diff --git a/tests/runner-e2e/chat-catalog-domains/privileged-cli-observer.test.ts b/tests/runner-e2e/chat-catalog-domains/privileged-cli-observer.test.ts
new file mode 100644
index 00000000000..e1cbd89f908
--- /dev/null
+++ b/tests/runner-e2e/chat-catalog-domains/privileged-cli-observer.test.ts
@@ -0,0 +1,68 @@
+import { afterEach, expect, it, vi } from "vitest";
+import { observeInternal } from "./internal-support.js";
+import { runOwnedCli } from "./privileged-cli-support.js";
+import { privilegedCliCases } from "./privileged-cli.js";
+import type { ChatCatalogContext } from "../chat-catalog-contract.js";
+vi.mock("./internal-definition.js", () => ({ fixtureWorker: vi.fn() }));
+vi.mock("./internal-support.js", async original => ({
+  ...await original<typeof import("./internal-support.js")>(), observeInternal: vi.fn(),
+}));
+vi.mock("./privileged-cli-support.js", async original => ({
+  ...await original<typeof import("./privileged-cli-support.js")>(), runOwnedCli: vi.fn(),
+}));
+afterEach(() => { vi.useRealTimers(); vi.restoreAllMocks(); vi.clearAllMocks(); });
+const start = 50_000;
+function fixture(scenario: string) {
+  vi.useFakeTimers(); vi.setSystemTime(start);
+  let completesAt = start + 160_000, status = "succeeded", noWork = false;
+  const ctx = { observationDeadlineAt: start + 390_000,
+    issue: () => ({ conversationState: Date.now() >= completesAt ? "waiting" : "running" }),
+    input: { execution: { id: `chat-features.runner-opencode.local.${scenario}` },
+      fixtures: { company: { id: "owned-company" } }, api: { baseURL: "http://fixture.test" } },
+  } as unknown as ChatCatalogContext;
+  vi.mocked(observeInternal).mockImplementation(async () => ({
+    tasks: [], runs: noWork ? [] : [{ status: Date.now() >= completesAt ? status : "running" }],
+    reply: Date.now() < completesAt ? "" : scenario.endsWith("choose-cli-context")
+      ? "```bash\npaperclipai context use acorn\npaperclipai context show --json\n```"
+      : '```bash\npaperclipai issue create --company-id <COMPANY_ID> --title "Website task" --project-id <PROJECT_ID> --assignee-agent-id <MORGAN_AGENT_ID>\n```',
+  }) as never);
+  vi.mocked(runOwnedCli).mockRejectedValue(new Error("Reached actual owned CLI boundary"));
+  const d = privilegedCliCases.find(row => row.scenarioId === scenario)!;
+  const act = () => Promise.resolve(d.act!(ctx, { project: { id: "launch" }, worker: { id: "morgan" } }));
+  return { ctx, act, completesAt: (value: number) => { completesAt = value; }, status: (value: string) => { status = value; }, noWork: () => { noWork = true; } };
+}
+for (const scenario of ["cli-operations.choose-cli-context", "cli-operations.create-from-cli"]) {
+  it(`${scenario}: reaches the genuine CLI boundary after160s only within its original clock`, async () => {
+    const f = fixture(scenario); const pending = f.act().then(() => null, error => error as Error);
+    await vi.advanceTimersByTimeAsync(160_000);
+    expect((await pending)?.message).toBe("Reached actual owned CLI boundary");
+    expect(runOwnedCli).toHaveBeenCalledOnce(); expect(f.ctx.observationDeadlineAt).toBe(start + 390_000);
+  });
+  it.each([undefined, NaN, Infinity, start, start - 1])(`${scenario}: rejects missing/invalid/expired deadline %s before observing or executing`, async deadline => {
+    const f = fixture(scenario); Object.assign(f.ctx, { observationDeadlineAt: deadline });
+    await expect(f.act()).rejects.toThrow(/Original privileged observation budget/);
+    expect(observeInternal).not.toHaveBeenCalled(); expect(runOwnedCli).not.toHaveBeenCalled();
+  });
+  it.each(["failed", "cancelled", "timed_out"])(`${scenario}: rejects stopped/failed native work %s`, async status => {
+    const f = fixture(scenario); f.completesAt(start); f.status(status);
+    await expect(f.act()).rejects.toThrow(/Canonical guidance run failed/);
+    expect(runOwnedCli).not.toHaveBeenCalled();
+  });
+  it(`${scenario}: a still-active or no-work turn cannot run CLI after its original deadline`, async () => {
+    for (const noWork of [false, true]) {
+      const f = fixture(scenario); Object.assign(f.ctx, { observationDeadlineAt: start + 1000 });
+      f.completesAt(start + 2000); if (noWork) { f.completesAt(start); f.noWork(); }
+      const pending = f.act().then(() => null, error => error as Error);
+      await vi.advanceTimersByTimeAsync(4000);
