diff --git a/CHANGELOG.md b/CHANGELOG.md
index df0399685e49..4549def773a6 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -17,6 +17,7 @@ Docs: https://docs.openclaw.ai
 - Plugins/Google: separate OAuth CSRF state from PKCE code verifier during Gemini browser sign-in so state validation and token exchange use independent values. (#59116) Thanks @eleqtrizit.
 - Exec/Windows: reject malformed drive-less rooted executable paths like `:\Users\...` so approval and allowlist candidate resolution no longer treat them as cwd-relative commands. (#58040) Thanks @SnowSky1.
 - Exec/preflight: fail closed on complex interpreter invocations that would otherwise skip script-content validation, and correctly inspect quoted script paths before host execution. Thanks @pgondhi987.
+- Exec/Windows: include Windows-compatible env override keys like `ProgramFiles(x86)` in system-run approval binding so changed approved values are rejected instead of silently passing unbound. (#59182) Thanks @pgondhi987.
 
 ## 2026.4.2-beta.1
 
diff --git a/extensions/discord/src/monitor/agent-components.wildcard.test.ts b/extensions/discord/src/monitor/agent-components.wildcard.test.ts
index 575389241b65..04d484cc022a 100644
--- a/extensions/discord/src/monitor/agent-components.wildcard.test.ts
+++ b/extensions/discord/src/monitor/agent-components.wildcard.test.ts
@@ -1,7 +1,7 @@
-import { beforeAll, describe, expect, it } from "vitest";
+import { beforeAll, describe, expect, it, vi } from "vitest";
 
-let buildDiscordComponentCustomId: typeof import("../component-custom-id.js").buildDiscordComponentCustomId;
-let buildDiscordModalCustomId: typeof import("../component-custom-id.js").buildDiscordModalCustomId;
+let buildDiscordComponentCustomId: typeof import("../components.js").buildDiscordComponentCustomId;
+let buildDiscordModalCustomId: typeof import("../components.js").buildDiscordModalCustomId;
 let createDiscordComponentButton: typeof import("./agent-components.js").createDiscordComponentButton;
 let createDiscordComponentChannelSelect: typeof import("./agent-components.js").createDiscordComponentChannelSelect;
 let createDiscordComponentMentionableSelect: typeof import("./agent-components.js").createDiscordComponentMentionableSelect;
@@ -11,8 +11,7 @@ let createDiscordComponentStringSelect: typeof import("./agent-components.js").c
 let createDiscordComponentUserSelect: typeof import("./agent-components.js").createDiscordComponentUserSelect;
 
 beforeAll(async () => {
-  ({ buildDiscordComponentCustomId, buildDiscordModalCustomId } =
-    await import("../component-custom-id.js"));
+  ({ buildDiscordComponentCustomId, buildDiscordModalCustomId } = await import("../components.js"));
   ({
     createDiscordComponentButton,
     createDiscordComponentChannelSelect,
diff --git a/src/gateway/node-invoke-system-run-approval-match.test.ts b/src/gateway/node-invoke-system-run-approval-match.test.ts
index a3713b970ab4..8f35e3c1068b 100644
--- a/src/gateway/node-invoke-system-run-approval-match.test.ts
+++ b/src/gateway/node-invoke-system-run-approval-match.test.ts
@@ -123,6 +123,32 @@ describe("evaluateSystemRunApprovalMatch", () => {
     expect(result).toEqual({ ok: true });
   });
 
