diff --git a/frontend-web/src/components/workspace/messages/message-list-item.tsx b/frontend-web/src/components/workspace/messages/message-list-item.tsx
index 48ad91e0..5d46e258 100644
--- a/frontend-web/src/components/workspace/messages/message-list-item.tsx
+++ b/frontend-web/src/components/workspace/messages/message-list-item.tsx
@@ -1,13 +1,13 @@
 import type { Message } from "@langchain/langgraph-sdk";
 import { ClockIcon, FileIcon, Loader2Icon } from "lucide-react";
-import {
-  memo,
-  useCallback,
-  useContext,
-  useMemo,
-  type AnchorHTMLAttributes,
-  type ImgHTMLAttributes,
-} from "react";
+import {
+  memo,
+  useCallback,
+  useContext,
+  useMemo,
+  type AnchorHTMLAttributes,
+  type ImgHTMLAttributes,
+} from "react";
 import rehypeKatex from "rehype-katex";
 
 import { Loader } from "@/components/ai-elements/loader";
@@ -116,19 +116,21 @@ function useArtifactResolver(threadId: string): (path: string) => string {
   );
 }
 
-export function MessageListItem({
-  className,
-  message,
-  isLoading,
-  threadId,
-  tokenUsageEnabled = false,
+export function MessageListItem({
+  className,
+  fitRowToContent = false,
+  message,
+  isLoading,
+  threadId,
+  tokenUsageEnabled = false,
   displaySources = [],
   extraRehypePlugins,
-}: {
-  className?: string;
-  message: Message;
-  isLoading?: boolean;
-  threadId: string;
+}: {
+  className?: string;
+  fitRowToContent?: boolean;
+  message: Message;
+  isLoading?: boolean;
+  threadId: string;
   tokenUsageEnabled?: boolean;
   displaySources?: RuntimeDisplaySource[];
   extraRehypePlugins?: ReturnType<typeof useRehypeSplitWordsIntoSpans>;
@@ -138,11 +140,16 @@ export function MessageListItem({
     extractContentFromMessage(message) ??
     extractReasoningContentFromMessage(message) ??
     "";
-  return (
-    <AIElementMessage
-      className={cn("group/conversation-message relative w-full", className)}
-      from={isHuman ? "user" : "assistant"}
-    >
+  return (
+    <AIElementMessage
+      className={cn(
+        "group/conversation-message relative",
+        fitRowToContent ? "max-w-full w-fit" : "w-full",
+        isHuman && fitRowToContent && "ml-auto",
+        className,
+      )}
+      from={isHuman ? "user" : "assistant"}
+    >
       <MessageContent
         className={isHuman ? "w-fit" : "w-full"}
         message={message}
@@ -343,20 +350,20 @@ function MessageContent_({
       </AIElementMessageResponse>
     ) : null;
     return (
-      <div className={cn("ml-auto flex flex-col gap-2", className)}>
+      <div className={cn("ml-auto flex max-w-full min-w-0 flex-col items-end gap-2", className)}>
         {filesList}
-        {parsedHumanContent.pageContext ? (
-          <EmbeddedPageContextCard pageContext={parsedHumanContent.pageContext} />
-        ) : null}
         {messageResponse && (
-          <AIElementMessageContent className="w-fit">
+          <AIElementMessageContent className="min-w-0 max-w-full w-fit">
             {messageResponse}
           </AIElementMessageContent>
         )}
-        <MessageTimeStamp time={messageTime} align="right" />
-      </div>
-    );
-  }
+        {parsedHumanContent.pageContext ? (
+          <EmbeddedPageContextCard pageContext={parsedHumanContent.pageContext} />
+        ) : null}
+        <MessageTimeStamp time={messageTime} align="right" />
+      </div>
+    );
+  }
 