+      expect((await pending)?.message).toMatch(/Timed out waiting/); expect(runOwnedCli).not.toHaveBeenCalled();
+    }
+  });
+  it(`${scenario}: late observation cannot cross the CLI boundary`, async () => {
+    const f = fixture(scenario); Object.assign(f.ctx, { observationDeadlineAt: start + 1000 }); f.completesAt(start);
+    const original = vi.mocked(observeInternal).getMockImplementation()!;
+    vi.mocked(observeInternal).mockImplementation(async (...args) => { vi.setSystemTime(start + 1001); return original(...args); });
+    const pending = f.act().then(() => null, error => error as Error);
+    await vi.advanceTimersByTimeAsync(4000);
+    expect((await pending)?.message).toMatch(/Timed out waiting/); expect(runOwnedCli).not.toHaveBeenCalled();
+  });
+}
diff --git a/tests/runner-e2e/chat-catalog-domains/privileged-cli.test.ts b/tests/runner-e2e/chat-catalog-domains/privileged-cli.test.ts
index 9ef5dd5efed..8efc917bb89 100644
--- a/tests/runner-e2e/chat-catalog-domains/privileged-cli.test.ts
+++ b/tests/runner-e2e/chat-catalog-domains/privileged-cli.test.ts
@@ -1,7 +1,8 @@
-import { describe, expect, it } from "vitest";
+import { describe, expect, it, vi } from "vitest";
 import { websiteCreateArgv, validContextGuidance } from "./privileged-cli-support.js";
 import type { ChatCatalogContext } from "../chat-catalog-contract.js";
 import { privilegedCliCases, gradeChooseCliContext, gradeCreateFromCli } from "./privileged-cli.js";
+vi.mock("./internal-definition.js", () => ({ fixtureWorker: vi.fn() }));
 const target = { company: "owned-company", project: "launch", agent: "morgan", apiBase: "http://127.0.0.1:3100" };
 const command = (text: string) => `Use the explicit owned context.\n\`\`\`bash\n${text}\n\`\`\``;
 const valid = 'paperclipai issue create --company-id <COMPANY_ID> --title "Website task" --project-id <PROJECT_ID> --assignee-agent-id <MORGAN_AGENT_ID>';
diff --git a/tests/runner-e2e/chat-catalog-domains/privileged-cli.ts b/tests/runner-e2e/chat-catalog-domains/privileged-cli.ts
index 21bb87c00de..4d3ae80b555 100644
--- a/tests/runner-e2e/chat-catalog-domains/privileged-cli.ts
+++ b/tests/runner-e2e/chat-catalog-domains/privileged-cli.ts
@@ -5,7 +5,7 @@ import type { RuntimeAgent } from "./runtime-support.js";
 import type { ChatCatalogCase } from "../chat-catalog-contract.js";
 import { checks, project, entity, type Entity } from "./internal-support.js";
 import { fixtureWorker } from "./internal-definition.js";
-import { privilegedDefinition, privilegedObservation, settlePrivilegedChat } from "./privileged-support.js";
+import { privilegedDefinition, privilegedObservation, settlePrivilegedChat, remainingPrivilegedObservationBudget } from "./privileged-support.js";
 import { prepareOwnedCli, runOwnedCli, cleanupOwnedCli, websiteCreateArgv, validContextGuidance, contextGuidanceArgv } from "./privileged-cli-support.js";
 
 export function gradeCreateFromCli(value: unknown) {
@@ -38,7 +38,9 @@ const create = privilegedDefinition("cli-operations.create-from-cli", "privilege
     return { ...operator, project: launch, worker: paused, workerWasManuallyPaused: true };
   },
   async act(ctx, state) {
-    const reply = await settlePrivilegedChat(ctx);
+    remainingPrivilegedObservationBudget(ctx);
+    const reply = await settlePrivilegedChat(ctx, ctx.observationDeadlineAt);
+    remainingPrivilegedObservationBudget(ctx);
     state.tasksBeforeCli = reply.tasks.length;
     const fixture = { company: ctx.input.fixtures.company.id, project: entity(state, "project").id,
       agent: entity(state, "worker").id, apiBase: ctx.input.api.baseURL };
@@ -115,7 +117,9 @@ const context = privilegedDefinition("cli-operations.choose-cli-context", "privi
     return { ...operator, initialProfile: before.currentProfile, otherProfile: before.profiles.birch };
   },
   async act(ctx, state) {
-    const reply = await settlePrivilegedChat(ctx);
+    remainingPrivilegedObservationBudget(ctx);
+    const reply = await settlePrivilegedChat(ctx, ctx.observationDeadlineAt);
+    remainingPrivilegedObservationBudget(ctx);
     const returned = contextGuidanceArgv(reply.reply, { company: ctx.input.fixtures.company.id, apiBase: ctx.input.api.baseURL });
     if (!returned) throw new Error("Actual model context commands are unsupported or do not select and read back the intended profile");
     for (const argv of returned.commands) await runOwnedCli(ctx, argv);