+  test("rejects mismatched Windows-compatible env override values", () => {
+    const result = evaluateSystemRunApprovalMatch({
+      argv: ["cmd.exe", "/c", "echo ok"],
+      request: {
+        host: "node",
+        command: "cmd.exe /c echo ok",
+        systemRunBinding: buildSystemRunApprovalBinding({
+          argv: ["cmd.exe", "/c", "echo ok"],
+          cwd: null,
+          agentId: null,
+          sessionKey: null,
+          env: { "ProgramFiles(x86)": "C:\\Program Files (x86)" },
+        }).binding,
+      },
+      binding: {
+        ...defaultBinding,
+        env: { "ProgramFiles(x86)": "D:\\malicious" },
+      },
+    });
+    expect(result.ok).toBe(false);
+    if (result.ok) {
+      throw new Error("unreachable");
+    }
+    expect(result.code).toBe("APPROVAL_ENV_MISMATCH");
+  });
+
   test("rejects non-node host requests", () => {
     const result = evaluateSystemRunApprovalMatch({
       argv: ["echo", "SAFE"],
diff --git a/src/gateway/server-methods/server-methods.test.ts b/src/gateway/server-methods/server-methods.test.ts
index 540f04c880bd..2c3f7697ed84 100644
--- a/src/gateway/server-methods/server-methods.test.ts
+++ b/src/gateway/server-methods/server-methods.test.ts
@@ -656,6 +656,37 @@ describe("exec approval handlers", () => {
     );
   });
 
+  it("includes Windows-compatible env keys in approval env bindings", async () => {
+    const { handlers, broadcasts, respond, context } = createExecApprovalFixture();
+    await requestExecApproval({
+      handlers,
+      respond,
+      context,
+      params: {
+        timeoutMs: 10,
+        commandArgv: ["cmd.exe", "/c", "echo", "ok"],
+        command: "cmd.exe /c echo ok",
+        env: {
+          "ProgramFiles(x86)": "C:\\Program Files (x86)",
+        },
+      },
+    });
+    const requested = broadcasts.find((entry) => entry.event === "exec.approval.requested");
+    expect(requested).toBeTruthy();
+    const request = (requested?.payload as { request?: Record<string, unknown> })?.request ?? {};
+    const envBinding = buildSystemRunApprovalEnvBinding({
+      "ProgramFiles(x86)": "C:\\Program Files (x86)",
+    });
+    expect(request["envKeys"]).toEqual(envBinding.envKeys);
+    expect(request["systemRunBinding"]).toEqual(
+      buildSystemRunApprovalBinding({
+        argv: ["cmd.exe", "/c", "echo", "ok"],
+        cwd: "/tmp",
+        env: { "ProgramFiles(x86)": "C:\\Program Files (x86)" },
+      }).binding,
+    );
+  });
+
   it("stores sorted env keys for gateway approvals without node-only binding", async () => {
     const { handlers, broadcasts, respond, context } = createExecApprovalFixture();
     await requestExecApproval({
diff --git a/src/infra/host-env-security.ts b/src/infra/host-env-security.ts
index c6ac3dded611..83ed5f437904 100644
--- a/src/infra/host-env-security.ts
+++ b/src/infra/host-env-security.ts
@@ -68,7 +68,7 @@ export function normalizeEnvVarKey(
   return key;
 }
 
-function normalizeHostOverrideEnvVarKey(rawKey: string): string | null {
+export function normalizeHostOverrideEnvVarKey(rawKey: string): string | null {
   const key = normalizeEnvVarKey(rawKey);
   if (!key) {
     return null;
diff --git a/src/infra/system-run-approval-binding.test.ts b/src/infra/system-run-approval-binding.test.ts
index 6963f482423c..fe1eee52ce1a 100644
--- a/src/infra/system-run-approval-binding.test.ts
+++ b/src/infra/system-run-approval-binding.test.ts
@@ -117,6 +117,19 @@ describe("buildSystemRunApprovalEnvBinding", () => {
       envKeys: [],
     });
   });
+
+  it("includes Windows-compatible override keys in env binding", () => {
+    const base = buildSystemRunApprovalEnvBinding({
+      "ProgramFiles(x86)": "C:\\Program Files (x86)",
+    });
+    const changed = buildSystemRunApprovalEnvBinding({
+      "ProgramFiles(x86)": "D:\\SDKs",
+    });
+
+    expect(base.envKeys).toEqual(["ProgramFiles(x86)"]);
+    expect(base.envHash).toBeTypeOf("string");
+    expect(base.envHash).not.toEqual(changed.envHash);
+  });
 });
 
