diff --git a/apps/rowboat/app/projects/[projectId]/playground/app.tsx b/apps/rowboat/app/projects/[projectId]/playground/app.tsx
index 7a0e94a1..fc920276 100644
--- a/apps/rowboat/app/projects/[projectId]/playground/app.tsx
+++ b/apps/rowboat/app/projects/[projectId]/playground/app.tsx
@@ -11,7 +11,7 @@ import { apiV1 } from "rowboat-shared";
 import { TestProfile } from "@/app/lib/types/testing_types";
 import { WithStringId } from "@/app/lib/types/types";
 import { ProfileSelector } from "@/app/projects/[projectId]/test/[[...slug]]/components/selectors/profile-selector";
-import { CheckIcon, CopyIcon, PlusIcon, UserIcon, InfoIcon } from "lucide-react";
+import { CheckIcon, CopyIcon, PlusIcon, UserIcon, InfoIcon, BugIcon, BugOffIcon } from "lucide-react";
 import { USE_TESTING_FEATURE } from "@/app/lib/feature_flags";
 import { clsx } from "clsx";
 
@@ -39,6 +39,7 @@ export function App({
     const [counter, setCounter] = useState<number>(0);
     const [testProfile, setTestProfile] = useState<WithStringId<z.infer<typeof TestProfile>> | null>(null);
     const [systemMessage, setSystemMessage] = useState<string>(defaultSystemMessage);
+    const [showDebugMessages, setShowDebugMessages] = useState<boolean>(true);
     const [chat, setChat] = useState<z.infer<typeof PlaygroundChat>>({
         projectId,
         createdAt: new Date().toISOString(),
@@ -116,6 +117,20 @@ export function App({
                         >
                             <PlusIcon className="w-4 h-4" />
                         </Button>
+                        <Button
+                            variant="primary"
+                            size="sm"
+                            onClick={() => setShowDebugMessages(!showDebugMessages)}
+                            className={showDebugMessages ? "bg-blue-50 text-blue-700 hover:bg-blue-100" : "bg-gray-50 text-gray-500 hover:bg-gray-100"}
+                            showHoverContent={true}
+                            hoverContent={showDebugMessages ? "Hide debug messages" : "Show debug messages"}
+                        >
+                            {showDebugMessages ? (
+                                <BugIcon className="w-4 h-4" />
+                            ) : (
+                                <BugOffIcon className="w-4 h-4" />
+                            )}
+                        </Button>
                     </div>
                 }
                 rightActions={
@@ -169,6 +184,7 @@ export function App({
                         mcpServerUrls={mcpServerUrls}
                         toolWebhookUrl={toolWebhookUrl}
                         onCopyClick={(fn) => { getCopyContentRef.current = fn; }}
+                        showDebugMessages={showDebugMessages}
                     />
                 </div>
             </Panel>
diff --git a/apps/rowboat/app/projects/[projectId]/playground/components/chat.tsx b/apps/rowboat/app/projects/[projectId]/playground/components/chat.tsx
index 14347e08..16d07fb8 100644
--- a/apps/rowboat/app/projects/[projectId]/playground/components/chat.tsx
+++ b/apps/rowboat/app/projects/[projectId]/playground/components/chat.tsx
@@ -28,6 +28,7 @@ export function Chat({
     mcpServerUrls,
     toolWebhookUrl,
     onCopyClick,
+    showDebugMessages = true,
 }: {
     chat: z.infer<typeof PlaygroundChat>;
     projectId: string;
@@ -40,6 +41,7 @@ export function Chat({
     mcpServerUrls: Array<z.infer<typeof MCPServer>>;
     toolWebhookUrl: string;
     onCopyClick: (fn: () => string) => void;
+    showDebugMessages?: boolean;
 }) {
     const [messages, setMessages] = useState<z.infer<typeof apiV1.ChatMessage>[]>(chat.messages);
     const [loadingAssistantResponse, setLoadingAssistantResponse] = useState<boolean>(false);
@@ -285,6 +287,7 @@ export function Chat({
                     systemMessage={systemMessage}
                     onSystemMessageChange={onSystemMessageChange}
                     showSystemMessage={false}
+                    showDebugMessages={showDebugMessages}
                 />
             </div>
         </div>
diff --git a/apps/rowboat/app/projects/[projectId]/playground/components/messages.tsx b/apps/rowboat/app/projects/[projectId]/playground/components/messages.tsx
index af6530a9..693cc11b 100644
--- a/apps/rowboat/app/projects/[projectId]/playground/components/messages.tsx
+++ b/apps/rowboat/app/projects/[projectId]/playground/components/messages.tsx
@@ -35,12 +35,15 @@ function InternalAssistantMessage({ content, sender, latency, delta }: { content
 
     // Show plus icon and duration
     const deltaDisplay = (
-        <span className="inline-flex items-center gap-1 text-gray-400 dark:text-gray-500">
-            <PlusIcon size={12} />
-            {Math.round(delta / 1000)}s
+        <span className="inline-flex items-center text-gray-400 dark:text-gray-500">
+            +{Math.round(delta / 1000)}s
         </span>
     );
 
