_message = chat_response
                 .choices
@@ -121,20 +159,24 @@ impl Agent {
                 }
             }
 
-            if let Some(tool_calls) = assistant_message.tool_calls {
+            if let Some(tool_calls) = &assistant_message.tool_calls {
+                let mut is_final_cycle = false;
+                let mut final_answer = None;
+
                 for tool_call in tool_calls {
                     self.log(&format!("Calling tool: {}", tool_call.function.name));
 
                     let (tool_message, is_final, tool_answer) =
-                        tools::handle_tool_call(&tool_call, &self.tavily_api_key, &self.db)
+                        tools::handle_tool_call(tool_call, &self.tavily_api_key, &self.db)
                             .await
                             .map_err(|e| {
                                 AppError::Internal(format!("Tool execution failed: {}", e))
                             })?;
 
                     if let Some(ans) = tool_answer {
-                        self.answer = Some(ans);
-                        self.log("Task marked as finished by tool.");
+                        self.answer = Some(ans.clone());
+                        final_answer = Some(ans);
+                        self.log("Interaction marked as finished by tool.");
                     }
 
                     if let Some(content) = &tool_message.content {
@@ -143,20 +185,24 @@ impl Agent {
 
                     self.messages.push(tool_message);
                     if is_final {
-                        finished = true;
+                        is_final_cycle = true;
                     }
                 }
-            } else if assistant_message.content.is_some() {
-                // If assistant just talked without tools, we might be stuck or finished.
-                // But typically we expect a 'finish' tool call.
-                self.log("Assistant responded without tool calls.");
-                // For now we continue unless the assistant explicitly uses a tool to finish,
-                // or we could add heuristic here if needed.
-            }
-        }
 
-        self.log("\n--- Execution Finished ---");
-        Ok((self.logs.clone(), self.answer.clone()))
+                if is_final_cycle {
+                    return Ok(Message {
+                        role: "assistant".to_string(),
+                        content: final_answer.or(assistant_message.content),
+                        tool_calls: None,
+                        tool_call_id: None,
+                    });
+                }
+
+                continue;
+            }
+
+            return Ok(assistant_message);
+        }
     }
 
     async fn call_llm(&self) -> AppResult<ChatResponse> {
@@ -172,23 +218,46 @@ impl Agent {
             request_builder = request_builder.header("Authorization", format!("Bearer {}", key));
         }
 
-        let response = request_builder.send().await.map_err(AppError::Network)?;
+        let start = std::time::Instant::now();
+        let response = request_builder.send().await.map_err(|e| {
+            let duration = start.elapsed();
+            let is_timeout = e.is_timeout();
+            tracing::error!(
+                "Network error after {:?} during LLM call (Timeout: {}): {:?}",
+                duration,
+                is_timeout,
+                e
+            );
+            AppError::Network(e)
+        })?;
+
+        let duration = start.elapsed();
+        tracing::info!("LLM request completed in {:?}", duration);
 
         if !response.status().is_success() {
             let status = response.status();
-            let error_text = response
+            let body_text = response
                 .text()
                 .await
-                .unwrap_or_else(|_| "Unknown error".into());
-            return Err(AppError::Internal(format!(
-                "API request failed: {} - {}",
-                status, error_text
-            )));
+                .unwrap_or_else(|_| "Unknown body".into());
+            let err = format!("API request failed: {} - {}", status, body_text);
+            tracing::error!("{}", err);
+            return Err(AppError::Internal(err));
         }
 
-        response
-            .json()
-            .await
-            .map_err(|e| AppError::Internal(format!("Failed to parse LLM response: {}", e)))
+        let response_text = response.text().await.map_err(|e| {
+            let err = format!("Failed to read response text: {}", e);
+            tracing::error!("{}", err);
+            AppError::Internal(err)
+        })?;
+
+        serde_json::from_str(&response_text).map_err(|e| {
+            let err = format!(
+                "Failed to parse LLM response: {} | Raw Body: {}",
+                e, response_text
+            );
+            tracing::error!("{}", err);
+            AppError::Internal(err)
+        })
     }
 }
diff --git a/src/server/chat.rs b/src/server/chat.rs
index 6e46350..5163275 100644
--- a/src/server/chat.rs
+++ b/src/server/chat.rs
@@ -1,4 +1,4 @@
-use crate::domain::agent::api::{ChatRequest, ChatResponse, Message};
+use crate::domain::agent::api::Message;
 use crate::error::AppError;
 use crate::server::AppState;
 use axum::{Json, extract::State};
@@ -22,109 +22,36 @@ pub async fn chat_handler(
     let msg_count = payload.messages.len();
     tracing::info!("Received chat request with {} messages", msg_count);
 
