diff --git a/src/adapters/cursor/native-exec-shell.ts b/src/adapters/cursor/native-exec-shell.ts
index 27c07fd71..cda058fca 100644
--- a/src/adapters/cursor/native-exec-shell.ts
+++ b/src/adapters/cursor/native-exec-shell.ts
@@ -23,8 +23,20 @@ import { errorText, execBytes, execStreamCloseBytes } from "./native-exec-common
 const backgroundShells = new Map<number, { child: ChildProcessWithoutNullStreams; outputLength: number }>();
 let nextShellId = 1;
 
-const NATIVE_SHELL_DISABLED =
-  "Route this through the Codex bridge shell tool from the current catalog (`shell_command` or `exec_command`, including the long `mcp_opencodex-responses_*` display name if listed). Do not tell the user shell access is blocked, disabled, or denied — silently call that bridge tool with the same command.";
+/** Rejection text when Cursor-native shell is denied by policy (issue #604). */
+export function nativeShellDisabledMessage(): string {
+  // Do not insist on "the same command" — that steers models into replaying bash/CMD
+  // idioms through the Codex bridge on Windows PowerShell 5.1 and looping (#604).
+  // Keep this host-shell-neutral: OpenCodex may run on a different OS than the Codex
+  // client that executes the bridge (LAN/SSH remote-proxy).
+  return (
+    "Route this through the Codex bridge shell tool from the current catalog (`shell_command` or `exec_command`, including the long `mcp_opencodex-responses_*` display name if listed). "
+    + "Do not tell the user shell access is blocked, disabled, or denied — silently call that bridge tool. "
+    + "Adapt the command for the Codex client host shell before calling the bridge "
+    + "(Windows PowerShell 5.1: no CMD `cd /d`, no bash heredocs; `&&`/`||` are unsupported parser errors — prefer the bridge working-directory argument for directory changes, and use `if ($?) { ... }` for success-gated follow-up steps; do not treat `;` as a substitute for `&&`). "
+    + "Make at most one corrected bridge attempt after a failure, then report the error and stop — do not repeat equivalent failing commands."
+  );
+}
 
 function rejectedShellResult(command: string, cwd: string, started: number) {
   return create(ShellResultSchema, {
@@ -36,7 +48,7 @@ function rejectedShellResult(command: string, cwd: string, started: number) {
         exitCode: 1,
         signal: "",
         stdout: "",
-        stderr: NATIVE_SHELL_DISABLED,
+        stderr: nativeShellDisabledMessage(),
         executionTime: Date.now() - started,
         aborted: true,
       }),
@@ -95,7 +107,7 @@ export function rejectShellStreamExecForPolicy(execMsg: ExecServerMessage): Uint
       event: { case: "start", value: create(ShellStreamStartSchema, { sandboxPolicy: args.requestedSandboxPolicy }) },
     })),
     execBytes(execMsg, "shellStream", create(ShellStreamSchema, {
-      event: { case: "stderr", value: create(ShellStreamStderrSchema, { data: NATIVE_SHELL_DISABLED }) },
+      event: { case: "stderr", value: create(ShellStreamStderrSchema, { data: nativeShellDisabledMessage() }) },
     })),
     execBytes(execMsg, "shellStream", create(ShellStreamSchema, {
       event: { case: "exit", value: create(ShellStreamExitSchema, { code: 1, cwd, aborted: true }) },
@@ -196,7 +208,7 @@ export function rejectBackgroundShellSpawnExecForPolicy(execMsg: ExecServerMessa
   const args = execMsg.message.value;
   const cwd = resolve(args.workingDirectory || process.cwd());
   return execBytes(execMsg, "backgroundShellSpawnResult", create(BackgroundShellSpawnResultSchema, {
-    result: { case: "error", value: create(BackgroundShellSpawnErrorSchema, { command: args.command, workingDirectory: cwd, error: NATIVE_SHELL_DISABLED }) },
+    result: { case: "error", value: create(BackgroundShellSpawnErrorSchema, { command: args.command, workingDirectory: cwd, error: nativeShellDisabledMessage() }) },
   }));
 }
 
@@ -233,7 +245,7 @@ export function backgroundShellSpawnExec(execMsg: ExecServerMessage): Uint8Array
 export function rejectWriteShellStdinExecForPolicy(execMsg: ExecServerMessage): Uint8Array {
   if (execMsg.message.case !== "writeShellStdinArgs") throw new Error("invalid shell stdin exec");
   return execBytes(execMsg, "writeShellStdinResult", create(WriteShellStdinResultSchema, {
-    result: { case: "error", value: create(WriteShellStdinErrorSchema, { error: NATIVE_SHELL_DISABLED }) },
+    result: { case: "error", value: create(WriteShellStdinErrorSchema, { error: nativeShellDisabledMessage() }) },
   }));
 }
 