   return (
     <AIElementMessageContent className={className}>
@@ -388,33 +395,22 @@ function EmbeddedPageContextCard({
 }: {
   pageContext: EmbeddedPageContext;
 }) {
+  const previewText = [pageContext.title, pageContext.url, pageContext.content]
+    .filter(Boolean)
+    .join(" | ");
+
   return (
-    <div className="bg-muted/70 ml-auto flex max-w-sm flex-col gap-2 rounded-2xl border px-3 py-2 text-sm shadow-sm">
-      {pageContext.title ? (
-        <div className="truncate font-medium" title={pageContext.title}>
-          {pageContext.title}
-        </div>
-      ) : null}
-      {pageContext.url ? (
-        <a
-          className="text-muted-foreground block truncate text-xs underline underline-offset-2"
-          href={pageContext.url}
-          target="_blank"
-          rel="noopener noreferrer"
-          title={pageContext.url}
-        >
-          {pageContext.url}
-        </a>
-      ) : null}
-      {pageContext.content ? (
-        <div className="text-muted-foreground truncate text-xs" title={pageContext.content}>
-          {pageContext.content}
-        </div>
-      ) : null}
+    <div className="bg-muted/70 ml-auto flex w-fit min-w-0 max-w-[min(24rem,calc(100vw-2rem),100%)] flex-col gap-2 rounded-2xl border px-3 py-2 text-sm shadow-sm">
+      <div
+        className="text-muted-foreground line-clamp-2 min-w-0 [overflow-wrap:anywhere] break-words text-xs"
+        title={previewText}
+      >
+        {previewText}
+      </div>
     </div>
   );
 }
-
+
 /**
  * Format a wall-clock message time as ``YYYY-MM-DD HH:mm`` for display, plus a
  * full localized string for the hover title. Returns ``null`` when no/invalid
@@ -506,7 +502,7 @@ function isImageFile(filename: string): boolean {
  * Format bytes to human-readable size string
  */
 function formatBytes(bytes: number): string {
-  if (bytes === 0) return "—";
+  if (bytes === 0) return "0 B";
   const kb = bytes / 1024;
   if (kb < 1024) return `${kb.toFixed(1)} KB`;
   return `${(kb / 1024).toFixed(1)} MB`;
@@ -795,3 +791,4 @@ function groupDisplaySources(sources: RuntimeDisplaySource[]) {
 function normalizeName(name: string) {
   return name.toLowerCase().replace(/[^a-z0-9]+/g, "");
 }
+
diff --git a/frontend-web/src/components/workspace/messages/message-list.tsx b/frontend-web/src/components/workspace/messages/message-list.tsx
index 33463bf9..e1d8527b 100644
--- a/frontend-web/src/components/workspace/messages/message-list.tsx
+++ b/frontend-web/src/components/workspace/messages/message-list.tsx
@@ -50,22 +50,26 @@ import { SubtaskCard } from "./subtask-card";
 export const MESSAGE_LIST_DEFAULT_PADDING_BOTTOM = 160;
 export const MESSAGE_LIST_FOLLOWUPS_EXTRA_PADDING_BOTTOM = 80;
 
