diff --git a/server/src/__tests__/helpers/maintenance/server-child.ts b/server/src/__tests__/helpers/maintenance/server-child.ts
index 218f7a5bb74..a00a8bd3f58 100644
--- a/server/src/__tests__/helpers/maintenance/server-child.ts
+++ b/server/src/__tests__/helpers/maintenance/server-child.ts
@@ -47,7 +47,7 @@ try {
   const server = await startServer();
   const app = server.server.listeners("request")[0] as unknown as { locals: { paperclipDb: Db } };
   process.send?.({ kind: "ready", port: server.listenPort });
-  process.on("message", async (message: { id: number; command: string; ms?: number; issueUpdate?: { id: string; status: "done" }; publication?: { companyId: string; scopeDigest: string; backupRoot: string; pendingRoot: string } }) => {
+  process.on("message", async (message: { id: number; command: string; ms?: number; issueUpdate?: { id: string; status: "done" }; orphanLease?: { companyId: string }; publication?: { companyId: string; scopeDigest: string; backupRoot: string; pendingRoot: string } }) => {
     try {
       if (message.command === "snapshot" || message.command === "advance" || message.command === "drain" || message.command === "resume" || message.command === "freeze" || message.command === "realtime") {
         if (message.command === "freeze" && bootClock) { clearRealInterval(bootClock); bootClock = realInterval(() => mock.timers.tick(0), 10); }
@@ -60,6 +60,17 @@ try {
         if (message.command === "resume") stopTaskDrain();
         if (fakeClock) mock.timers.tick(0);
         process.send?.({ id: message.id, kind: "snapshot", idle: idleWorkSnapshot(), startup: getStartupRecoveryState(), outgoingHttpRequests, network: network(), now: Date.now() });
+      } else if (message.command === "createOrphanLease") {
+        if (!message.orphanLease) throw new Error("Missing orphan lease fixture");
+        const { environmentLeases } = await import("@paperclipai/db");
+        const { writeEnvironmentCleanup } = await import("../../../services/environment-cleanup-notifications.js");
+        const old = new Date(Date.now() - 6 * 60_000);
+        const companyId = message.orphanLease.companyId;
+        const [lease] = await writeEnvironmentCleanup(app.locals.paperclipDb, tx => tx.insert(environmentLeases).values({
+          companyId, provider: "local", providerLeaseId: null, status: "active", leasePolicy: "ephemeral",
+          acquiredAt: old, lastUsedAt: old, createdAt: old, updatedAt: old,
+        }).returning(), { companyId });
+        process.send?.({ id: message.id, kind: "leaseCreated", leaseId: lease!.id });
       } else if (message.command === "updateIssue") {
         if (!message.issueUpdate) throw new Error("Missing issue update");
         const { issueService } = await import("../../../services/issues.js");
diff --git a/server/src/__tests__/helpers/maintenance/server-harness.ts b/server/src/__tests__/helpers/maintenance/server-harness.ts
index 169ededa625..8f78eba9845 100644
--- a/server/src/__tests__/helpers/maintenance/server-harness.ts
+++ b/server/src/__tests__/helpers/maintenance/server-harness.ts
@@ -93,7 +93,7 @@ export async function startMaintenanceServer(databaseUrl: string, options: { ena
     for (const request of requests.values()) request.reject(error);
     requests.clear();
   });
-  async function request<T>(command: string, payload: { ms?: number; issueUpdate?: { id: string; status: "done" }; publication?: { companyId: string; scopeDigest: string; backupRoot: string; pendingRoot: string } } = {}): Promise<T> {
+  async function request<T>(command: string, payload: { ms?: number; issueUpdate?: { id: string; status: "done" }; orphanLease?: { companyId: string }; publication?: { companyId: string; scopeDigest: string; backupRoot: string; pendingRoot: string } } = {}): Promise<T> {
     const id = ++requestId;
     const result = new Promise<T>((resolve, reject) => requests.set(id, { resolve, reject }));
     child.send({ id, command, ...payload });
