diff --git a/apps/twig/src/renderer/features/sessions/components/SessionView.tsx b/apps/twig/src/renderer/features/sessions/components/SessionView.tsx
index 53b6869e6..3fcc1ddef 100644
--- a/apps/twig/src/renderer/features/sessions/components/SessionView.tsx
+++ b/apps/twig/src/renderer/features/sessions/components/SessionView.tsx
@@ -42,6 +42,7 @@ interface SessionViewProps {
   onCancelPrompt: () => void;
   repoPath?: string | null;
   hasError?: boolean;
+  errorTitle?: string;
   errorMessage?: string;
   onRetry?: () => void;
   onDelete?: () => void;
@@ -62,6 +63,7 @@ export function SessionView({
   onCancelPrompt,
   repoPath,
   hasError = false,
+  errorTitle,
   errorMessage = DEFAULT_ERROR_MESSAGE,
   onRetry,
   onDelete,
@@ -380,11 +382,16 @@ export function SessionView({
                   className="absolute inset-0 bg-gray-1"
                 >
                   <Warning size={32} weight="duotone" color="var(--red-9)" />
+                  {errorTitle && (
+                    <Text size="3" weight="bold" align="center" color="red">
+                      {errorTitle}
+                    </Text>
+                  )}
                   <Text
-                    size="3"
-                    weight="medium"
+                    size={errorTitle ? "2" : "3"}
+                    weight={errorTitle ? "regular" : "medium"}
                     align="center"
-                    color="red"
+                    color={errorTitle ? "gray" : "red"}
                     className="max-w-md px-4"
                   >
                     {errorMessage}
diff --git a/apps/twig/src/renderer/features/sessions/service/service.ts b/apps/twig/src/renderer/features/sessions/service/service.ts
index cfef40d32..e0f46c596 100644
--- a/apps/twig/src/renderer/features/sessions/service/service.ts
+++ b/apps/twig/src/renderer/features/sessions/service/service.ts
@@ -268,7 +268,8 @@ export class SessionService {
       const taskRunId = latestRun?.id ?? `error-${taskId}`;
       const session = this.createBaseSession(taskRunId, taskId, taskTitle);
       session.status = "error";
-      session.errorMessage = `Failed to connect to the agent: ${message}`;
+      session.errorTitle = "Failed to connect";
+      session.errorMessage = message;
 
       if (latestRun?.log_url) {
         try {
@@ -487,9 +488,11 @@ export class SessionService {
     taskRunId: string,
     taskTitle: string,
     errorMessage: string,
+    errorTitle?: string,
   ): void {
     const session = this.createBaseSession(taskRunId, taskId, taskTitle);
     session.status = "error";
+    session.errorTitle = errorTitle;
     session.errorMessage = errorMessage;
     sessionStoreSetters.setSession(session);
   }
@@ -1365,8 +1368,6 @@ export class SessionService {
     if (session) {
       await this.teardownSession(session.taskRunId);
     }
-    // Clear from connecting tasks as well
-    this.connectingTasks.delete(taskId);
   }
 
   /**
diff --git a/apps/twig/src/renderer/features/sessions/stores/sessionStore.ts b/apps/twig/src/renderer/features/sessions/stores/sessionStore.ts
index eca6501f9..5a30b0df5 100644
--- a/apps/twig/src/renderer/features/sessions/stores/sessionStore.ts
+++ b/apps/twig/src/renderer/features/sessions/stores/sessionStore.ts
@@ -36,6 +36,7 @@ export interface AgentSession {
   events: AcpMessage[];
   startedAt: number;
   status: "connecting" | "connected" | "disconnected" | "error";
+  errorTitle?: string;
   errorMessage?: string;
   isPromptPending: boolean;
   logUrl?: string;
diff --git a/apps/twig/src/renderer/features/task-detail/components/TaskLogsPanel.tsx b/apps/twig/src/renderer/features/task-detail/components/TaskLogsPanel.tsx
index cb94140b8..48c52146c 100644
--- a/apps/twig/src/renderer/features/task-detail/components/TaskLogsPanel.tsx
+++ b/apps/twig/src/renderer/features/task-detail/components/TaskLogsPanel.tsx
@@ -69,6 +69,7 @@ export function TaskLogsPanel({ taskId, task }: TaskLogsPanelProps) {
   const isRunning =
     session?.status === "connected" || session?.status === "connecting";
   const hasError = session?.status === "error";
+  const errorTitle = session?.errorTitle;
   const errorMessage = session?.errorMessage;
 
   const events = session?.events ?? [];
@@ -236,8 +237,7 @@ export function TaskLogsPanel({ taskId, task }: TaskLogsPanelProps) {
   const handleRetry = useCallback(async () => {
     if (!repoPath) return;
     await getSessionService().clearSessionError(taskId);
-    getSessionService().connectToTask({ task, repoPath });
-  }, [taskId, repoPath, task]);
+  }, [taskId, repoPath]);
 
   const handleDelete = useCallback(() => {
     const hasWorktree = workspace?.mode === "worktree";
@@ -322,6 +322,7 @@ export function TaskLogsPanel({ taskId, task }: TaskLogsPanelProps) {
               onCancelPrompt={handleCancelPrompt}
               repoPath={repoPath}
               hasError={isCloud ? false : hasError}
+              errorTitle={isCloud ? undefined : errorTitle}
               errorMessage={isCloud ? undefined : errorMessage}
               onRetry={handleRetry}
               onDelete={handleDelete}