-export function MessageList({
-  className,
-  threadId,
-  thread,
-  paddingBottom = MESSAGE_LIST_DEFAULT_PADDING_BOTTOM,
-  tokenUsageEnabled = false,
+export function MessageList({
+  className,
+  contentClassName,
+  fitMessageRowsToContent = false,
+  threadId,
+  thread,
+  paddingBottom = MESSAGE_LIST_DEFAULT_PADDING_BOTTOM,
+  tokenUsageEnabled = false,
   extraRehypePlugins,
   onClarificationSubmit,
   onSetupAgentApprove,
   onSetupAgentReject,
-}: {
-  className?: string;
-  threadId: string;
-  thread: BaseStream<AgentThreadState>;
-  paddingBottom?: number;
-  tokenUsageEnabled?: boolean;
+}: {
+  className?: string;
+  contentClassName?: string;
+  fitMessageRowsToContent?: boolean;
+  threadId: string;
+  thread: BaseStream<AgentThreadState>;
+  paddingBottom?: number;
+  tokenUsageEnabled?: boolean;
   extraRehypePlugins?: ReturnType<typeof useRehypeSplitWordsIntoSpans>;
   onClarificationSubmit?: (answer: string) => void | Promise<void>;
   onSetupAgentApprove?: (payload: SetupAgentApprovalPayload) => void | Promise<void>;
@@ -213,12 +217,17 @@ export function MessageList({
   if (thread.isThreadLoading && messages.length === 0) {
     return <MessageListSkeleton />;
   }
-  return (
-    <Conversation
-      className={cn("flex size-full flex-col justify-center", className)}
-    >
-      <ConversationContent className="mx-auto w-full max-w-(--container-width-lg) gap-8 pt-12">
-        <MessageMetricsProvider messages={messages} isLoading={thread.isLoading}>
+  return (
+    <Conversation
+      className={cn("flex size-full flex-col justify-center", className)}
+    >
+      <ConversationContent
+        className={cn(
+          "mx-auto w-full max-w-(--container-width-lg) gap-8 pt-12",
+          contentClassName,
+        )}
+      >
+        <MessageMetricsProvider messages={messages} isLoading={thread.isLoading}>
         {groupMessages(messages, (group) => {
           if (group.type === "human" || group.type === "assistant") {
             return group.messages.map((msg) => {
@@ -233,11 +242,12 @@ export function MessageList({
                     })
                   : [];
               return (
-                <MessageListItem
-                  key={`${group.id}/${msg.id}`}
-                  message={msg}
-                  isLoading={thread.isLoading}
-                  threadId={threadId}
+                <MessageListItem
+                  key={`${group.id}/${msg.id}`}
+                  fitRowToContent={fitMessageRowsToContent}
+                  message={msg}
+                  isLoading={thread.isLoading}
+                  threadId={threadId}
                   tokenUsageEnabled={tokenUsageEnabled}
                   displaySources={displaySources}
                   extraRehypePlugins={extraRehypePlugins}
diff --git a/frontend-web/src/pages/IframeChatPage.tsx b/frontend-web/src/pages/IframeChatPage.tsx
index e4f7cb31..36d4cc2a 100644
--- a/frontend-web/src/pages/IframeChatPage.tsx
+++ b/frontend-web/src/pages/IframeChatPage.tsx
@@ -313,10 +313,11 @@ export default function IframeChatPage() {
             </div>
           </header>
           <main className="flex min-h-0 max-w-full grow flex-col overflow-hidden">
-            <div className="flex size-full justify-center">
+            <div className="flex size-full min-w-0">
               {!isLandingState && (
                 <MessageList
                   className={cn("size-full", "pt-10")}
+                  contentClassName="mx-0 max-w-full px-3 sm:px-4"
                   threadId={threadId}
                   thread={thread}
                   paddingBottom={messageListPaddingBottom}
@@ -332,7 +333,7 @@ export default function IframeChatPage() {
                   isLandingState && "-translate-y-[calc(50vh-96px)]",
                   isLandingState
                     ? "max-w-(--container-width-md)"
-                    : "max-w-(--container-width-lg)",
+                    : "max-w-full",
                 )}
               >
                 <div className="absolute -top-4 right-0 left-0 z-0">
diff --git a/frontend-web/src/pages/WorkspaceRoutes.tsx b/frontend-web/src/pages/WorkspaceRoutes.tsx
index caf4c509..21a384f4 100644
--- a/frontend-web/src/pages/WorkspaceRoutes.tsx
+++ b/frontend-web/src/pages/WorkspaceRoutes.tsx
@@ -43,6 +43,14 @@ import RoundtablePlanningPage from '@/roundtable-planning/pages/RoundtablePlanni
 import '@/roundtable-planning/styles/roundtable-planning.css';
 import { cn } from '@/lib/utils';
 
+function isInIframe(): boolean {
+  try {
+    return window.self !== window.top;
+  } catch {
+    return true;
+  }
+}
+
 export function WorkspaceLayout({
   children,
   pageSidebarCollapsed,
@@ -116,6 +124,30 @@ export function ChatRuntime({ children }: { children: ReactNode }) {
   );
 }
 
+function NewChatEntryRoute({
+  layoutProps,
+}: {
+  layoutProps: {
+    pageSidebarCollapsed: boolean;
+    pageSidebarHidden: boolean;
+    headerHidden: boolean;
+    compactWorkspaceSidebar: boolean;
+    pageSidebarDark: boolean;
+  };
+}) {
+  if (isInIframe()) {
+    return <Navigate to="/page/workspace/chats_iframe/new" replace />;
+  }
+
+  return (
+    <WorkspaceLayout {...layoutProps}>
+      <ChatRuntime>
+        <ChatPage />
+      </ChatRuntime>
+    </WorkspaceLayout>
+  );
+}
+
 export default function WorkspaceRoutes({
   pageSidebarCollapsed = false,
   pageSidebarHidden = false,
@@ -149,6 +181,10 @@ export default function WorkspaceRoutes({
             </WorkspaceLayout>
           }
         />
+        <Route
+          path="chats/new"
+          element={<NewChatEntryRoute layoutProps={layoutProps} />}
+        />
         <Route
           path="chats/:thread_id"
           element={