-    let client = reqwest::Client::builder()
-        .timeout(std::time::Duration::from_secs(60))
-        .build()
-        .map_err(|e| {
-            let err = format!("Failed to build HTTP client: {}", e);
-            tracing::error!("{}", err);
-            AppError::Internal(err)
-        })?;
-
-    let url = "https://opencode.ai/zen/v1/chat/completions";
     let mut messages = payload.messages;
-    let tools = crate::domain::agent::tools::get_tools();
 
-    let max_turns = 10;
-    let mut turns = 0;
+    // Inject current date awareness if not already present or as a fresh system message
+    let now = chrono::Local::now();
+    let date_str = now.format("%A, %B %e, %Y at %l:%M %P").to_string();
+    messages.insert(
+        0,
+        Message {
+            role: "system".to_string(),
+            content: Some(format!(
+                "The current date and time is {}. Today is {}. You are in interactive chat mode.",
+                date_str,
+                now.format("%Y-%m-%d")
+            )),
+            tool_calls: None,
+            tool_call_id: None,
+        },
+    );
 
-    loop {
-        turns += 1;
-        if turns > max_turns {
-            return Err(AppError::Internal("Chat turn limit exceeded".into()));
-        }
+    let mut agent = crate::domain::agent::Agent::with_messages(
+        state.db.clone(),
+        state.config.zen_api_key.clone(),
+        state.config.tavily_api_key.clone(),
+        messages,
+    )?;
 
-        let request = ChatRequest {
-            model: "big-pickle".to_string(),
-            messages: messages.clone(),
-            tools: Some(tools.clone()),
-        };
+    tracing::info!("Starting interactive agent turn");
+    let assistant_message = agent.execute_turn().await?;
 
-        let mut request_builder = client.post(url).json(&request);
-
-        if let Some(key) = &state.config.zen_api_key {
-            request_builder = request_builder.header("Authorization", format!("Bearer {}", key));
-        }
-
-        let response = request_builder.send().await.map_err(|e| {
-            tracing::error!("Network error during chat completion: {}", e);
-            AppError::Network(e)
-        })?;
-
-        if !response.status().is_success() {
-            let status = response.status();
-            let error_text = response
-                .text()
-                .await
-                .unwrap_or_else(|_| "Unknown error".into());
-            let err = format!("API request failed: {} - {}", status, error_text);
-            tracing::error!("{}", err);
-            return Err(AppError::Internal(err));
-        }
-
-        let chat_response: ChatResponse = response.json().await.map_err(|e| {
-            let err = format!("Failed to parse LLM response: {}", e);
-            tracing::error!("{}", err);
-            AppError::Internal(err)
-        })?;
-
-        let assistant_message = chat_response
-            .choices
-            .get(0)
-            .ok_or_else(|| {
-                let err = "Missing assistant response choices";
-                tracing::error!("{}", err);
-                AppError::Internal(err.into())
-            })?
-            .message
-            .clone();
-
-        messages.push(assistant_message.clone());
-
-        if let Some(tool_calls) = &assistant_message.tool_calls {
-            for tool_call in tool_calls {
-                tracing::info!("Chat agent calling tool: {}", tool_call.function.name);
-                let (tool_message, is_final, answer) =
-                    crate::domain::agent::tools::handle_tool_call(
-                        tool_call,
-                        &state.config.tavily_api_key,
-                        &state.db,
-                    )
-                    .await
-                    .map_err(|e| AppError::Internal(format!("Tool execution failed: {}", e)))?;
-
-                messages.push(tool_message.clone());
-
-                if is_final {
-                    tracing::info!("Chat agent finished via tool");
-                    return Ok(Json(ChatResult {
-                        message: Message {
-                            role: "assistant".to_string(),
-                            content: answer.or(tool_message.content),
-                            tool_calls: None,
-                            tool_call_id: None,
-                        },
-                    }));
-                }
-            }
-            // After tool calls, we loop back to get another assistant response
-            continue;
-        }
-
-        // If no tool calls, it's a final response for this turn
-        tracing::info!("Chat completion successful");
-        return Ok(Json(ChatResult {
-            message: assistant_message,
-        }));
-    }
+    Ok(Json(ChatResult {
+        message: assistant_message,
+    }))
 }