diff --git a/.changeset/compact-session-start-recovery.md b/.changeset/compact-session-start-recovery.md
new file mode 100644
index 0000000000..55b04bffd5
--- /dev/null
+++ b/.changeset/compact-session-start-recovery.md
@@ -0,0 +1,5 @@
+---
+"@roomote/web": patch
+---
+
+Show Session start failures in a compact inline row with a clear Retry action instead of an oversized error panel and technical transport message.
diff --git a/apps/web/src/app/(authenticated)/home/Home.client.test.tsx b/apps/web/src/app/(authenticated)/home/Home.client.test.tsx
index 5454389105..f799fc5aed 100644
--- a/apps/web/src/app/(authenticated)/home/Home.client.test.tsx
+++ b/apps/web/src/app/(authenticated)/home/Home.client.test.tsx
@@ -902,7 +902,9 @@ describe('Home', () => {
 
   it('reuses the client conversation identity after an ambiguous start failure', async () => {
     mockStartFastSession
-      .mockRejectedValueOnce(new Error('Connection lost'))
+      .mockRejectedValueOnce(
+        new Error('Stream closed before head was received'),
+      )
       .mockResolvedValueOnce({
         sessionId: '11111111-1111-4111-8111-111111111111',
         fastConversationId: '22222222-2222-4222-8222-222222222222',
@@ -911,8 +913,11 @@ describe('Home', () => {
 
     fireEvent.click(screen.getByRole('button', { name: 'Submit prompt' }));
     expect(await screen.findByRole('alert')).toHaveTextContent(
-      'Connection lost',
+      'Couldn’t start this session.',
     );
+    expect(
+      screen.queryByText('Stream closed before head was received'),
+    ).not.toBeInTheDocument();
     expect(screen.queryByRole('dialog')).not.toBeInTheDocument();
     // Editing the composer after the failure must not change what Retry sends.
     fireEvent.change(screen.getByRole('textbox', { name: 'Task prompt' }), {
@@ -938,7 +943,7 @@ describe('Home', () => {
 
     fireEvent.click(screen.getByRole('button', { name: 'Submit prompt' }));
     expect(await screen.findByRole('alert')).toHaveTextContent(
-      'Connection lost',
+      'Couldn’t start this session.',
     );
     submittedPromptText = 'Corrected prompt';
     fireEvent.click(screen.getByRole('button', { name: 'Submit prompt' }));
diff --git a/apps/web/src/components/tasks/NewTaskForm.tsx b/apps/web/src/components/tasks/NewTaskForm.tsx
index e51ccb04ff..ba6aee9627 100644
--- a/apps/web/src/components/tasks/NewTaskForm.tsx
+++ b/apps/web/src/components/tasks/NewTaskForm.tsx
@@ -23,10 +23,10 @@ import {
   TaskPromptInput,
 } from '@/components/tasks';
 import {
+  AlertCircle,
   BasicTooltip,
   Button,
   HatGlasses,
-  RetryableLoadError,
 } from '@/components/system';
 
 const DEFAULT_PROMPT_PLACEHOLDER = 'What do you want to do?';
@@ -269,13 +269,23 @@ export function NewTaskForm({
         }
       />
       {fastSessionError ? (
-        <div role="alert">
-          <RetryableLoadError
-            className="mt-3 p-4 md:p-4 [&_[data-slot=empty-icon]]:mb-0"
-            message={fastSessionError.message}
-            isRetrying={isFastSessionPending}
-            onRetry={() => void retryFastSession()}
+        <div role="alert" className="flex items-center gap-2 px-3 py-2 text-sm">
+          <AlertCircle
+            aria-hidden="true"
+            className="text-destructive size-4 shrink-0"
           />
+          <p className="text-muted-foreground min-w-0 flex-1">
+            Couldn’t start this session.
+          </p>
+          <Button
+            type="button"
+            variant="ghost"
+            size="sm"
+            disabled={isFastSessionPending}
+            onClick={() => void retryFastSession()}
+          >
+            Retry
+          </Button>
         </div>
       ) : null}
     </div>