@@ -0,0 +1,76 @@
+#!/usr/bin/env node
+
+/**
+ * tools/list ordering negative test server.
+ *
+ * Speaks the sessionless 2026-07-28 wire (SEP-2575) and advertises the same
+ * four tools on every tools/list request, but rotates the list by one
+ * position each time (it keeps a call counter for that, nothing else). The set never changes, only the order, which violates the
+ * 2026-07-28 SHOULD "Servers SHOULD return tools in a deterministic order".
+ * The tools-list scenario should emit WARNING for
+ * tools-list-deterministic-order against this server while tools-list itself
+ * still passes, since every response is structurally valid.
+ */
+
+import express from 'express';
+
+const app = express();
+app.use(express.json());
+
+const TOOLS = ['alpha', 'bravo', 'charlie', 'delta'].map((name) => ({
+  name,
+  description: `Fixture tool ${name}`,
+  inputSchema: { type: 'object', properties: {} }
+}));
+
+let listCalls = 0;
+
+app.post('/mcp', (req, res) => {
+  const body = req.body || {};
+  const id = body.id ?? null;
+  const method = body.method;
+
+  switch (method) {
+    case 'server/discover':
+      return res.json({
+        jsonrpc: '2.0',
+        id,
+        result: {
+          resultType: 'complete',
+          ttlMs: 0,
+          cacheScope: 'private',
+          supportedVersions: ['2026-07-28'],
+          capabilities: { tools: {} },
+          serverInfo: { name: 'tools-list-rotated-order', version: '1.0.0' }
+        }
+      });
+    case 'tools/list': {
+      // Rotate by one position per call: the same set, never the same order.
+      const offset = listCalls++ % TOOLS.length;
+      const tools = [...TOOLS.slice(offset), ...TOOLS.slice(0, offset)];
+      return res.json({
+        jsonrpc: '2.0',
+        id,
+        result: {
+          resultType: 'complete',
+          ttlMs: 0,
+          cacheScope: 'private',
+          tools
+        }
+      });
+    }
+    default:
+      return res.status(404).json({
+        jsonrpc: '2.0',
+        id,
+        error: { code: -32601, message: 'Method not found' }
+      });
+  }
+});
+
+const PORT = parseInt(process.env.PORT || '3008', 10);
+app.listen(PORT, '127.0.0.1', () => {
+  console.log(
+    `tools/list rotated-order negative test server running on http://localhost:${PORT}/mcp`
+  );
+});
@@ -4,11 +4,11 @@ import path from 'path';
 import { DNSRebindingProtectionScenario } from './dns-rebinding';
 import { ResourcesNotFoundErrorScenario } from './resources';
 import { CachingScenario } from './caching';
+import { ToolsListScenario } from './tools';
 import {
   JsonSchema2020_12Scenario,
   sep2106KeywordCheckStatus
 } from './json-schema-2020-12';
-import { ToolsListScenario } from './tools';
 import { DRAFT_PROTOCOL_VERSION, LATEST_SPEC_VERSION } from '../../types';
 import { takeWireViolations } from '../../validation/wire-schema';
 
@@ -217,6 +217,43 @@ describe('Server scenario negative tests', () => {
     }, 10000);
   });
 
+  describe('tools-list-deterministic-order', () => {
+    let serverProcess: ChildProcess | null = null;
+    const PORT = 3008;
+
+    beforeAll(async () => {
+      serverProcess = await startServer(
+        path.join(
+          process.cwd(),
+          'examples/servers/typescript/tools-list-rotated-order.ts'
+        ),
+        PORT
+      );
+    }, 35000);
+
+    afterAll(async () => {
+      await stopServer(serverProcess);
+    });
+
+    it('emits WARNING for deterministic-order while tools-list still passes against a server that rotates its tool list', async () => {
+      const scenario = new ToolsListScenario();
+      const checks = await scenario.run(
+        testContext(`http://localhost:${PORT}/mcp`, DRAFT_PROTOCOL_VERSION)
+      );
+
+      const list = checks.find((c) => c.id === 'tools-list');
+      expect(list?.status).toBe('SUCCESS');
+
+      const order = checks.find(
+        (c) => c.id === 'tools-list-deterministic-order'
+      );
+      expect(order?.status).toBe('WARNING');
+      expect(order?.errorMessage).toMatch(/different order/);
+      expect(order?.details).toMatchObject({ toolCount: 4, probes: 3 });
+      expect(order?.details?.untestable).toBeUndefined();
+    }, 10000);
+  });
+
   describe('tools-name-format', () => {
     let serverProcess: ChildProcess | null = null;
     const PORT = 3009;
 