@@ -124,6 +124,11 @@ export async function startMaintenanceServer(databaseUrl: string, options: { ena
           return value as T;
         } finally { if (options.clock) await request("freeze"); }
       },
+      async createOrphanLease(companyId: string) {
+        if (options.clock) await request("realtime");
+        try { return await request<{ leaseId: string }>("createOrphanLease", { orphanLease: { companyId } }); }
+        finally { if (options.clock) await request("freeze"); }
+      },
       async updateIssue(issueUpdate: { id: string; status: "done" }) {
         if (options.clock) await request("realtime");
         try { return await request("updateIssue", { issueUpdate }); }
diff --git a/server/src/__tests__/maintenance-server-routes.test.ts b/server/src/__tests__/maintenance-server-routes.test.ts
index 3a21f5d04fd..6980ba70c9a 100644
--- a/server/src/__tests__/maintenance-server-routes.test.ts
+++ b/server/src/__tests__/maintenance-server-routes.test.ts
@@ -1,6 +1,6 @@
 import { createCipheriv, createHash, diffieHellman, generateKeyPairSync, hkdfSync, randomBytes, randomUUID, sign, verify } from "node:crypto";
 import { createServer } from "node:http";
-import { agents, agentApiKeys, agentTaskSessions, authUsers, companies, companyMemberships, connectionGrants, createDb, heartbeatRuns, issues, issueThreadInteractions, toolApplications, toolConnections } from "@paperclipai/db";
+import { agents, agentApiKeys, agentSessionGoalActions, agentTaskSessions, authUsers, companies, companyMemberships, connectionGrants, createDb, heartbeatRuns, issues, issueThreadInteractions, toolApplications, toolConnections } from "@paperclipai/db";
 import { access, mkdir, readdir, utimes, writeFile } from "node:fs/promises";
 import path from "node:path";
 import { setTimeout as delay } from "node:timers/promises";
@@ -65,6 +65,60 @@ describe("assembled maintenance server production wiring", () => {
         repeatedQueries: repeated.length, repeated: receipt(repeated), initialFrames, finalFrames: server.proxy.frames, outgoingHttpRequests: 0 }, null, 2));
     } finally { await server.stop(); }
   }, 150_000);
+  it("isolates a real goal-startup write failure and still registers residual and attention owners", async () => {
+    await clearDatabase();
+    const fixture = createDb(databaseUrl!, { maxConnections: 1 });
+    const companyId = randomUUID(), agentId = randomUUID(), userId = randomUUID(), issueId = randomUUID(), requestId = randomUUID();
+    await fixture.insert(authUsers).values({ id: userId, name: "Goal control owner", email: `${userId}@example.test`, createdAt: new Date(), updatedAt: new Date() });
+    await fixture.insert(companies).values({ id: companyId, name: "Startup failure isolation", issuePrefix: "MFI", defaultResponsibleUserId: userId });
+    await fixture.insert(companyMemberships).values({ companyId, principalType: "user", principalId: userId, status: "active", membershipRole: "member" });
+    await fixture.insert(agents).values({ id: agentId, companyId, name: "Goal owner", adapterType: "codex_local", status: "idle", lifecycleState: "ready" });
+    await fixture.insert(issues).values({ id: issueId, companyId, title: "Retained terminal goal task", status: "done", assigneeAgentId: agentId, responsibleUserId: userId });
+    const [session] = await fixture.insert(agentTaskSessions).values({ companyId, agentId, taskKey: issueId, adapterType: "codex_local" }).returning();
+    const [action] = await fixture.insert(agentSessionGoalActions).values({ companyId, sessionId: session!.id, requestId,
+      action: "clear", payloadJson: { requestId, action: "clear" }, status: "pending" }).returning();
+    await fixture.$client.unsafe(`create or replace function maintenance_fail_goal_startup() returns trigger language plpgsql as $$begin
+      if new.reason = 'goal_control' then raise exception 'maintenance_goal_startup_injected'; end if; return new; end$$`);
