diff --git a/crates/agent/src/context.rs b/crates/agent/src/context.rs
index 3c933717b9..57169de0af 100644
--- a/crates/agent/src/context.rs
+++ b/crates/agent/src/context.rs
@@ -2,7 +2,7 @@ use std::{ops::Range, sync::Arc};
 
 use gpui::{App, Entity, SharedString};
 use language::{Buffer, File};
-use language_model::{LanguageModelRequestMessage, MessageContent};
+use language_model::LanguageModelRequestMessage;
 use project::ProjectPath;
 use serde::{Deserialize, Serialize};
 use text::{Anchor, BufferId};
@@ -170,52 +170,61 @@ pub fn attach_context_to_message<'a>(
     let mut context_chunks = Vec::new();
 
     if !file_context.is_empty() {
-        context_chunks.push("The following files are available:\n");
+        context_chunks.push("<files>\n");
         for context in file_context {
             context_chunks.push(&context.context_buffer.text);
         }
+        context_chunks.push("\n</files>\n");
     }
 
     if !directory_context.is_empty() {
-        context_chunks.push("The following directories are available:\n");
+        context_chunks.push("<directories>\n");
         for context in directory_context {
             for context_buffer in &context.context_buffers {
                 context_chunks.push(&context_buffer.text);
             }
         }
+        context_chunks.push("\n</directories>\n");
     }
 
     if !symbol_context.is_empty() {
-        context_chunks.push("The following symbols are available:\n");
+        context_chunks.push("<symbols>\n");
         for context in symbol_context {
             context_chunks.push(&context.context_symbol.text);
         }
+        context_chunks.push("\n</symbols>\n");
     }
 
     if !fetch_context.is_empty() {
-        context_chunks.push("The following fetched results are available:\n");
+        context_chunks.push("<fetched_urls>\n");
         for context in &fetch_context {
             context_chunks.push(&context.url);
             context_chunks.push(&context.text);
         }
+        context_chunks.push("\n</fetched_urls>\n");
     }
 
     // Need to own the SharedString for summary so that it can be referenced.
     let mut thread_context_chunks = Vec::new();
     if !thread_context.is_empty() {
-        context_chunks.push("The following previous conversation threads are available:\n");
+        context_chunks.push("<conversation_threads>\n");
         for context in &thread_context {
             thread_context_chunks.push(context.summary(cx));
             thread_context_chunks.push(context.text.clone());
         }
+        context_chunks.push("\n</conversation_threads>\n");
     }
+
     for chunk in &thread_context_chunks {
         context_chunks.push(chunk);
     }
 
     if !context_chunks.is_empty() {
-        message
-            .content
-            .push(MessageContent::Text(context_chunks.join("\n")));
+        message.content.push(
+            "\n<context>\n\
+                The following items were attached by the user. You don't need to use other tools to read them.\n\n".into(),
+        );
+        message.content.push(context_chunks.join("\n").into());
+        message.content.push("\n</context>\n".into());
     }
 }
diff --git a/crates/agent/src/thread.rs b/crates/agent/src/thread.rs
index a2dd6da5d5..94d8376687 100644
--- a/crates/agent/src/thread.rs
+++ b/crates/agent/src/thread.rs
@@ -881,13 +881,9 @@ impl Thread {
             log::error!("system_prompt_context not set.")
         }
 
-        let mut referenced_context_ids = HashSet::default();
+        let mut added_context_ids = HashSet::<ContextId>::default();
 
         for message in &self.messages {
-            if let Some(context_ids) = self.context_by_message.get(&message.id) {
-                referenced_context_ids.extend(context_ids);
-            }
-
             let mut request_message = LanguageModelRequestMessage {
                 role: message.role,
                 content: Vec::new(),
@@ -907,6 +903,23 @@ impl Thread {
                 }
             }
 
+            // Attach context to this message if it's the first to reference it
+            if let Some(context_ids) = self.context_by_message.get(&message.id) {
+                let new_context_ids: Vec<_> = context_ids
+                    .iter()
+                    .filter(|id| !added_context_ids.contains(id))
+                    .collect();
+
+                if !new_context_ids.is_empty() {
+                    let referenced_context = new_context_ids
+                        .iter()
+                        .filter_map(|context_id| self.context.get(*context_id));
+
+                    attach_context_to_message(&mut request_message, referenced_context, cx);
+                    added_context_ids.extend(context_ids.iter());
+                }
+            }
+
             if !message.segments.is_empty() {
                 request_message
                     .content
@@ -933,21 +946,6 @@ impl Thread {
             message.cache = index == breakpoint_index;
         }
 
-        if !referenced_context_ids.is_empty() {
-            let mut context_message = LanguageModelRequestMessage {
-                role: Role::User,
-                content: Vec::new(),
-                cache: false,
-            };
-
-            let referenced_context = referenced_context_ids
-                .into_iter()
-                .filter_map(|context_id| self.context.get(context_id));
-            attach_context_to_message(&mut context_message, referenced_context, cx);
-
-            request.messages.push(context_message);
-        }
-
         self.attached_tracked_files_state(&mut request.messages, cx);
 
         request