diff --git a/src/permission/command.test.ts b/src/permission/command.test.ts
index da41e3492..68e94b465 100644
--- a/src/permission/command.test.ts
+++ b/src/permission/command.test.ts
@@ -56,6 +56,28 @@ describe("splitChainedCommand heredocs", () => {
   });
 });
 
+describe("splitChainedCommand lone-& bypass (CL-7781)", () => {
+  // A `&` with no trailing space still backgrounds the preceding command —
+  // treating it as a redirect token lets a second command hide behind a
+  // standing grant for the benign head. Only a redirect-bound `&` (after
+  // `>`/`<`, or opening `&>`/`&>>`) stays attached to its command.
+  const cases: { command: string; segments: string[] }[] = [
+    { command: "a &b", segments: ["a", "b"] },
+    { command: "a & b", segments: ["a", "b"] },
+    { command: "a &>f", segments: ["a &>f"] },
+    { command: "a 2>&1", segments: ["a 2>&1"] },
+    { command: "a >&2", segments: ["a >&2"] },
+    { command: "a <&-", segments: ["a <&-"] },
+    { command: "a&&b", segments: ["a", "b"] },
+    { command: "a &&b", segments: ["a", "b"] },
+  ];
+  for (const { command, segments } of cases) {
+    test(`splits ${JSON.stringify(command)} into ${segments.length} segment(s)`, () => {
+      expect(splitChainedCommand(command)).toEqual(segments);
+    });
+  }
+});
+
 describe("splitChainedCommand redirect and background fragments", () => {
   // A bare digit (or "-") after a chain separator is not, by itself, evidence
   // of a stray redirect remnant — it may be a genuine, distinct command. Only
diff --git a/src/permission/gate.test.ts b/src/permission/gate.test.ts
index 1b25bd575..1bcb68637 100644
--- a/src/permission/gate.test.ts
+++ b/src/permission/gate.test.ts
@@ -115,6 +115,40 @@ describe("preGrantGuardReason / isRequestCoveredByGrant guard parity", () => {
   });
 });
 
+describe("lone-& bypass at the gate (CL-7781)", () => {
+  // A standing grant for a benign head must not auto-allow a payload hidden
+  // behind a `&` with no trailing space. Per-segment coverage means the
+  // hidden second segment has no matching grant and the request stays
+  // uncovered (the gate prompts) — same as the spaced form.
+  const cwd = mkdtempSync(join(tmpdir(), "gate-lone-amp-"));
+  const isRestricted = createPathRestriction(
+    cwd,
+    createWorktreeRootsProvider(cwd),
+  ).isRestricted;
+  const workspace = { resolvedCwd: cwd, roots: [] as string[] };
+  const grant: Approval = { tool: "run_shell", pattern: "bun test *" };
+  const covered = (subject: string): boolean =>
+    isRequestCoveredByGrant(
+      { tool: "run_shell", action: "Run", subject, scopes: [], cwd },
+      grant,
+      undefined,
+      isRestricted,
+      workspace,
+    );
+
+  test("unspaced &payload is not covered by a grant for the head", () => {
+    expect(covered("bun test x &touch pwn")).toBe(false);
+  });
+
+  test("spaced & payload is not covered by a grant for the head", () => {
+    expect(covered("bun test x & touch pwn")).toBe(false);
+  });
+
+  test("the benign head alone stays covered", () => {
+    expect(covered("bun test x")).toBe(true);
+  });
+});
+
 // Relative path tokens rebind to the request's process cwd before the gate's
 // restriction closure judges them, so a sub-agent worktree's relative targets
 // match what the shell will open. Absolute paths still pass through the
diff --git a/src/shell/command-segments.ts b/src/shell/command-segments.ts
index a4ec34353..2939d2fb1 100644
--- a/src/shell/command-segments.ts
+++ b/src/shell/command-segments.ts
@@ -113,12 +113,14 @@ export function splitChainedCommand(command: string): string[] {
       i++;
       continue;
     }
-    // `&` participates in a redirect when it opens a bash combined redirect
-    // (`&>file`) or duplicates a fd after `>`/`<` (`2>&1`, `<&-`). In those
-    // positions it is not a background operator and must not split the chain —
-    // otherwise `bun run build 2>&1` fragments into a real command and a stray
-    // `1`, and the operator gets a separate approval prompt for "1".
-    if (ch === "&" && isRedirectAmpersand(next)) {
+    // `&` is redirect-bound only by its neighbours: a preceding `>`/`<`
+    // (fd duplication: `2>&1`, `>&2`, `<&-`) or an immediately following `>`
+    // (combined redirect: `&>file`, `&>>file`). Any other `&` — including one
+    // with no trailing space (`a &b`) — is the background operator and must
+    // split the chain; otherwise `bun run build 2>&1` fragments into a real
+    // command and a stray `1`, and the operator gets a separate approval
+    // prompt for "1".
+    if (ch === "&" && isRedirectAmpersand(previousNonSpace(current), next)) {
       current += ch;
       continue;
     }
@@ -215,9 +217,22 @@ function unwrapGroup(segment: string): string | null {
   return null;
 }
 
-// `&` is the background operator when it stands alone as a word — followed by
-// whitespace or end of input. Anywhere else it is part of a redirect token:
-// `2>&1`, `<&-`, `&>file`.
-function isRedirectAmpersand(next: string | undefined): boolean {
-  return !(next === undefined || next === " " || next === "\t");
+// The closest non-space character already scanned into the current segment,
+// or undefined at the start of a segment. `&` consults this (not the
+// following character) to decide whether it is redirect-bound.
+function previousNonSpace(current: string): string | undefined {
+  const trimmed = current.trimEnd();
+  return trimmed.length > 0 ? trimmed[trimmed.length - 1] : undefined;
+}
+
+// `&` is redirect-bound only when the previous non-space character is `>` or
+// `<` (fd duplication or close: `2>&1`, `>&2`, `<&-`), or when `&` is
+// immediately followed by `>` (combined redirect: `&>file`, `&>>file`).
+// Everything else is the background operator — a chain boundary.
+function isRedirectAmpersand(
+  prev: string | undefined,
+  next: string | undefined,
+): boolean {
+  if (next === ">") return true;
+  return prev === ">" || prev === "<";
 }