diff --git a/tests/tools/test_hardline_blocklist.py b/tests/tools/test_hardline_blocklist.py
index 7e6f918b8ca..e084e61fe8f 100644
--- a/tests/tools/test_hardline_blocklist.py
+++ b/tests/tools/test_hardline_blocklist.py
@@ -118,6 +118,23 @@ _HARDLINE_BLOCK = [
     "exec shutdown",
     "nohup reboot",
     "setsid poweroff",
+    # Bare subshell `(cmd)` and brace-group `{ cmd; }` openers put the trigger
+    # at a real command position, so they must hit the floor just like `$(…)`.
+    # These slipped through before the quote-aware command-start tokenizer
+    # learned to recognize `(` / `{` (issue: (reboot) walked past --yolo).
+    "(reboot)",
+    "( reboot )",
+    "(shutdown -h now)",
+    "(poweroff)",
+    "(halt)",
+    "(init 0)",
+    "(systemctl reboot)",
+    "(sudo reboot)",
+    "{ reboot; }",
+    "{ shutdown -h now; }",
+    "{ poweroff; }",
+    "true && (reboot)",
+    "echo hi; { reboot; }",
 ]
 
 
@@ -225,6 +242,18 @@ _DATA_ARG_NOT_A_COMMAND = [
     'echo "rm -rf /"',
     'printf "%s" "rm -rf /"',
     'gh issue comment 1 --body "the fix blocks rm -rf //"',
+    # A `(` or `{` INSIDE a quoted argument is prose, not a subshell/brace
+    # opener — the trigger word after it is data. Naively adding `(` / `{` to
+    # the flat command-position class blocked these (it broke our own
+    # `gh pr create --title "…(reboot)…"` workflow); the quote-aware tokenizer
+    # must leave them alone.
+    'gh pr create --title "block (reboot) spellings"',
+    'git commit -m "(rm -rf /) note"',
+    'echo "(reboot)"',
+    'echo "{ reboot; }"',
+    "echo '(poweroff)'",
+    "echo '{ rm -rf /; }'",
+    'find . -name "*(reboot)*"',
 ]
 
 
@@ -249,6 +278,11 @@ _COMMAND_POSITION_ROOT_WIPES = [
     "$(rm -rf /)",
     "`rm -rf /`",
     'echo "$(rm -rf /)"',
+    # Bare subshell / brace-group openers are real command positions too.
+    "(rm -rf /)",
+    "{ rm -rf /; }",
+    "(rm -rf ~)",
+    "(sudo rm -rf /)",
 ]
 
 
@@ -372,6 +406,47 @@ def test_root_collapse_pattern_leaves_real_paths_alone(clean_session):
         assert not is_hl, f"{cmd!r} must not be hardline-blocked (over-match)"
 
 
+def test_subshell_brace_group_cannot_bypass_hardline(clean_session, monkeypatch):
+    """Wrapping a catastrophic command in `(…)` or `{ …; }` must not bypass
+    the floor, even under yolo. `(reboot)` / `{ shutdown -h now; }` walked
+    straight past the guard before the command-start tokenizer recognized the
+    subshell and brace-group openers.
+    """
+    monkeypatch.setenv("HERMES_YOLO_MODE", "1")
+
+    for cmd in ["(reboot)", "( reboot )", "(shutdown -h now)", "(poweroff)",
+                "(systemctl reboot)", "(init 0)", "(sudo reboot)",
+                "{ reboot; }", "{ shutdown -h now; }", "{ poweroff; }",
+                "(rm -rf /)", "{ rm -rf /; }", "(rm -rf ~)",
+                "true && (reboot)", "echo hi; { reboot; }"]:
+        r1 = check_dangerous_command(cmd, "local")
+        assert r1["approved"] is False, f"yolo leaked hardline on {cmd!r} (check_dangerous_command)"
+        assert r1.get("hardline") is True
+
+        r2 = check_all_command_guards(cmd, "local")
+        assert r2["approved"] is False, f"yolo leaked hardline on {cmd!r} (check_all_command_guards)"
+        assert r2.get("hardline") is True
+
+
+def test_quoted_paren_brace_prose_not_blocked_under_yolo(clean_session, monkeypatch):
+    """A `(` / `{` inside a quoted argument is prose, not a command opener.
+
+    Regression guard: naively adding `(` / `{` to the flat command-position
+    class blocked ordinary quoted arguments — including our own
+    `gh pr create --title "…(reboot)…"` workflow. The quote-aware tokenizer
+    must leave quoted text untouched, so these stay runnable.
+    """
+    monkeypatch.setenv("HERMES_YOLO_MODE", "1")
+
+    for cmd in ['gh pr create --title "block (reboot) spellings"',
+                'git commit -m "(rm -rf /) note"',
+                'echo "(reboot)"', 'echo "{ reboot; }"',
+                "echo '(poweroff)'", 'find . -name "*(reboot)*"']:
+        assert detect_hardline_command(cmd)[0] is False, (
+            f"quoted prose false-positived on the hardline floor: {cmd!r}"
+        )
+
+
 def test_line_continuation_root_wipe_cannot_bypass_hardline(clean_session, monkeypatch):
     """A line-continuation root wipe must stay blocked even under yolo.
 