+    await fixture.$client.unsafe(`create trigger maintenance_fail_goal_startup before insert on agent_wakeup_requests for each row execute function maintenance_fail_goal_startup()`);
+    let server: Awaited<ReturnType<typeof startMaintenanceServer>> | undefined;
+    try {
+      server = await startMaintenanceServer(databaseUrl!, { clock: true });
+      await settleClock(server);
+      expect((await server.snapshot()).startup.phase).toBe("ready");
+      expect(server.output).toContain("maintenance_goal_startup_injected");
+      const [retained] = await fixture.$client`select status from agent_session_goal_actions where id=${action!.id}`;
+      expect(retained!.status).toBe("pending");
+      const [failedWake] = await fixture.$client`select count(*)::integer as count from agent_wakeup_requests where reason='goal_control'`;
+      expect(failedWake!.count).toBe(0);
+      const start = (await server.snapshot()).now;
+      const { leaseId } = await server.createOrphanLease(companyId);
+      await server.advance(1_000); await settleClock(server);
+      const [lease] = await fixture.$client`select status, cleanup_status, provider, provider_lease_id from environment_leases where id=${leaseId}`;
+      expect(lease).toMatchObject({ status: "expired", cleanup_status: "success", provider: "local", provider_lease_id: null });
+      const elapsedClockMs = (await server.snapshot()).now - start;
+      expect(elapsedClockMs).toBeLessThan(30_000);
+      await fixture.$client.unsafe(`create or replace function maintenance_age_isolation_attention() returns trigger language plpgsql as $$begin
+        if new.title = 'Attention after goal failure' then new.updated_at = now() - interval '91 days'; end if; return new; end$$`);
+      await fixture.$client.unsafe(`create trigger maintenance_age_isolation_attention before insert on issue_thread_interactions for each row execute function maintenance_age_isolation_attention()`);
+      const issue = await server.api<{ id: string }>("POST", `/companies/${companyId}/issues`, { title: "Independent attention owner", status: "todo" });
+      const card = await server.api<{ id: string }>("POST", `/issues/${issue.id}/interactions`, { kind: "request_confirmation", title: "Attention after goal failure",
+        resolverPolicy: "human_only", continuationPolicy: "none", payload: { version: 1, prompt: "Choose a color?" } });
+      await server.advance(1_000); await settleClock(server);
+      const [archived] = await fixture.$client`select archived_reason, archived_at is not null as archived from decision_retention where source_id=${card.id}`;
+      expect(archived).toMatchObject({ archived_reason: "idle_ttl", archived: true });
+      await writeFile(path.join(server.directory, "startup-failure-measurement.json"), JSON.stringify({ phase: "actual-goal-startup-failure-isolation",
+        companyId, actionId: action!.id, retained, failedWake, leaseId, lease, elapsedClockMs, archived, frames: server.proxy.frames,
+        boundary: "fixture-only conditional goal_control INSERT failure; actual native classification untouched; actual environment cleanup ingress and ordinary attention HTTP producer",
+      }, null, 2));
+    } finally {
+      await fixture.$client.unsafe("drop trigger if exists maintenance_fail_goal_startup on agent_wakeup_requests").catch(() => {});
+      await fixture.$client.unsafe("drop function if exists maintenance_fail_goal_startup()").catch(() => {});
+      await fixture.$client.unsafe("drop trigger if exists maintenance_age_isolation_attention on issue_thread_interactions").catch(() => {});
+      await fixture.$client.unsafe("drop function if exists maintenance_age_isolation_attention()").catch(() => {});
+      await server?.stop(); await fixture.$client.end();
+    }
+  }, 150_000);
+
   it("exposes readiness while real deferred housekeeping is held and settles its work after release", async () => {
     await clearDatabase();
     const fixture = createDb(databaseUrl!, { maxConnections: 1 });