diff --git a/CHANGELOG.md b/CHANGELOG.md
index 310d438e4db..533e75d7297 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -303,6 +303,7 @@ Docs: https://docs.openclaw.ai
 - Nodes/system.run PowerShell wrapper parsing: treat `pwsh`/`powershell` `-EncodedCommand` forms as shell-wrapper payloads so allowlist mode still requires approval instead of falling back to plain argv analysis. Thanks @tdjackey for reporting.
 - Control UI/auth error reporting: map generic browser `Fetch failed` websocket close errors back to actionable gateway auth messages (`gateway token mismatch`, `authentication failed`, `retry later`) so dashboard disconnects stop hiding credential problems. Landed from contributor PR #28608 by @KimGLee. Thanks @KimGLee.
 - 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.
 
 ## 2026.3.2
 
diff --git a/src/infra/exec-approvals-allow-always.test.ts b/src/infra/exec-approvals-allow-always.test.ts
index 4a3c53c7614..b2d091e986e 100644
--- a/src/infra/exec-approvals-allow-always.test.ts
+++ b/src/infra/exec-approvals-allow-always.test.ts
@@ -302,4 +302,21 @@ describe("resolveAllowAlwaysPatterns", () => {
       persistedPattern: echo,
     });
   });
+
+  it("does not persist comment-tailed payload paths that never execute", () => {
+    if (process.platform === "win32") {
+      return;
+    }
+    const dir = makeTempDir();
+    const benign = makeExecutable(dir, "benign");
+    makeExecutable(dir, "payload");
+    const env = makePathEnv(dir);
+    expectAllowAlwaysBypassBlocked({
+      dir,
+      firstCommand: `${benign} warmup # && payload`,
+      secondCommand: "payload",
+      env,
+      persistedPattern: benign,
+    });
+  });
 });
diff --git a/src/infra/exec-approvals-analysis.ts b/src/infra/exec-approvals-analysis.ts
index d67256e891c..f55f7c56c53 100644
--- a/src/infra/exec-approvals-analysis.ts
+++ b/src/infra/exec-approvals-analysis.ts
@@ -59,6 +59,17 @@ function isEscapedLineContinuation(next: string | undefined): next is string {
   return next === "\n" || next === "\r";
 }
 
+function isShellCommentStart(source: string, index: number): boolean {
+  if (source[index] !== "#") {
+    return false;
+  }
+  if (index === 0) {
+    return true;
+  }
+  const prev = source[index - 1];
+  return Boolean(prev && /\s/.test(prev));
+}
+
 function splitShellPipeline(command: string): { ok: boolean; reason?: string; segments: string[] } {
   type HeredocSpec = {
     delimiter: string;
@@ -246,6 +257,9 @@ function splitShellPipeline(command: string): { ok: boolean; reason?: string; se
       emptySegment = false;
       continue;
     }
+    if (isShellCommentStart(command, i)) {
+      break;
+    }
 
     if ((ch === "\n" || ch === "\r") && pendingHeredocs.length > 0) {
       inHeredocBody = true;
@@ -501,6 +515,9 @@ export function splitCommandChainWithOperators(command: string): ShellChainPart[
       buf += ch;
       continue;
     }
+    if (isShellCommentStart(command, i)) {
+      break;
+    }
 
     if (ch === "&" && next === "&") {
       if (!pushPart("&&")) {
diff --git a/src/utils/shell-argv.ts b/src/utils/shell-argv.ts
index d62b9b08e81..3f75dfa22ef 100644
--- a/src/utils/shell-argv.ts
+++ b/src/utils/shell-argv.ts
@@ -59,6 +59,10 @@ export function splitShellArgs(raw: string): string[] | null {
       inDouble = true;
       continue;
     }
+    // In POSIX shells, "#" starts a comment only when it begins a word.
+    if (ch === "#" && buf.length === 0) {
+      break;
+    }
     if (/\s/.test(ch)) {
       pushToken();
       continue;
diff --git a/src/utils/utils-misc.test.ts b/src/utils/utils-misc.test.ts
index 88f0c311ae2..ae3d09d150e 100644
--- a/src/utils/utils-misc.test.ts
+++ b/src/utils/utils-misc.test.ts
@@ -106,4 +106,10 @@ describe("splitShellArgs", () => {
     expect(splitShellArgs(`echo "oops`)).toBeNull();
     expect(splitShellArgs(`echo 'oops`)).toBeNull();
   });
+
+  it("stops at unquoted shell comments but keeps quoted hashes literal", () => {
+    expect(splitShellArgs(`echo hi # comment && whoami`)).toEqual(["echo", "hi"]);
+    expect(splitShellArgs(`echo "hi # still-literal"`)).toEqual(["echo", "hi # still-literal"]);
+    expect(splitShellArgs(`echo hi#tail`)).toEqual(["echo", "hi#tail"]);
+  });
 });