diff --git a/AgentCompany-New/src/main/app/startup-recovery.ts b/AgentCompany-New/src/main/app/startup-recovery.ts
new file mode 100644
index 00000000..968df157
--- /dev/null
+++ b/AgentCompany-New/src/main/app/startup-recovery.ts
@@ -0,0 +1,37 @@
+import type { DatabaseSync } from "node:sqlite";
+import { AuditService } from "../services/audit-service";
+
+const INTERRUPTED_MESSAGE = "Interrupted by application shutdown before completion.";
+
+/**
+ * A single app instance executes runs in-process, so any task_run still
+ * `running` at boot was interrupted by a previous shutdown and has no
+ * executor. Marking it failed — together with its in-flight foreground
+ * provider requests — returns the task to the heartbeat, which enqueues a
+ * fresh run within one tick. Background provider requests are left alone:
+ * the provider background worker resumes those from their external id.
+ */
+export function recoverInterruptedWork(db: DatabaseSync): void {
+  const now = new Date().toISOString();
+  const audit = new AuditService(db);
+  const runs = db.prepare("select id, org_id, task_id from task_runs where state = 'running'")
+    .all() as Array<{ id: string; org_id: string; task_id: string }>;
+  for (const run of runs) {
+    db.prepare("update task_runs set state = 'failed', completed_at = ?, error_message = ? where id = ?")
+      .run(now, INTERRUPTED_MESSAGE, run.id);
+    audit.record({
+      orgId: run.org_id,
+      entityType: "task_run",
+      entityId: run.id,
+      actorType: "system",
+      actorId: null,
+      action: "failed",
+      payload: { taskId: run.task_id, reason: "interrupted_by_shutdown" },
+    });
+  }
+  db.prepare(`
+    update provider_requests
+    set state = 'failed', completed_at = ?, error_message = ?
+    where execution_mode = 'foreground' and state in ('pending', 'streaming')
+  `).run(now, INTERRUPTED_MESSAGE);
+}
diff --git a/AgentCompany-New/src/main/index.ts b/AgentCompany-New/src/main/index.ts
index 3e3db4ba..b42b8fc2 100644
--- a/AgentCompany-New/src/main/index.ts
+++ b/AgentCompany-New/src/main/index.ts
@@ -5,6 +5,7 @@ import { DatabaseConnection } from "./database/connection";
 import { createMainWindow } from "./app/create-window";
 import { registerIpcHandlers } from "./app/ipc-handlers";
 import { startProviderBackgroundWorker } from "./app/provider-background-worker";
+import { recoverInterruptedWork } from "./app/startup-recovery";
 import { startTaskQueueWorker } from "./app/task-queue-worker";
 
 const __dirname = dirname(fileURLToPath(import.meta.url));
@@ -17,6 +18,7 @@ if (!hasSingleInstanceLock) {
 app.whenReady().then(() => {
   const profileDir = process.env.AGENTCOMPANY_NEW_PROFILE_DIR ?? join(app.getPath("userData"), "profile");
   const connection = new DatabaseConnection(join(profileDir, "agentcompany.db"));
+  connection.transaction(() => recoverInterruptedWork(connection.db));
   const win = createMainWindow({
     preloadPath: join(__dirname, "../preload/index.js"),
     rendererDist: join(__dirname, "../renderer"),
diff --git a/AgentCompany-New/tests/unit/startup-recovery.test.ts b/AgentCompany-New/tests/unit/startup-recovery.test.ts
new file mode 100644
index 00000000..e254ccc0
--- /dev/null
+++ b/AgentCompany-New/tests/unit/startup-recovery.test.ts
@@ -0,0 +1,90 @@
+import { join } from "node:path";
+import { tmpdir } from "node:os";
+import { randomUUID } from "node:crypto";
+import { describe, expect, test } from "vitest";
+import { DatabaseConnection } from "../../src/main/database/connection";
+import { OnboardingService } from "../../src/main/services/onboarding-service";
+import { TaskExecutionService } from "../../src/main/services/task-execution-service";
+import { claimNextQueuedRun } from "../../src/main/app/task-queue-worker";
+import { recoverInterruptedWork } from "../../src/main/app/startup-recovery";
+import { createId } from "../../src/shared/ids";
+
+describe("startup recovery", () => {
+  test("orphaned running runs fail at boot and the heartbeat re-enqueues the task", () => {
+    const connection = new DatabaseConnection(join(tmpdir(), `ac-recover-${randomUUID()}.db`));
+    const onboarding = new OnboardingService({
+      db: connection.db,
+      saveProviderCredential: ({ orgId, providerId, model }) => {
+        connection.db.prepare("update providers set credential_id = ?, model = ?, enabled = 1 where id = ? and org_id = ?")
