diff --git a/backend/danswer/llm/answering/answer.py b/backend/danswer/llm/answering/answer.py
index 684b0aab7..7e7733cc0 100644
--- a/backend/danswer/llm/answering/answer.py
+++ b/backend/danswer/llm/answering/answer.py
@@ -248,6 +248,13 @@ class Answer:
                         if self.is_cancelled:
                             return
                         yield cast(str, message.content)
+                    if (
+                        message.additional_kwargs.get("usage_metadata", {}).get("stop")
+                        == "length"
+                    ):
+                        yield StreamStopInfo(
+                            stop_reason=StreamStopReason.CONTEXT_LENGTH
+                        )
 
             if not tool_call_chunk:
                 return  # no tool call needed
diff --git a/web/src/app/chat/ChatPage.tsx b/web/src/app/chat/ChatPage.tsx
index 57c663af2..0c63ad216 100644
--- a/web/src/app/chat/ChatPage.tsx
+++ b/web/src/app/chat/ChatPage.tsx
@@ -99,7 +99,6 @@ import ExceptionTraceModal from "@/components/modals/ExceptionTraceModal";
 
 import { SEARCH_TOOL_NAME } from "./tools/constants";
 import { useUser } from "@/components/user/UserProvider";
-import { Stop } from "@phosphor-icons/react";
 
 const TEMP_USER_MESSAGE_ID = -1;
 const TEMP_ASSISTANT_MESSAGE_ID = -2;
diff --git a/web/src/app/chat/message/Messages.tsx b/web/src/app/chat/message/Messages.tsx
index fa307ec93..ff177c6a6 100644
--- a/web/src/app/chat/message/Messages.tsx
+++ b/web/src/app/chat/message/Messages.tsx
@@ -364,7 +364,7 @@ export const AIMessage = ({
                         <FileDisplay files={files || []} />
 
                         {typeof content === "string" ? (
-                          <div className="overflow-x-visible w-full pr-2">
+                          <div className="overflow-x-visible max-w-content-max">
                             <ReactMarkdown
                               key={messageId}
                               className="prose max-w-full text-base"
diff --git a/web/src/app/globals.css b/web/src/app/globals.css
index 084d4715a..fdb9d7985 100644
--- a/web/src/app/globals.css
+++ b/web/src/app/globals.css
@@ -230,3 +230,10 @@ form {
   gap: 1.2rem;
   align-items: start;
 }
+
+ol > li > p,
+ul > li > p {
+  margin-top: 0;
+  margin-bottom: 0;
+  display: inline; /* Make paragraphs inline to reduce vertical space */
+}
diff --git a/web/tailwind-themes/tailwind.config.js b/web/tailwind-themes/tailwind.config.js
index f2d7601fd..1cac0c877 100644
--- a/web/tailwind-themes/tailwind.config.js
+++ b/web/tailwind-themes/tailwind.config.js
@@ -65,6 +65,7 @@ module.exports = {
       maxWidth: {
         "document-sidebar": "1000px",
         "message-max": "850px",
+        "content-max": "725px",
         "searchbar-max": "800px",
       },
       colors: {