diff --git a/apps/cloud/src/mcp/session-build-semaphore.test.ts b/apps/cloud/src/mcp/session-build-semaphore.test.ts
index 3d4ad7634..584b65ee0 100644
--- a/apps/cloud/src/mcp/session-build-semaphore.test.ts
+++ b/apps/cloud/src/mcp/session-build-semaphore.test.ts
@@ -1,4 +1,4 @@
-import { describe, expect, it, beforeEach } from "@effect/vitest";
+import { describe, expect, it, beforeEach, afterEach, vi } from "@effect/vitest";
 
 import {
   acquireBuildSlot,
@@ -13,6 +13,10 @@ describe("session-build-semaphore", () => {
     resetBuildSlotsForTest();
   });
 
+  afterEach(() => {
+    vi.useRealTimers();
+  });
+
   it("grants up to the cap immediately, with no wait", async () => {
     const results = await Promise.all([
       acquireBuildSlot().promise,
@@ -214,6 +218,7 @@ describe("session-build-semaphore", () => {
   });
 
   it("proceeds without a slot when the queue wait exceeds the timeout, and does not count it as active", async () => {
+    vi.useFakeTimers();
     await Promise.all([
       acquireBuildSlot().promise,
       acquireBuildSlot().promise,
@@ -223,6 +228,10 @@ describe("session-build-semaphore", () => {
     expect(currentActiveBuildsForTest()).toBe(4);
 
     const timedOutHandle = acquireBuildSlot(10);
+    await vi.advanceTimersByTimeAsync(9);
+    expect(currentQueueLengthForTest()).toBe(1);
+    expect(currentActiveBuildsForTest()).toBe(4);
+    await vi.advanceTimersByTimeAsync(1);
     const result = await timedOutHandle.promise;
 
     expect(result).toEqual({ acquired: false, waitMs: expect.any(Number), timedOut: true });
diff --git a/e2e/cloud/mcp-session-cap-eviction.test.ts b/e2e/cloud/mcp-session-cap-eviction.test.ts
index 8724edd5a..8103eef5c 100644
--- a/e2e/cloud/mcp-session-cap-eviction.test.ts
+++ b/e2e/cloud/mcp-session-cap-eviction.test.ts
@@ -19,8 +19,8 @@
 // the whole boot (see that file for the value and its headroom story), so
 // this test can cross it with a bounded number of real sessions instead of
 // registering the production default of 32.
-import { expect } from "@effect/vitest";
-import { Effect, Schedule } from "effect";
+import { expect, it } from "@effect/vitest";
+import { Effect, Option, Schedule, Schema } from "effect";
 
 import { scenario } from "../src/scenario";
 import { Mcp, Target, Telemetry } from "../src/services";
@@ -52,6 +52,68 @@ const postJson = (mcpUrl: string, bearer: string, body: unknown, sessionId?: str
     body: JSON.stringify(body),
   });
 
+const decodeRestartEnvelope = Schema.decodeUnknownOption(
+  Schema.fromJsonString(
+    Schema.Struct({
+      jsonrpc: Schema.Literal("2.0"),
+      id: Schema.Null,
+      error: Schema.Struct({
+        code: Schema.Literal(-32001),
+        message: Schema.Literal("MCP session is restarting, please retry"),
+      }),
+    }),
+  ),
+);
+
+const isRestartResponse = (status: number, body: string): boolean =>
+  status === 503 && Option.isSome(decodeRestartEnvelope(body));
+
+it.each([
+  [
+    503,
+    {
+      jsonrpc: "2.0",
+      id: null,
+      error: { code: -32001, message: "MCP session is restarting, please retry" },
+    },
+    true,
+  ],
+  [
+    404,
+    {
+      jsonrpc: "2.0",
+      id: null,
+      error: { code: -32001, message: "MCP session is restarting, please retry" },
+    },
+    false,
+  ],
+  [
+    503,
+    {
+      jsonrpc: "2.0",
+      id: null,
+      error: { code: -32603, message: "MCP session is restarting, please retry" },
+    },
+    false,
+  ],
+  [
+    503,
+    {
+      jsonrpc: "2.0",
+      id: null,
+      error: { code: -32001, message: "MCP session is restarting unexpectedly" },
+    },
+    false,
+  ],
+  [503, { error: "MCP session is restarting, please retry" }, false],
+] as const)("only retries the documented restart envelope (%s, %j)", (status, body, retry) => {
+  expect(isRestartResponse(status, JSON.stringify(body))).toBe(retry);
+});
+
+it("does not retry malformed restart responses", () => {
+  expect(isRestartResponse(503, "MCP session is restarting, please retry")).toBe(false);
+});
+
 /**
  * Opens one fresh MCP session under an already-minted bearer. `initialize`
  * without an existing `mcp-session-id` always mints a new session, the same
@@ -73,21 +135,42 @@ const openSession = async (
   label: string,
   recordSession: (sessionId: string) => void,
 ): Promise<string> => {
-  const initialized = await postJson(mcpUrl, bearer, {
-    jsonrpc: "2.0" as const,
-    id: "initialize",
-    method: "initialize",
-    params: {
-      protocolVersion: PROTOCOL_VERSION,
-      capabilities: {},
-      clientInfo: { name: `executor-e2e-cap-eviction-${label}`, version: "0.0.1" },
-    },
-  });
-  const sessionId = initialized.headers.get("mcp-session-id");
-  if (!sessionId) {
+  // The platform can reset a session Durable Object while its initialize
+  // is in flight, and the server answers that with the documented restart
+  // envelope (503, -32001, "MCP session is restarting, please retry") — the
+  // same contract a streamable-http client follows: same request, after the
+  // advertised delay. Treat it as transient here instead of failing the
+  // scenario on a retryable platform blip.
+  const RESTART_ATTEMPTS = 8;
+  const RESTART_DELAY_MS = 2_000; // The host advertises Retry-After: 2.
+  let minted: { readonly response: Response; readonly sessionId: string } | undefined;
+  for (let attempt = 0; attempt < RESTART_ATTEMPTS; attempt += 1) {
+    const response = await postJson(mcpUrl, bearer, {
+      jsonrpc: "2.0" as const,
+      id: "initialize",
+      method: "initialize",
+      params: {
+        protocolVersion: PROTOCOL_VERSION,
+        capabilities: {},
+        clientInfo: { name: `executor-e2e-cap-eviction-${label}`, version: "0.0.1" },
+      },
+    });
+    const candidate = response.headers.get("mcp-session-id");
+    if (candidate !== null && candidate.length > 0) {
+      minted = { response, sessionId: candidate };
+      break;
+    }
+    const body = await response.text();
+    const isRestart = isRestartResponse(response.status, body);
+    if (!isRestart) break;
+    if (attempt === RESTART_ATTEMPTS - 1) break;
+    await new Promise((resolve) => setTimeout(resolve, RESTART_DELAY_MS));
+  }
+  if (!minted) {
     // oxlint-disable-next-line executor/no-error-constructor -- boundary: e2e setup precondition.
     throw new Error(`openSession (${label}): no mcp-session-id header`);
   }
+  const { response: initialized, sessionId } = minted;
   // Recorded the moment the id exists — BEFORE the body read and status
   // assertion below, either of which can throw with the session already live
   // on the server. The cleanup finalizer needs the id on every one of those