+          .run("cred_test", model, providerId, orgId);
+      },
+    });
+
+    let orgId = "";
+    let providerId = "";
+    connection.transaction(() => {
+      const summary = onboarding.bootstrap({
+        companyName: "Acme Operations",
+        companyDescription: "Coordinate agents with auditable approvals.",
+        employeeName: "Dana Lee",
+        workspacePath: "",
+        executionMode: "ai_ceo",
+        autoApproveHires: true,
+        reviewDeliverables: false,
+        goalTitle: "Ship a verified control plane",
+        goalDescription: "Bring the desktop operating loop online.",
+        providerKey: "openai",
+        providerSecret: "test-secret",
+        providerModel: "gpt-5.1",
+      });
+      orgId = summary.orgId;
+      providerId = summary.providerId;
+    });
+
+    // The previous session claimed the run and left in-flight provider requests.
+    const claimed = claimNextQueuedRun(connection);
+    expect(claimed).toBeTruthy();
+    const insertRequest = (id: string, executionMode: string, state: string) => {
+      connection.db.prepare(`
+        insert into provider_requests(
+          id, org_id, provider_id, provider_key, workspace_id, model, prompt_sha256,
+          response_text, raw_response_json, state, error_message, input_char_count,
+          output_char_count, execution_mode, policy_decision, external_response_id,
+          stream_event_count, cancelled_at, created_at, completed_at
+        )
+        values (?, ?, ?, 'openai', null, 'gpt-5.1', 'sha', null, null, ?, null, 10, 0, ?, 'allowed', ?, 0, null, ?, null)
+      `).run(id, orgId, providerId, state, executionMode, executionMode === "background" ? "resp_ext" : null, new Date().toISOString());
+    };
+    const foregroundId = createId("preq");
+    const backgroundId = createId("preq");
+    insertRequest(foregroundId, "foreground", "pending");
+    insertRequest(backgroundId, "background", "pending");
+
+    connection.transaction(() => recoverInterruptedWork(connection.db));
+
+    const run = connection.db.prepare("select state, error_message, completed_at from task_runs where id = ?")
+      .get(claimed!.id) as { state: string; error_message: string; completed_at: string };
+    expect(run.state).toBe("failed");
+    expect(run.error_message).toContain("Interrupted");
+    expect(run.completed_at).toBeTruthy();
+
+    // Foreground orphans fail; background ones stay for the background worker.
+    expect(connection.db.prepare("select state from provider_requests where id = ?").get(foregroundId)).toMatchObject({ state: "failed" });
+    expect(connection.db.prepare("select state from provider_requests where id = ?").get(backgroundId)).toMatchObject({ state: "pending" });
+
+    // The interruption is auditable and the heartbeat immediately retries the task.
+    const audit = connection.db.prepare(
+      "select count(*) as n from audit_events where org_id = ? and entity_type = 'task_run' and action = 'failed'",
+    ).get(orgId) as { n: number };
+    expect(audit.n).toBe(1);
+    const taskExecution = new TaskExecutionService(connection.db);
+    const enqueued = connection.transaction(() => taskExecution.enqueueHeartbeatRuns());
+    expect(enqueued).toHaveLength(1);
+
+    // Recovery is idempotent: a second boot changes nothing.
+    connection.transaction(() => recoverInterruptedWork(connection.db));
+    const failedRuns = connection.db.prepare("select count(*) as n from task_runs where state = 'failed'").get() as { n: number };
+    expect(failedRuns.n).toBe(1);
+    connection.close();
+  });
+});