@@ -1,5 +1,6 @@
 import { describe, it, expect } from 'vitest';
 import {
+  buildToolsListDeterministicOrderCheck,
   buildToolsNameFormatCheck,
   toolNameFormatCheckApplies,
   ToolsListScenario,
@@ -193,3 +194,143 @@ describe('ToolsListScenario version gate', () => {
     );
   });
 });
+
+describe('buildToolsListDeterministicOrderCheck', () => {
+  const names = (...ns: string[]) => ns.map((name) => ({ name }));
+
+  it('returns SUCCESS when every probe lists the same tools in the same order', () => {
+    const check = buildToolsListDeterministicOrderCheck([
+      names('a', 'b', 'c'),
+      names('a', 'b', 'c'),
+      names('a', 'b', 'c')
+    ]);
+    expect(check.id).toBe('tools-list-deterministic-order');
+    expect(check.status).toBe('SUCCESS');
+    expect(check.errorMessage).toBeUndefined();
+    expect(check.details).toEqual({
+      toolCount: 3,
+      probes: 3,
+      orders: [
+        ['a', 'b', 'c'],
+        ['a', 'b', 'c'],
+        ['a', 'b', 'c']
+      ]
+    });
+    expect(check.specReferences?.[0]?.url).toContain('2026-07-28/server/tools');
+  });
+
+  it('returns WARNING when the same tools come back in a different order', () => {
+    const check = buildToolsListDeterministicOrderCheck([
+      names('a', 'b', 'c'),
+      names('b', 'c', 'a'),
+      names('c', 'a', 'b')
+    ]);
+    expect(check.status).toBe('WARNING');
+    expect(check.errorMessage).toMatch(/different order/);
+    expect(check.errorMessage).toMatch(/index 0/);
+    expect(check.details).toMatchObject({ toolCount: 3, probes: 3 });
+    expect(check.details?.untestable).toBeUndefined();
+    expect(check.details?.orders).toEqual([
+      ['a', 'b', 'c'],
+      ['b', 'c', 'a'],
+      ['c', 'a', 'b']
+    ]);
+  });
+
+  it('flags a divergence that only appears on the last probe', () => {
+    const check = buildToolsListDeterministicOrderCheck([
+      names('a', 'b', 'c'),
+      names('a', 'b', 'c'),
+      names('a', 'c', 'b')
+    ]);
+    expect(check.status).toBe('WARNING');
+    expect(check.errorMessage).toMatch(/probe 3/);
+    expect(check.errorMessage).toMatch(/index 1/);
+  });
+
+  it('reports untestable (WARNING) when the set of tools changed between probes', () => {
+    const check = buildToolsListDeterministicOrderCheck([
+      names('a', 'b', 'c'),
+      names('a', 'b', 'd')
+    ]);
+    expect(check.status).toBe('WARNING');
+    expect(check.errorMessage).toMatch(/^Not testable: /);
+    expect(check.errorMessage).toMatch(/added: d/);
+    expect(check.errorMessage).toMatch(/removed: c/);
+    expect(check.details).toMatchObject({ untestable: true });
+  });
+
+  it('reports untestable (WARNING) when a probe returned no tools array', () => {
+    const check = buildToolsListDeterministicOrderCheck([
+      names('a', 'b'),
+      undefined
+    ]);
+    expect(check.status).toBe('WARNING');
+    expect(check.errorMessage).toMatch(/^Not testable: /);
+    expect(check.details).toMatchObject({ untestable: true });
+  });
+
+  it('reports untestable (WARNING) with fewer than two probes', () => {
+    const check = buildToolsListDeterministicOrderCheck([names('a', 'b')]);
+    expect(check.status).toBe('WARNING');
+    expect(check.errorMessage).toMatch(/^Not testable: /);
+  });
+
+  it('returns INFO when no probe saw two tools to order', () => {
+    const one = buildToolsListDeterministicOrderCheck([names('a'), names('a')]);
+    expect(one.status).toBe('INFO');
+    expect(one.errorMessage).toMatch(/nothing to compare/);
+    expect(one.details).toEqual({
+      toolCount: 1,
+      probes: 2,
+      orders: [['a'], ['a']]
+    });
+    const none = buildToolsListDeterministicOrderCheck([[], []]);
+    expect(none.status).toBe('INFO');
+  });
+
+  it('reports untestable when a probe grows from one tool to two', () => {
+    const check = buildToolsListDeterministicOrderCheck([
+      names('a'),
+      names('a', 'b')
+    ]);
+    expect(check.status).toBe('WARNING');
+    expect(check.errorMessage).toMatch(/^Not testable: /);
+    expect(check.errorMessage).toMatch(/added: b/);
+  });
+
+  it('treats a tool without a string name as one placeholder entry', () => {
+    const check = buildToolsListDeterministicOrderCheck([
+      [{ name: 'a' }, { name: 42 }],
+      [{ name: 42 }, { name: 'a' }]
+    ]);
+    expect(check.status).toBe('WARNING');
+    expect(check.errorMessage).toMatch(/different order/);
+    expect(check.details?.orders).toEqual([
+      ['a', '<tool missing name>'],
+      ['<tool missing name>', 'a']
+    ]);
+  });
+
+  it('treats duplicate names as a set change only when their multiplicity changes', () => {
+    const stable = buildToolsListDeterministicOrderCheck([
+      names('a', 'a', 'b'),
+      names('a', 'a', 'b')
+    ]);
+    expect(stable.status).toBe('SUCCESS');
+    const changed = buildToolsListDeterministicOrderCheck([
+      names('a', 'a', 'b'),
+      names('a', 'b', 'b')
+    ]);
+    expect(changed.status).toBe('WARNING');
+    expect(changed.errorMessage).toMatch(/^Not testable: /);
+  });
+
+  it('gates itself to the 2026-07-28 wire', () => {
+    const check = buildToolsListDeterministicOrderCheck([
+      names('a', 'b'),
+      names('a', 'b')
+    ]);
+    expect(check.source).toEqual({ introducedIn: '2026-07-28' });
+  });
+});