diff --git a/lib/cadet_web/controllers/chat_controller.ex b/lib/cadet_web/controllers/chat_controller.ex
index e39271ea4..030c7cd3a 100644
--- a/lib/cadet_web/controllers/chat_controller.ex
+++ b/lib/cadet_web/controllers/chat_controller.ex
@@ -6,6 +6,7 @@ defmodule CadetWeb.ChatController do
   use PhoenixSwagger
 
   alias Cadet.Chatbot.{Conversation, LlmConversations}
+  @max_content_size 1000
 
   def init_chat(conn, %{"section" => section, "initialContext" => initialContext}) do
     user = conn.assigns.current_user
@@ -21,7 +22,8 @@ defmodule CadetWeb.ChatController do
             "conversation_init.json",
             %{
               conversation_id: conversation.id,
-              last_message: conversation.messages |> List.last()
+              last_message: conversation.messages |> List.last(),
+              max_content_size: @max_content_size
             }
           )
 
@@ -51,13 +53,15 @@ defmodule CadetWeb.ChatController do
     response(200, "OK")
     response(400, "Missing or invalid parameter(s)")
     response(401, "Unauthorized")
+    response(422, "Message exceeds the maximum allowed length")
     response(500, "When OpenAI API returns an error")
   end
 
   def chat(conn, %{"conversationId" => conversation_id, "message" => user_message}) do
     user = conn.assigns.current_user
 
-    with {:ok, conversation} <-
+    with true <- String.length(user_message) <= @max_content_size || {:error, :message_too_long},
+         {:ok, conversation} <-
            LlmConversations.get_conversation_for_user(user.id, conversation_id),
          {:ok, updated_conversation} <-
            LlmConversations.add_message(conversation, "user", user_message),
@@ -85,6 +89,13 @@ defmodule CadetWeb.ChatController do
           send_resp(conn, 500, error_message)
       end
     else
+      {:error, :message_too_long} ->
+        send_resp(
+          conn,
+          :unprocessable_entity,
+          "Message exceeds the maximum allowed length of #{@max_content_size}"
+        )
+
       {:error, {:not_found, error_message}} ->
         send_resp(conn, :not_found, error_message)
 
@@ -107,4 +118,6 @@ defmodule CadetWeb.ChatController do
 
     conversation.prepend_context ++ messages_payload
   end
+
+  def max_content_length, do: @max_content_size
 end
diff --git a/lib/cadet_web/views/chat_view.ex b/lib/cadet_web/views/chat_view.ex
index b7db0bd2b..8dc72727a 100644
--- a/lib/cadet_web/views/chat_view.ex
+++ b/lib/cadet_web/views/chat_view.ex
@@ -1,8 +1,12 @@
 defmodule CadetWeb.ChatView do
   use CadetWeb, :view
 
-  def render("conversation_init.json", %{conversation_id: id, last_message: last}) do
-    %{conversationId: id, response: last}
+  def render("conversation_init.json", %{
+        conversation_id: id,
+        last_message: last,
+        max_content_size: size
+      }) do
+    %{conversationId: id, response: last, maxContentSize: size}
   end
 
   def render("conversation.json", %{conversation_id: id, response: response}) do
diff --git a/test/cadet_web/controllers/chat_controller_test.exs b/test/cadet_web/controllers/chat_controller_test.exs
index e5f63f164..b8c0c6808 100644
--- a/test/cadet_web/controllers/chat_controller_test.exs
+++ b/test/cadet_web/controllers/chat_controller_test.exs
@@ -76,6 +76,41 @@ defmodule CadetWeb.ChatControllerTest do
       end
     end
 
+    @tag authenticate: :student
+    @tag requires_setup: true
+    test "The content length is too long",
+         %{conn: conn, conversation_id: conversation_id} do
+      assert conversation_id != nil
+      max_message_length = ChatController.max_content_length()
+      message_exceed_length = String.duplicate("a", max_message_length + 1)
+
+      conn =
+        post(conn, "/v2/chats/#{conversation_id}/message", %{
+          "conversation_id" => conversation_id,
+          "message" => "#{message_exceed_length}"
+        })
+
+      assert response(conn, :unprocessable_entity) ==
+               "Message exceeds the maximum allowed length of #{max_message_length}"
+    end
+
+    @tag authenticate: :student
+    @tag requires_setup: true
+    test "The content length less than the maximum allowed length but conversation belongs to another user",
+         %{conn: conn, conversation_id: conversation_id} do
+      assert conversation_id != nil
+      max_message_length = ChatController.max_content_length()
+      message_exceed_length = String.duplicate("a", max_message_length)
+
+      conn =
+        post(conn, "/v2/chats/#{conversation_id}/message", %{
+          "conversation_id" => conversation_id,
+          "message" => "#{message_exceed_length}"
+        })
+
+      assert response(conn, :not_found) == "Conversation not found"
+    end
+
     @tag authenticate: :student
     test "invalid conversation id", %{conn: conn} do
       conversation_id = "-1"