diff --git a/CHANGELOG.md b/CHANGELOG.md
index e9b5c9a99f5..a6515638991 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -43,6 +43,7 @@ Docs: https://docs.openclaw.ai
 - Security/agent: reject public spawned-run lineage fields and keep workspace inheritance on the internal spawned-session path so external `agent` callers can no longer override the gateway workspace boundary. (`GHSA-2rqg-gjgv-84jm`)(#43801) Thanks @tdjackey and @vincentkoc.
 - Security/session_status: enforce sandbox session-tree visibility and shared agent-to-agent access guards before reading or mutating target session state, so sandboxed subagents can no longer inspect parent session metadata or write parent model overrides via `session_status`. (`GHSA-wcxr-59v9-rxr8`)(#43754) Thanks @tdjackey and @vincentkoc.
 - Security/agent tools: mark `nodes` as explicitly owner-only and document/test that `canvas` remains a shared trusted-operator surface unless a real boundary bypass exists.
+- Security/exec approvals: fail closed for Ruby approval flows that use `-r`, `--require`, or `-I` so approval-backed commands no longer bind only the main script while extra local code-loading flags remain outside the reviewed file snapshot.
 - Security/device pairing: cap issued and verified device-token scopes to each paired device's approved scope baseline so stale or overbroad tokens cannot exceed approved access. (`GHSA-2pwv-x786-56f8`)(#43686) Thanks @tdjackey and @vincentkoc.
 - Models/secrets: enforce source-managed SecretRef markers in generated `models.json` so runtime-resolved provider secrets are not persisted when runtime projection is skipped. (#43759) Thanks @joshavant.
 - Security/WebSocket preauth: shorten unauthenticated handshake retention and reject oversized pre-auth frames before application-layer parsing to reduce pre-pairing exposure on unsupported public deployments. (`GHSA-jv4g-m82p-2j93`)(#44089) (`GHSA-xwx2-ppv2-wx98`)(#44089) Thanks @ez-lbz and @vincentkoc.
diff --git a/src/node-host/invoke-system-run-plan.test.ts b/src/node-host/invoke-system-run-plan.test.ts
index 010e7b5e4ef..438163d1d66 100644
--- a/src/node-host/invoke-system-run-plan.test.ts
+++ b/src/node-host/invoke-system-run-plan.test.ts
@@ -548,6 +548,52 @@ describe("hardenApprovedExecutionPaths", () => {
     });
   });
 
+  it("rejects ruby require preloads that approval cannot bind completely", () => {
+    withFakeRuntimeBin({
+      binName: "ruby",
+      run: () => {
+        const tmp = fs.mkdtempSync(path.join(os.tmpdir(), "openclaw-ruby-require-"));
+        try {
+          fs.writeFileSync(path.join(tmp, "safe.rb"), 'puts "SAFE"\n');
+          const prepared = buildSystemRunApprovalPlan({
+            command: ["ruby", "-r", "attacker", "./safe.rb"],
+            cwd: tmp,
+          });
+          expect(prepared).toEqual({
+            ok: false,
+            message:
+              "SYSTEM_RUN_DENIED: approval cannot safely bind this interpreter/runtime command",
+          });
+        } finally {
+          fs.rmSync(tmp, { recursive: true, force: true });
+        }
+      },
+    });
+  });
+
+  it("rejects ruby load-path flags that can redirect module resolution after approval", () => {
+    withFakeRuntimeBin({
+      binName: "ruby",
+      run: () => {
+        const tmp = fs.mkdtempSync(path.join(os.tmpdir(), "openclaw-ruby-load-path-"));
+        try {
+          fs.writeFileSync(path.join(tmp, "safe.rb"), 'puts "SAFE"\n');
+          const prepared = buildSystemRunApprovalPlan({
+            command: ["ruby", "-I.", "./safe.rb"],
+            cwd: tmp,
+          });
+          expect(prepared).toEqual({
+            ok: false,
+            message:
+              "SYSTEM_RUN_DENIED: approval cannot safely bind this interpreter/runtime command",
+          });
+        } finally {
+          fs.rmSync(tmp, { recursive: true, force: true });
+        }
+      },
+    });
+  });
+
   it("rejects shell payloads that hide mutable interpreter scripts", () => {
     withFakeRuntimeBin({
       binName: "node",
diff --git a/src/node-host/invoke-system-run-plan.ts b/src/node-host/invoke-system-run-plan.ts
index afcc2963e9d..867ea9f696f 100644
--- a/src/node-host/invoke-system-run-plan.ts
+++ b/src/node-host/invoke-system-run-plan.ts
@@ -134,6 +134,8 @@ const NODE_OPTIONS_WITH_FILE_VALUE = new Set([
   "--require",
 ]);
 
+const RUBY_UNSAFE_APPROVAL_FLAGS = new Set(["-I", "-r", "--require"]);
+
 const POSIX_SHELL_OPTIONS_WITH_VALUE = new Set([
   "--init-file",
   "--rcfile",
@@ -604,6 +606,33 @@ function resolveDenoRunScriptOperandIndex(params: {
   });
 }
 
+function hasRubyUnsafeApprovalFlag(argv: string[]): boolean {
+  let afterDoubleDash = false;
+  for (let i = 1; i < argv.length; i += 1) {
+    const token = argv[i]?.trim() ?? "";
+    if (!token) {
+      continue;
+    }
+    if (afterDoubleDash) {
+      return false;
+    }
+    if (token === "--") {
+      afterDoubleDash = true;
+      continue;
+    }
+    if (token === "-I" || token === "-r") {
+      return true;
+    }
+    if (token.startsWith("-I") || token.startsWith("-r")) {
+      return true;
+    }
+    if (RUBY_UNSAFE_APPROVAL_FLAGS.has(token.toLowerCase())) {
+      return true;
+    }
+  }
+  return false;
+}
+
 function isMutableScriptRunner(executable: string): boolean {
   return GENERIC_MUTABLE_SCRIPT_RUNNERS.has(executable) || isInterpreterLikeSafeBin(executable);
 }
@@ -642,6 +671,9 @@ function resolveMutableFileOperandIndex(argv: string[], cwd: string | undefined)
       return unwrapped.baseIndex + denoIndex;
     }
   }
+  if (executable === "ruby" && hasRubyUnsafeApprovalFlag(unwrapped.argv)) {
+    return null;
+  }
   if (!isMutableScriptRunner(executable)) {
     return null;
   }