 describe("buildSystemRunApprovalBinding", () => {
@@ -175,6 +188,20 @@ describe("matchSystemRunApprovalEnvHash", () => {
         details: { envKeys: ["ALPHA"] },
       },
     },
+    {
+      name: "reports missing approval env binding when actual env keys are present without hashes",
+      params: {
+        expectedEnvHash: null,
+        actualEnvHash: null,
+        actualEnvKeys: ["ProgramFiles(x86)"],
+      },
+      expected: {
+        ok: false,
+        code: "APPROVAL_ENV_BINDING_MISSING",
+        message: "approval id missing env binding for requested env overrides",
+        details: { envKeys: ["ProgramFiles(x86)"] },
+      },
+    },
     {
       name: "reports env hash mismatches",
       params: {
diff --git a/src/infra/system-run-approval-binding.ts b/src/infra/system-run-approval-binding.ts
index 87a137014f10..87f91cc884be 100644
--- a/src/infra/system-run-approval-binding.ts
+++ b/src/infra/system-run-approval-binding.ts
@@ -4,7 +4,7 @@ import type {
   SystemRunApprovalFileOperand,
   SystemRunApprovalPlan,
 } from "./exec-approvals.js";
-import { normalizeEnvVarKey } from "./host-env-security.js";
+import { normalizeHostOverrideEnvVarKey } from "./host-env-security.js";
 import { normalizeNonEmptyString, normalizeStringArray } from "./system-run-normalize.js";
 
 type NormalizedSystemRunEnvEntry = [key: string, value: string];
@@ -75,7 +75,7 @@ function normalizeSystemRunEnvEntries(env: unknown): NormalizedSystemRunEnvEntry
     if (typeof rawValue !== "string") {
       continue;
     }
-    const key = normalizeEnvVarKey(rawKey, { portable: true });
+    const key = normalizeHostOverrideEnvVarKey(rawKey);
     if (!key) {
       continue;
     }
@@ -162,6 +162,16 @@ export function matchSystemRunApprovalEnvHash(params: {
   actualEnvHash: string | null;
   actualEnvKeys: string[];
 }): SystemRunApprovalMatchResult {
+  // Fail closed if callers provide inconsistent hash/key state. This guards against
+  // normalization drift between approval and execution paths.
+  if (!params.expectedEnvHash && !params.actualEnvHash && params.actualEnvKeys.length > 0) {
+    return {
+      ok: false,
+      code: "APPROVAL_ENV_BINDING_MISSING",
+      message: "approval id missing env binding for requested env overrides",
+      details: { envKeys: params.actualEnvKeys },
+    };
+  }
   if (!params.expectedEnvHash && !params.actualEnvHash) {
     return { ok: true };
   }
diff --git a/test/fixtures/system-run-approval-binding-contract.json b/test/fixtures/system-run-approval-binding-contract.json
index 6d96c388e66d..10b3008c39d5 100644
--- a/test/fixtures/system-run-approval-binding-contract.json
+++ b/test/fixtures/system-run-approval-binding-contract.json
@@ -48,6 +48,30 @@
       },
       "expected": { "ok": false, "code": "APPROVAL_ENV_MISMATCH" }
     },
+    {
+      "name": "binding rejects mismatched Windows-compatible env values",
+      "request": {
+        "host": "node",
+        "command": "cmd.exe /c echo ok",
+        "binding": {
+          "argv": ["cmd.exe", "/c", "echo", "ok"],
+          "cwd": null,
+          "agentId": null,
+          "sessionKey": null,
+          "env": { "ProgramFiles(x86)": "C:\\Program Files (x86)" }
+        }
+      },
+      "invoke": {
+        "argv": ["cmd.exe", "/c", "echo", "ok"],
+        "binding": {
+          "cwd": null,
+          "agentId": null,
+          "sessionKey": null,
+          "env": { "ProgramFiles(x86)": "D:\\malicious" }
+        }
+      },
+      "expected": { "ok": false, "code": "APPROVAL_ENV_MISMATCH" }
+    },
     {
       "name": "binding rejects unbound env overrides",
       "request": {