diff --git a/tests/tools/test_hardline_blocklist.py b/tests/tools/test_hardline_blocklist.py
index 669c867dc..7e6f918b8 100644
--- a/tests/tools/test_hardline_blocklist.py
+++ b/tests/tools/test_hardline_blocklist.py
@@ -31,6 +31,18 @@ _HARDLINE_BLOCK = [
     # rm -rf targeting root / system dirs / home
     "rm -rf /",
     "rm -rf /*",
+    # Shell-equivalent spellings of "rm -rf /": repeated slashes and
+    # current/parent-dir segments all collapse back to root, so they must
+    # hit the hardline floor too (regression: these used to slip through the
+    # root pattern's target group and fall to the softer DANGEROUS_PATTERNS
+    # rule, which --yolo / approvals.mode=off / cron approve-mode bypass).
+    "rm -rf //",
+    "rm -rf /.",
+    "rm -rf /./",
+    "rm -rf /..",
+    "rm -rf //*",
+    "rm -fr /./",
+    "ls && rm -rf //",
     "rm -rf /home",
     "rm -rf /home/*",
     "rm -rf /etc",
@@ -329,6 +341,37 @@ def test_yolo_env_var_cannot_bypass_hardline(clean_session, monkeypatch):
         assert r2.get("hardline") is True
 
 
+def test_root_collapse_forms_cannot_bypass_hardline(clean_session, monkeypatch):
+    """Shell-equivalent spellings of "rm -rf /" stay blocked under yolo.
+
+    "//", "/.", "/./", "/..", "//*" all collapse to the root filesystem in
+    the shell. They previously matched only the softer DANGEROUS_PATTERNS
+    rule, which yolo bypasses — leaving the hardline floor open to a full
+    root wipe under --yolo / approvals.mode=off / cron approve-mode.
+    """
+    monkeypatch.setenv("HERMES_YOLO_MODE", "1")
+
+    for cmd in ["rm -rf //", "rm -rf /.", "rm -rf /./", "rm -rf /..", "rm -rf //*"]:
+        is_hl, _ = detect_hardline_command(cmd)
+        assert is_hl, f"{cmd!r} should be hardline-blocked"
+        result = check_all_command_guards(cmd, "local")
+        assert result["approved"] is False, f"yolo leaked hardline on {cmd!r}"
+        assert result.get("hardline") is True
+
+
+def test_root_collapse_pattern_leaves_real_paths_alone(clean_session):
+    """The broadened root token must not over-match real trailing segments.
+
+    A path with a real component after the root-collapse prefix (/tmp,
+    /home/user/x, /.ssh, ./build) is recoverable-or-legitimate and must NOT
+    be pulled onto the hardline floor by the "collapse to /" broadening.
+    """
+    for cmd in ["rm -rf /tmp", "rm -rf /home/user/x", "rm -rf /.ssh",
+                "rm -rf /.config", "rm -rf ./build", "rm -rf /opt/foo"]:
+        is_hl, _ = detect_hardline_command(cmd)
+        assert not is_hl, f"{cmd!r} must not be hardline-blocked (over-match)"
+
+
 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 92b6fb3ad..e7c1cecba 100644
--- a/tools/approval.py
+++ b/tools/approval.py
@@ -367,7 +367,18 @@ HARDLINE_PATTERNS = [
     # `${HOME}` brace form and quoted paths (`rm -rf "/"`, `rm -rf "$HOME"`)
     # are handled via _hardline_rm_path so the floor cannot be bypassed with
     # the ordinary quoting/brace shell idioms.
-    (_RM_FLAG_PREFIX + _hardline_rm_path(r'/|/\*|/ \*'), "recursive delete of root filesystem"),
+    #
+    # The path token matches any root-anchored path whose components collapse
+    # back to "/" in the shell: a bare "/", repeated slashes ("//"), and
+    # "."/".." current/parent segments ("/.", "/./", "/..") all resolve to
+    # root, optionally followed by a trailing glob ("/*", "//*"). The earlier
+    # "/|/\*|/ \*" form only caught the literal "/" / "/*" spellings, so
+    # `rm -rf //`, `rm -rf /.`, `rm -rf /./`, `rm -rf /..` and `rm -rf //*`
+    # silently slipped the hardline floor and executed under --yolo /
+    # approvals.mode=off / cron approve-mode. A trailing real segment
+    # (e.g. "/tmp", "/home", "/.ssh") still fails to match here and stays
+    # with the softer DANGEROUS_PATTERNS / system-directory rules.
+    (_RM_FLAG_PREFIX + _hardline_rm_path(r'/[/.]*\**'), "recursive delete of root filesystem"),
     (_RM_FLAG_PREFIX + _hardline_rm_path(_HARDLINE_SYSTEM_DIRS), "recursive delete of system directory"),
     (_RM_FLAG_PREFIX + _hardline_rm_path(r'(?:~|\$\{?HOME\}?)(?:/?|/\*)?'), "recursive delete of home directory"),
     # Filesystem format