diff --git a/CHANGELOG.md b/CHANGELOG.md
index 36e320e62c8..5b4a1dbba7d 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -102,6 +102,7 @@ Docs: https://docs.openclaw.ai
 - Matrix/media: surface a dedicated `[matrix <kind> attachment too large]` marker for oversized inbound media instead of the generic unavailable marker, and classify size-limit failures with a typed Matrix error. (#60289) Thanks @efe-arv.
 - WhatsApp/watchdog: reset watchdog timeout after reconnect so quiet channels no longer enter a tight reconnect loop from stale message timestamps carried across connection runs. (#60007) Thanks @MonkeyLeeT.
 - Agents/fallback: persist selected fallback overrides before retry attempts start, prefer persisted overrides during live-session reconciliation, and keep provider-scoped auth-profile failover from snapping retries back to stale primary selections.
+- Agents/MCP: sort MCP tools deterministically by name so the tools block in API requests is stable across turns, preventing unnecessary prompt-cache busting from non-deterministic `listTools()` order. (#58037) Thanks @bcherny.
 
 ## 2026.4.2
 
diff --git a/src/agents/pi-bundle-mcp-materialize.ts b/src/agents/pi-bundle-mcp-materialize.ts
index 65c335c5ef9..7a1b95a38e9 100644
--- a/src/agents/pi-bundle-mcp-materialize.ts
+++ b/src/agents/pi-bundle-mcp-materialize.ts
@@ -101,6 +101,11 @@ export async function materializeBundleMcpToolsForRun(params: {
     });
   }
 
+  // Sort tools deterministically by name so the tools block in API requests is
+  // stable across turns. MCP's listTools() does not guarantee order, and any
+  // change in the tools array busts the prompt cache at the tools block.
+  tools.sort((a, b) => a.name.localeCompare(b.name));
+
   return {
     tools,
     dispose: async () => {
diff --git a/src/agents/pi-bundle-mcp-test-harness.ts b/src/agents/pi-bundle-mcp-test-harness.ts
index ffb7a2a310a..a5b5de9274b 100644
--- a/src/agents/pi-bundle-mcp-test-harness.ts
+++ b/src/agents/pi-bundle-mcp-test-harness.ts
@@ -25,7 +25,7 @@ export async function makeTempDir(prefix: string): Promise<string> {
   return dir;
 }
 
-async function writeExecutable(filePath: string, content: string): Promise<void> {
+export async function writeExecutable(filePath: string, content: string): Promise<void> {
   await fs.mkdir(path.dirname(filePath), { recursive: true });
   await fs.writeFile(filePath, content, { encoding: "utf-8", mode: 0o755 });
 }
diff --git a/src/agents/pi-bundle-mcp-tools.materialize.test.ts b/src/agents/pi-bundle-mcp-tools.materialize.test.ts
index 45f5db4f170..00e4ae77f77 100644
--- a/src/agents/pi-bundle-mcp-tools.materialize.test.ts
+++ b/src/agents/pi-bundle-mcp-tools.materialize.test.ts
@@ -1,3 +1,4 @@
+import { createRequire } from "node:module";
 import path from "node:path";
 import { afterEach, describe, expect, it } from "vitest";
 import {
@@ -6,9 +7,14 @@ import {
   startSseProbeServer,
   writeBundleProbeMcpServer,
   writeClaudeBundle,
+  writeExecutable,
 } from "./pi-bundle-mcp-test-harness.js";
 import { createBundleMcpToolRuntime } from "./pi-bundle-mcp-tools.js";
 
+const require = createRequire(import.meta.url);
+const SDK_SERVER_MCP_PATH = require.resolve("@modelcontextprotocol/sdk/server/mcp.js");
+const SDK_SERVER_STDIO_PATH = require.resolve("@modelcontextprotocol/sdk/server/stdio.js");
+
 afterEach(async () => {
   await cleanupBundleMcpHarness();
 });
@@ -154,4 +160,43 @@ describe("createBundleMcpToolRuntime", () => {
       await sseServer.close();
     }
   });
+
+  it("returns tools sorted alphabetically for stable prompt-cache keys", async () => {
+    const workspaceDir = await makeTempDir("openclaw-bundle-mcp-tools-");
+    const serverScriptPath = path.join(workspaceDir, "servers", "multi-tool.mjs");
+    // Register tools in non-alphabetical order; runtime must sort them.
+    await writeExecutable(
+      serverScriptPath,
+      `#!/usr/bin/env node
+import { McpServer } from ${JSON.stringify(SDK_SERVER_MCP_PATH)};
+import { StdioServerTransport } from ${JSON.stringify(SDK_SERVER_STDIO_PATH)};
+const server = new McpServer({ name: "multi", version: "1.0.0" });
+server.tool("zeta", "z", async () => ({ content: [{ type: "text", text: "z" }] }));
+server.tool("alpha", "a", async () => ({ content: [{ type: "text", text: "a" }] }));
+server.tool("mu", "m", async () => ({ content: [{ type: "text", text: "m" }] }));
+await server.connect(new StdioServerTransport());
+`,
+    );
+
+    const runtime = await createBundleMcpToolRuntime({
+      workspaceDir,
+      cfg: {
+        mcp: {
+          servers: {
+            multi: { command: "node", args: [serverScriptPath] },
+          },
+        },
+      },
+    });
+
+    try {
+      expect(runtime.tools.map((tool) => tool.name)).toEqual([
+        "multi__alpha",
+        "multi__mu",
+        "multi__zeta",
+      ]);
+    } finally {
+      await runtime.dispose();
+    }
+  });
 });