diff --git a/server/src/__tests__/environment-run-lease-ownership.test.ts b/server/src/__tests__/environment-run-lease-ownership.test.ts
index a8a666a0ebc..669293cf660 100644
--- a/server/src/__tests__/environment-run-lease-ownership.test.ts
+++ b/server/src/__tests__/environment-run-lease-ownership.test.ts
@@ -1,6 +1,6 @@
 import { spawn } from "node:child_process";
 import { randomUUID } from "node:crypto";
-import { eq } from "drizzle-orm";
+import { eq, sql } from "drizzle-orm";
 import { afterAll, afterEach, beforeAll, describe, expect, it, vi } from "vitest";
 import {
   agents,
@@ -257,6 +257,17 @@ suite("environment_run_lease_active on the shared ownership path", () => {
   });
 
   describe("leases saved before holders were stamped", () => {
+    it("dates the first cleanup attempt as a top-level key even for a scalar metadata root", async () => {
+      const runId = await run("failed");
+      const id = randomUUID();
+      await db.insert(environmentLeases).values({ id, companyId, heartbeatRunId: runId, status: "active",
+        metadata: sql`'["provider-wrote-an-array"]'::jsonb` });
+      await runOwnershipReconciliationPass(db, { state: createOwnershipReportState() });
+      const settled = await row(id);
+      expect(settled.status).toBe("pending_cleanup");
+      expect(typeof settled.metadata?.pendingCleanupRecoveredAtMs).toBe("number");
+    });
+
     it("keeps the run fact alone for one release on a single-host server", async () => {
       const runId = await run("failed");
       const leaseId = await lease(runId, null);
diff --git a/server/src/services/environment-run-lease-settlement.ts b/server/src/services/environment-run-lease-settlement.ts
index fb1c79a471e..f6020a1ed6f 100644
--- a/server/src/services/environment-run-lease-settlement.ts
+++ b/server/src/services/environment-run-lease-settlement.ts
@@ -2,6 +2,7 @@ import { and, eq, inArray, ne, notInArray, or, sql } from "drizzle-orm";
 import { environmentLeases, environments, heartbeatRuns, nativeRunFinalizations, nativeRunResults, type Db } from "@paperclipai/db";
 import { currentControllerBootId } from "./controller-process-identity.js";
 import { writeEnvironmentCleanup } from "./environment-cleanup-notifications.js";
+import { pendingCleanupMetadataObjectSql } from "./environment-cleanup-state.js";
 import { readEnvironmentLeaseController } from "./environment-lease-controller.js";
 import { allowLegacyShutdownWorkspaceCleanup } from "./legacy-shutdown-workspace-settlement.js";
 import { nativeWorkspaceExportPendingForLease } from "./native-runtime/native-workspace-finalization-state.js";
@@ -77,7 +78,8 @@ export async function settleEnvironmentRunLease(db: Db, record: InProgressRecord
     const flipped = await writeEnvironmentCleanup(tx, write => write.update(environmentLeases)
       .set({ status: "pending_cleanup", failureReason: ORPHANED_RUN_LEASE_FAILURE_REASON,
         // When the first cleanup attempt became due (the row keeps updatedAt).
-        metadata: sql`coalesce(${environmentLeases.metadata}, '{}'::jsonb) || ${JSON.stringify({
+        // A scalar or array root reads as an empty object, so the key is top level.
+        metadata: sql`${pendingCleanupMetadataObjectSql()} || ${JSON.stringify({
           pendingCleanupRecoveredAtMs: context.now.getTime() })}::jsonb` })
       .where(and(eq(environmentLeases.id, lease.id), eq(environmentLeases.status, "active"),
         eq(environmentLeases.heartbeatRunId, runId),