diff --git a/CHANGELOG.md b/CHANGELOG.md
index 60a4a8748..d6eb2d81b 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -305,6 +305,7 @@ Docs: https://docs.openclaw.ai
 - Media/mime unknown-kind handling: return `undefined` (not `"unknown"`) for missing/unrecognized MIME kinds and use document-size fallback caps for unknown remote media, preventing phantom `<media:unknown>` Signal events from being treated as real messages. (#39199) Thanks @nicolasgrasset.
 - Nodes/system.run allow-always persistence: honor shell comment semantics during allowlist analysis so `#`-tailed payloads that never execute are not persisted as trusted follow-up commands. Thanks @tdjackey for reporting.
 - Signal/inbound attachment fan-in: forward all successfully fetched inbound attachments through `MediaPaths`/`MediaUrls`/`MediaTypes` (instead of only the first), and improve multi-attachment placeholder summaries in mention-gated pending history. (#39212) Thanks @joeykrug.
+- Nodes/system.run dispatch-wrapper boundary: keep shell-wrapper approval classification active at the depth boundary so `env` wrapper stacks cannot reach `/bin/sh -c` execution without the expected approval gate. Thanks @tdjackey for reporting.
 
 ## 2026.3.2
 
diff --git a/src/infra/exec-wrapper-resolution.ts b/src/infra/exec-wrapper-resolution.ts
index 95489abe8..aaa56c221 100644
--- a/src/infra/exec-wrapper-resolution.ts
+++ b/src/infra/exec-wrapper-resolution.ts
@@ -509,7 +509,9 @@ function hasEnvManipulationBeforeShellWrapperInternal(
   depth: number,
   envManipulationSeen: boolean,
 ): boolean {
-  if (depth >= MAX_DISPATCH_WRAPPER_DEPTH) {
+  // The wrapper found exactly at the configured dispatch depth boundary still needs
+  // to participate in approval classification; only paths beyond that boundary fail closed.
+  if (depth > MAX_DISPATCH_WRAPPER_DEPTH) {
     return false;
   }
 
@@ -607,7 +609,9 @@ function extractShellWrapperCommandInternal(
   rawCommand: string | null,
   depth: number,
 ): ShellWrapperCommand {
-  if (depth >= MAX_DISPATCH_WRAPPER_DEPTH) {
+  // The shell wrapper reached at the boundary depth is still semantically relevant.
+  // Only deeper wrapper stacks should be dropped as overflow.
+  if (depth > MAX_DISPATCH_WRAPPER_DEPTH) {
     return { isWrapper: false, command: null };
   }
 
diff --git a/src/infra/system-run-command.test.ts b/src/infra/system-run-command.test.ts
index 83d64533b..421f3522a 100644
--- a/src/infra/system-run-command.test.ts
+++ b/src/infra/system-run-command.test.ts
@@ -54,6 +54,17 @@ describe("system run command helpers", () => {
         "echo hi",
       ]),
     ).toBe("echo hi");
+    expect(
+      extractShellCommandFromArgv([
+        "/usr/bin/env",
+        "/usr/bin/env",
+        "/usr/bin/env",
+        "/usr/bin/env",
+        "/bin/sh",
+        "-c",
+        "echo hi",
+      ]),
+    ).toBe("echo hi");
   });
 
   test("extractShellCommandFromArgv supports fish and pwsh wrappers", () => {
diff --git a/src/node-host/invoke-system-run.test.ts b/src/node-host/invoke-system-run.test.ts
index 3134629af..9b1fbecd8 100644
--- a/src/node-host/invoke-system-run.test.ts
+++ b/src/node-host/invoke-system-run.test.ts
@@ -858,6 +858,46 @@ describe("handleSystemRunInvoke mac app exec host routing", () => {
     expectApprovalRequiredDenied({ sendNodeEvent, sendInvokeResult });
   });
 
+  it("denies env-wrapped shell payloads at the dispatch depth boundary", async () => {
+    if (process.platform === "win32") {
+      return;
+    }
+    const { runCommand, sendInvokeResult, sendNodeEvent } = createInvokeSpies({
+      runCommand: vi.fn(async () => {
+        throw new Error("runCommand should not be called for depth-boundary shell wrappers");
+      }),
+    });
+
+    await withTempApprovalsHome({
+      approvals: createAllowlistOnMissApprovals({
+        agents: {
+          main: {
+            allowlist: [{ pattern: "/usr/bin/env" }],
+          },
+        },
+      }),
+      run: async ({ tempHome }) => {
+        const marker = path.join(tempHome, "depth4-pwned.txt");
+        await runSystemInvoke({
+          preferMacAppExecHost: false,
+          command: buildNestedEnvShellCommand({
+            depth: 4,
+            payload: `echo PWNED > ${marker}`,
+          }),
+          security: "allowlist",
+          ask: "on-miss",
+          runCommand,
+          sendInvokeResult,
+          sendNodeEvent,
+        });
+        expect(fs.existsSync(marker)).toBe(false);
+      },
+    });
+
+    expect(runCommand).not.toHaveBeenCalled();
+    expectApprovalRequiredDenied({ sendNodeEvent, sendInvokeResult });
+  });
+
   it("denies nested env shell payloads when wrapper depth is exceeded", async () => {
     if (process.platform === "win32") {
       return;