diff --git a/apps/code/src/renderer/features/sessions/service/service.test.ts b/apps/code/src/renderer/features/sessions/service/service.test.ts
index 1408ed18e..55c4239b6 100644
--- a/apps/code/src/renderer/features/sessions/service/service.test.ts
+++ b/apps/code/src/renderer/features/sessions/service/service.test.ts
@@ -566,6 +566,148 @@ describe("SessionService", () => {
         }),
       );
     });
+
+    describe("auto-retry on connect failure", () => {
+      const setupFailingConnect = () => {
+        const createTaskRun = vi
+          .fn()
+          .mockRejectedValue(new Error("Internal error"));
+        mockBuildAuthenticatedClient.mockReturnValue({
+          ...mockAuthenticatedClient,
+          createTaskRun,
+          appendTaskRunLog: vi.fn(),
+        });
+        return { createTaskRun };
+      };
+
+      it("parks the session in 'connecting' and auto-retries via clearSessionError", async () => {
+        vi.useFakeTimers();
+        try {
+          setupFailingConnect();
+          const service = getSessionService();
+          const clearSpy = vi
+            .spyOn(service, "clearSessionError")
+            .mockResolvedValue(undefined);
+
+          const promise = service.connectToTask({
+            task: createMockTask(),
+            repoPath: "/repo",
+          });
+
+          await vi.advanceTimersByTimeAsync(0);
+          expect(mockSessionStoreSetters.setSession).toHaveBeenCalledWith(
+            expect.objectContaining({ status: "connecting" }),
+          );
+
+          await vi.advanceTimersByTimeAsync(10_000);
+          await promise;
+
+          expect(clearSpy).toHaveBeenCalledTimes(1);
+          expect(clearSpy).toHaveBeenCalledWith("task-123", "/repo");
+          expect(mockSessionStoreSetters.setSession).not.toHaveBeenCalledWith(
+            expect.objectContaining({ status: "error" }),
+          );
+        } finally {
+          vi.useRealTimers();
+        }
+      });
+
+      it("flips to error after both auto-retries fail", async () => {
+        vi.useFakeTimers();
+        try {
+          setupFailingConnect();
+          const service = getSessionService();
+          const clearSpy = vi
+            .spyOn(service, "clearSessionError")
+            .mockRejectedValue(new Error("retry failed"));
+          mockSessionStoreSetters.getSessionByTaskId.mockReturnValue({
+            taskRunId: "error-task-123",
+            taskId: "task-123",
+          });
+
+          const promise = service.connectToTask({
+            task: createMockTask(),
+            repoPath: "/repo",
+          });
+
+          await vi.advanceTimersByTimeAsync(25_000);
+          await promise;
+
+          expect(clearSpy).toHaveBeenCalledTimes(2);
+          expect(mockSessionStoreSetters.updateSession).toHaveBeenCalledWith(
+            "error-task-123",
+            expect.objectContaining({
+              status: "error",
+              errorTitle: "Failed to connect",
+              errorMessage: "retry failed",
+            }),
+          );
+        } finally {
+          vi.useRealTimers();
+        }
+      });
+
+      it("stops retrying and sets disconnected when device goes offline", async () => {
+        vi.useFakeTimers();
+        try {
+          setupFailingConnect();
+          const service = getSessionService();
+          const clearSpy = vi
+            .spyOn(service, "clearSessionError")
+            .mockResolvedValue(undefined);
+          mockSessionStoreSetters.getSessionByTaskId.mockReturnValue({
+            taskRunId: "error-task-123",
+            taskId: "task-123",
+          });
+
+          const promise = service.connectToTask({
+            task: createMockTask(),
+            repoPath: "/repo",
+          });
+
+          await vi.advanceTimersByTimeAsync(0);
+          mockGetIsOnline.mockReturnValue(false);
+          await vi.advanceTimersByTimeAsync(10_000);
+          await promise;
+
+          expect(clearSpy).not.toHaveBeenCalled();
+          expect(mockSessionStoreSetters.updateSession).toHaveBeenCalledWith(
+            "error-task-123",
+            expect.objectContaining({
+              status: "disconnected",
+              errorMessage: expect.stringContaining("No internet connection"),
+            }),
+          );
+        } finally {
+          vi.useRealTimers();
+        }
+      });
+
+      it("skips final update when session was dismissed during retry gap", async () => {
+        vi.useFakeTimers();
+        try {
+          setupFailingConnect();
+          const service = getSessionService();
+          const clearSpy = vi
+            .spyOn(service, "clearSessionError")
+            .mockRejectedValue(new Error("retry failed"));
+          mockSessionStoreSetters.getSessionByTaskId.mockReturnValue(undefined);
+
+          const promise = service.connectToTask({
+            task: createMockTask(),
+            repoPath: "/repo",
+          });
+
+          await vi.advanceTimersByTimeAsync(25_000);
+          await promise;
+
+          expect(clearSpy).toHaveBeenCalled();
+          expect(mockSessionStoreSetters.updateSession).not.toHaveBeenCalled();
+        } finally {
+          vi.useRealTimers();
+        }
+      });
+    });
   });
 