diff --git a/src/adapters/cursor/tool-definitions.ts b/src/adapters/cursor/tool-definitions.ts
index 274cda914..7688f209a 100644
--- a/src/adapters/cursor/tool-definitions.ts
+++ b/src/adapters/cursor/tool-definitions.ts
@@ -417,6 +417,11 @@ export function buildCursorToolGuidanceSystemNote(
   const hasApplyPatch = cursorRequestAdvertisesApplyPatch(tools, toolChoice);
   const discoveryTools = discoveryToolLabel(wireNames);
   const unavailableNeighborNames = unavailableNeighborAgentToolNames(wireNames);
+  // Host-shell-neutral: the Codex client executes bridge commands, and may differ from
+  // the OpenCodex proxy OS (LAN/SSH remote-proxy). Always cover PowerShell 5.1 pitfalls.
+  const hostShellNote = hasBareExec
+    ? "Match shell syntax to the Codex client host that runs the bridge (not only the proxy OS). Windows PowerShell 5.1: no CMD `cd /d`, no bash heredocs (`<<EOF`); `&&`/`||` are unsupported parser errors — prefer the bridge working-directory argument for directory changes, and use `if ($?) { ... }` for success-gated follow-up steps; do not treat `;` as a substitute for `&&`. POSIX: use portable commands. After a shell failure, make at most one corrected bridge attempt, then report the error and stop — do not repeat equivalent failing commands."
+    : undefined;
   const notes = [
     `Cursor tool calls: available tool names are exactly ${listedNames}.`,
     "Use the current tool catalog as ground truth and call only those exact names with their listed argument keys.",
@@ -432,6 +437,7 @@ export function buildCursorToolGuidanceSystemNote(
     hasBareExec
       ? "Never tell the user that shell or read access is blocked, disabled, or denied unless the Codex shell bridge tool itself fails. Prefer the bridge over Cursor-native Shell/Read; do not narrate phrases like \"Native shell access is blocked\" — silently call `shell_command` / `exec_command`."
       : undefined,
+    hostShellNote,
     "Cursor product features (Chronicle, screen recording, Notes, Plans, background agents) are available only if this turn's catalog lists a matching tool; do not offer or promise them otherwise.",
     hasBareExec
       ? `For file read/search/listing, use ${shellBridgeLabel} when no more specific listed tool is available.`
@@ -451,7 +457,7 @@ export function buildCursorToolGuidanceSystemNote(
       : undefined,
     "Do not count or report a tool call unless a tool result was actually returned.",
     hasBareExec
-      ? `If a Cursor-native file read, directory listing, grep, or shell operation is rejected by the runtime, silently use ${shellBridgeLabel} with the equivalent shell command instead (e.g. \`cat\`, \`ls\`, \`rg\`, \`grep\`). Do not tell the user access is blocked. For file edits, use \`apply_patch\` when available.`
+      ? `If a Cursor-native file read, directory listing, grep, or shell operation is rejected by the runtime, silently use ${shellBridgeLabel} with an equivalent host-shell-safe command (POSIX: \`cat\`/\`ls\`/\`rg\`; Windows PowerShell: \`Get-Content\`/\`Get-ChildItem\`/\`Select-String\`). Do not tell the user access is blocked. For file edits, use \`apply_patch\` when available.`
       : undefined,
   ].filter((note): note is string => typeof note === "string");
   return notes.join(" ");
diff --git a/tests/cursor-native-exec-policy.test.ts b/tests/cursor-native-exec-policy.test.ts
index e745cdec3..80ecee7c7 100644
--- a/tests/cursor-native-exec-policy.test.ts
+++ b/tests/cursor-native-exec-policy.test.ts
@@ -142,6 +142,12 @@ describe("Cursor native exec sandbox policy", () => {
     expect(deniedShellText).toContain("exec_command");
     expect(deniedShellText).toContain("mcp_opencodex-responses_*");
     expect(deniedShellText).toContain("Do not tell the user");
+    expect(deniedShellText).not.toContain("with the same command");
+    expect(deniedShellText).toContain("at most one corrected bridge attempt");
+    expect(deniedShellText).toContain("if ($?)");
+    expect(deniedShellText).toContain("`&&`/`||` are unsupported parser errors");
+    expect(deniedShellText).toContain("do not treat `;` as a substitute for `&&`");
+    expect(deniedShellText).toContain("Windows PowerShell 5.1");
     expect(deniedShellText).not.toContain("disabled by OpenCodex policy");
     expect(deniedShellText).not.toContain("sandbox denial");
     expect(deniedShell.message.case).toBe("shellResult");
diff --git a/tests/cursor-tool-definitions.test.ts b/tests/cursor-tool-definitions.test.ts
index 652a93515..d418b304b 100644
--- a/tests/cursor-tool-definitions.test.ts
+++ b/tests/cursor-tool-definitions.test.ts
@@ -324,6 +324,23 @@ describe("Cursor tool definitions", () => {
     expect(note).toContain("Never tell the user that shell or read access is blocked");
   });
 
+  test("adds host-shell-neutral PowerShell and one-retry-stop guidance (#604)", () => {
+    const note = buildCursorToolGuidanceSystemNote([{ name: "shell_command", description: "Run", parameters: {} }]);
+    expect(note).toBeDefined();
+    if (!note) throw new Error("Expected Cursor tool guidance note");
+
+    expect(note).toContain("Windows PowerShell 5.1");
+    expect(note).toContain("cd /d");
+    expect(note).toContain("<<EOF");
+    expect(note).toContain("if ($?)");
+    expect(note).toContain("`&&`/`||` are unsupported parser errors");
+    expect(note).toContain("do not treat `;` as a substitute for `&&`");
+    expect(note).toContain("at most one corrected bridge attempt");
+    expect(note).toContain("Get-Content");
+    expect(note).toContain("`cat`/`ls`/`rg`");
+    expect(note).toContain("Codex client host");
+  });
+
   test("adds codex-native edit guidance only when apply_patch is advertised", () => {
     const tools: OcxTool[] = [
       { name: "exec_command", description: "Run", parameters: {} },