+    // Get first line preview
+    const firstLine = content.split('\n')[0].trim();
+    const preview = firstLine.length > 50 ? firstLine.substring(0, 50) + '...' : firstLine;
+
     return (
         <div className="self-start flex flex-col gap-1 my-5">
             <div className="text-gray-500 dark:text-gray-400 text-xs pl-1">
@@ -49,15 +52,20 @@ function InternalAssistantMessage({ content, sender, latency, delta }: { content
             <div className={expanded ? 'max-w-[85%] inline-block' : 'inline-block'}>
                 <div className={expanded
                   ? 'bg-gray-50 dark:bg-zinc-800 px-4 py-2.5 rounded-2xl rounded-bl-lg text-sm leading-relaxed text-gray-700 dark:text-gray-200 border-none shadow-sm animate-slideUpAndFade flex flex-col items-stretch'
-                  : 'bg-gray-50 dark:bg-zinc-800 px-4 py-0.5 rounded-2xl rounded-bl-lg text-sm leading-relaxed text-gray-700 dark:text-gray-200 border-none shadow-sm animate-slideUpAndFade w-fit'}>
+                  : 'bg-gray-50 dark:bg-zinc-800 px-4 py-2.5 rounded-2xl rounded-bl-lg text-sm leading-relaxed text-gray-700 dark:text-gray-200 border-none shadow-sm animate-slideUpAndFade w-fit'}>
                     {!expanded ? (
-                        <div className="flex justify-between items-center gap-6 mt-2">
-                            <button className="flex items-center gap-1 text-xs text-gray-600 dark:text-gray-300 hover:underline self-start" onClick={() => setExpanded(true)}>
-                                <ChevronDownIcon size={16} />
-                                Show internal message
-                            </button>
-                            <div className="text-right text-xs">
-                                {deltaDisplay}
+                        <div className="flex flex-col gap-2">
+                            <div className="text-gray-700 dark:text-gray-200">
+                                {preview}
+                            </div>
+                            <div className="flex justify-between items-center gap-6">
+                                <button className="flex items-center gap-1 text-xs text-gray-600 dark:text-gray-300 hover:underline self-start" onClick={() => setExpanded(true)}>
+                                    <ChevronDownIcon size={16} />
+                                    Show internal message
+                                </button>
+                                <div className="text-right text-xs">
+                                    {deltaDisplay}
+                                </div>
                             </div>
                         </div>
                     ) : (
@@ -207,9 +215,8 @@ function TransferToAgentToolCall({
         return <></>;
     }
     const deltaDisplay = (
-        <span className="inline-flex items-center gap-1 text-gray-400 dark:text-gray-500">
-            <PlusIcon size={12} />
-            {Math.round(delta / 1000)}s
+        <span className="inline-flex items-center text-gray-400 dark:text-gray-500">
+            +{Math.round(delta / 1000)}s
         </span>
     );
     return (
@@ -333,6 +340,7 @@ export function Messages({
     systemMessage,
     onSystemMessageChange,
     showSystemMessage,
+    showDebugMessages = true,
 }: {
     projectId: string;
     messages: z.infer<typeof apiV1.ChatMessage>[];
@@ -343,6 +351,7 @@ export function Messages({
     systemMessage: string | undefined;
     onSystemMessageChange: (message: string) => void;
     showSystemMessage: boolean;
+    showDebugMessages?: boolean;
 }) {
     const messagesEndRef = useRef<HTMLDivElement>(null);
     let lastUserMessageTimestamp = 0;
@@ -363,6 +372,12 @@ export function Messages({
             // Helper: is this message a transfer pill or internal message?
             const isTransferPill = 'tool_calls' in message && message.tool_calls.some(tc => tc.function.name.startsWith('transfer_to_'));
             const isInternal = message.agenticResponseType === 'internal';
+            
+            // Skip internal messages and transfer pills if debug mode is off
+            if (!showDebugMessages && (isTransferPill || isInternal)) {
+                return null;
+            }
+
             if (isTransferPill || isInternal) {
                 // Find previous message that is either a transfer pill or internal message
                 let delta = latency;
@@ -442,11 +457,17 @@ export function Messages({
     return (
         <div className="max-w-[768px] mx-auto">
             <div className="flex flex-col">
-                {messages.map((message, index) => (
-                    <div key={index}>
-                        {renderMessage(message, index)}
-                    </div>
-                ))}
+                {messages.map((message, index) => {
+                    const renderedMessage = renderMessage(message, index);
+                    if (renderedMessage) {
+                        return (
+                            <div key={index}>
+                                {renderedMessage}
+                            </div>
+                        );
+                    }
+                    return null;
+                })}
                 {loadingAssistantResponse && <AssistantMessageLoading />}
             </div>
             <div ref={messagesEndRef} />