   describe("disconnectFromTask", () => {
diff --git a/apps/code/src/renderer/features/sessions/service/service.ts b/apps/code/src/renderer/features/sessions/service/service.ts
index 4636440a2..f7ac2facd 100644
--- a/apps/code/src/renderer/features/sessions/service/service.ts
+++ b/apps/code/src/renderer/features/sessions/service/service.ts
@@ -93,6 +93,8 @@ const LOCAL_SESSION_RECOVERY_MESSAGE =
 const LOCAL_SESSION_RECOVERY_FAILED_MESSAGE =
   "Connecting to to the agent has been lost. Retry, or start a new session.";
 const GITHUB_AUTHORIZATION_REQUIRED_CODE = "github_authorization_required";
+const AUTO_RETRY_MAX_ATTEMPTS = 2;
+const AUTO_RETRY_DELAY_MS = 10_000;
 
 class GitHubAuthorizationRequiredForCloudHandoffError extends Error {
   constructor(
@@ -443,13 +445,9 @@ export class SessionService {
 
       const taskRunId = latestRun?.id ?? `error-${taskId}`;
       const session = this.createBaseSession(taskRunId, taskId, taskTitle);
-      session.status = "error";
-      session.errorTitle = "Failed to connect";
-      session.errorMessage = message;
       if (initialPrompt?.length) {
         session.initialPrompt = initialPrompt;
       }
-
       if (latestRun?.log_url) {
         try {
           const { rawEntries } = await this.fetchSessionLogs(
@@ -463,7 +461,60 @@ export class SessionService {
         }
       }
 
+      const shouldAutoRetry = getIsOnline();
+      session.status = shouldAutoRetry ? "connecting" : "error";
+      if (!shouldAutoRetry) {
+        session.errorTitle = "Failed to connect";
+        session.errorMessage = message;
+      }
       sessionStoreSetters.setSession(session);
+
+      if (!shouldAutoRetry) return;
+
+      let lastRetryMessage = message;
+      let wentOffline = false;
+      for (let attempt = 1; attempt <= AUTO_RETRY_MAX_ATTEMPTS; attempt++) {
+        log.warn("Auto-retrying failed connection", {
+          taskId,
+          attempt,
+          delayMs: AUTO_RETRY_DELAY_MS,
+        });
+        await new Promise((resolve) =>
+          setTimeout(resolve, AUTO_RETRY_DELAY_MS),
+        );
+        if (!getIsOnline()) {
+          log.warn("Skipping retry — device went offline", {
+            taskId,
+            attempt,
+          });
+          wentOffline = true;
+          break;
+        }
+        try {
+          await this.clearSessionError(taskId, repoPath);
+          return;
+        } catch (retryError) {
+          lastRetryMessage =
+            retryError instanceof Error
+              ? retryError.message
+              : String(retryError);
+          log.error("Auto-retry via clearSessionError failed", {
+            taskId,
+            attempt,
+            error: lastRetryMessage,
+          });
+        }
+      }
+
+      const currentSession = sessionStoreSetters.getSessionByTaskId(taskId);
+      if (!currentSession) return;
+      sessionStoreSetters.updateSession(currentSession.taskRunId, {
+        status: wentOffline ? "disconnected" : "error",
+        errorTitle: wentOffline ? undefined : "Failed to connect",
+        errorMessage: wentOffline
+          ? "No internet connection. Connect when you're back online."
+          : lastRetryMessage || message,
+      });
     }
   }