diff --git a/tools/approval.py b/tools/approval.py
index e7c1cecba66..2797f4a7ad5 100644
--- a/tools/approval.py
+++ b/tools/approval.py
@@ -1158,6 +1158,17 @@ def _iter_shell_command_starts(command: str):
             starts.append(i + 2)
             i += 2
             continue
+        # Bare subshell `(cmd)` and brace group `{ cmd; }` openers begin a new
+        # command context, just like `;` or `$(`. We only reach this branch
+        # OUTSIDE any quote (the quote arms above `continue` first), so a `(`
+        # or `{` sitting inside a quoted argument — `--title "block (reboot)"`,
+        # `echo "{ reboot; }"` — never registers a command start. That is the
+        # whole reason this lives in the quote-aware tokenizer instead of the
+        # flat `_CMDPOS` regex, which cannot tell quoted text from real syntax.
+        if ch in ("(", "{"):
+            starts.append(i + 1)
+            i += 1
+            continue
         if ch == ";":
             starts.append(i + 1)
             i += 1
@@ -1190,6 +1201,29 @@ def _iter_shell_command_starts(command: str):
             yield start
 
 
+def _mark_command_starts(command: str) -> str:
+    """Insert a newline before each real (quote-aware) command start.
+
+    ``\\n`` is already a ``_CMDPOS`` separator, so this rewrites subshell
+    ``(cmd)`` and brace-group ``{ cmd; }`` openers — which the flat pattern
+    class deliberately omits — into a form the anchored hardline/dangerous
+    patterns recognize, WITHOUT the quoted-prose false positives that adding
+    ``(`` / ``{`` to ``_CMDPOS`` would cause. Starts inside quotes are never
+    produced by ``_iter_shell_command_starts``, so quoted arguments such as
+    ``--title "block (reboot)"`` are left exactly as-is.
+    """
+    # Collect the (whitespace-skipped) start offsets, drop 0 (already anchored
+    # by ``^``), and splice a newline in front of each — right-to-left so the
+    # earlier offsets stay valid as we mutate.
+    offsets = sorted(o for o in _iter_shell_command_starts(command) if o > 0)
+    if not offsets:
+        return command
+    out = command
+    for offset in reversed(offsets):
+        out = out[:offset] + "\n" + out[offset:]
+    return out
+
+
 def _iter_shell_command_word_spans(command: str):
     """Yield command-position words that may be executable names."""
     for command_start in _iter_shell_command_starts(command):
@@ -1236,6 +1270,21 @@ def _command_detection_variants(command: str):
     normalized = _normalize_command_for_detection(command)
     seen = {normalized}
     yield normalized
+    # Subshell `(cmd)` and brace-group `{ cmd; }` openers put `cmd` at a real
+    # command position, but the flat `_CMDPOS`-anchored patterns can't see it:
+    # their start-position class deliberately omits `(`/`{` because a bare
+    # regex cannot tell `(reboot)` (real subshell) from `--title "(reboot)"`
+    # (quoted prose) — adding them there regresses ordinary quoted arguments.
+    # Instead, reconstruct the command with a newline (already a `_CMDPOS`
+    # separator) inserted at each command start the QUOTE-AWARE tokenizer
+    # found. Openers inside quotes never yield a start, so quoted prose is
+    # untouched, while `(reboot)` / `{ shutdown -h now; }` now anchor. This
+    # covers every `_CMDPOS` rule (shutdown/reboot/init/systemctl/telinit and
+    # the rm root/home/system floor) in one place.
+    marked = _mark_command_starts(normalized)
+    if marked != normalized and marked not in seen:
+        seen.add(marked)
+        yield marked
     # Shell quoting/escaping can spell a dangerous executable name in pieces
     # (for example r\m or r''m). Keep that deobfuscation scoped to command
     # words so similarly shaped arguments do not become false positives.