diff --git a/deploy/files/usr/local/libexec/left4me/left4me-overlay b/deploy/files/usr/local/libexec/left4me/left4me-overlay
index c01a5af..74ad954 100644
--- a/deploy/files/usr/local/libexec/left4me/left4me-overlay
+++ b/deploy/files/usr/local/libexec/left4me/left4me-overlay
@@ -55,6 +55,31 @@ def die(msg: str) -> None:
     sys.exit(1)
 
 
+def _is_mountpoint(
+    path: str | Path,
+    mountinfo_path: str = "/proc/self/mountinfo",
+) -> bool:
+    """Reliable mount-point check that handles same-fs bind mounts.
+
+    `os.path.ismount()` compares `st_dev` of the path against its parent;
+    bind mounts on the same underlying filesystem share `st_dev` with their
+    parent, so `os.path.ismount()` returns False for them. The idmap binds
+    we install on `runtime/<n>/idmap/<basename>` are exactly that case.
+    Read /proc/self/mountinfo (field 5 is the mount point) for a check
+    that works regardless of mount type. The override is for tests only.
+    """
+    abs_path = os.fspath(Path(path).resolve())
+    try:
+        with open(mountinfo_path, "r", encoding="utf-8") as f:
+            for line in f:
+                fields = line.split()
+                if len(fields) >= 5 and fields[4] == abs_path:
+                    return True
+    except OSError:
+        pass
+    return False
+
+
 def _lookup_uid(username: str) -> tuple[int, int]:
     """Return (uid, gid) for *username*, dying with a clear message if missing."""
     try:
@@ -256,7 +281,7 @@ def cmd_mount(name: str) -> None:
                 idmap_dir.mkdir(mode=0o700, exist_ok=True)
                 idmap_target.mkdir(mode=0o700, exist_ok=True)
 
-            if not os.path.ismount(idmap_target) or \
+            if not _is_mountpoint(idmap_target) or \
                     os.environ.get("LEFT4ME_OVERLAY_PRINT_ONLY") == "1":
                 # --map-users / --map-groups argument format:
                 #   <on-disk-uid>:<in-mount-uid>:<count>
@@ -359,10 +384,11 @@ def cmd_umount(name: str) -> None:
 
     # Unwind idmap bind mounts, then remove the idmap directory.  Each bind
     # is only umounted if it is still a mountpoint (idempotent across partial
-    # teardowns).
+    # teardowns). _is_mountpoint reads /proc/self/mountinfo because
+    # os.path.ismount misses same-fs bind mounts.
     for bind_umount_argv in bind_umount_argvs:
         target = Path(bind_umount_argv[-1])
-        if os.path.ismount(target):
+        if _is_mountpoint(target):
             subprocess.run(bind_umount_argv, check=True)
     shutil.rmtree(idmap_dir, ignore_errors=True)
 
diff --git a/l4d2host/tests/test_overlay_helper.py b/l4d2host/tests/test_overlay_helper.py
index 6beda12..8044eb0 100644
--- a/l4d2host/tests/test_overlay_helper.py
+++ b/l4d2host/tests/test_overlay_helper.py
@@ -303,3 +303,47 @@ def test_rejects_upperdir_with_fuseoverlayfs_xattr(tmp_path: Path) -> None:
     result = _run(["mount", "alpha"], tmp_path)
     assert result.returncode != 0
     assert "fuse-overlayfs xattr" in result.stderr
+
+
+def _load_helper_module():
+    """Import the helper script as a Python module for unit testing internals.
+
+    The helper file has no .py extension, so importlib needs an explicit
+    SourceFileLoader rather than auto-detection.
+    """
+    import importlib.util
+    from importlib.machinery import SourceFileLoader
+    loader = SourceFileLoader("left4me_overlay", str(HELPER_SOURCE))
+    spec = importlib.util.spec_from_loader("left4me_overlay", loader)
+    assert spec is not None
+    module = importlib.util.module_from_spec(spec)
+    loader.exec_module(module)
+    return module
+
+
+def test_is_mountpoint_detects_same_fs_bind_mount(tmp_path: Path) -> None:
+    """_is_mountpoint reads /proc/self/mountinfo so it works for same-fs bind mounts.
+
+    Regression: os.path.ismount() compares st_dev against the parent, which
+    silently returns False for same-fs bind mounts. The idmap binds we install
+    on runtime/<n>/idmap/<basename> are exactly that case, so an ismount-based
+    check skipped umount on stop and re-bound on top on start — accumulating
+    mount-table entries across stop/start cycles.
+    """
+    helper = _load_helper_module()
+
+    target = tmp_path / "some-bind"
+    target.mkdir()
+    abs_target = str(target.resolve())
+
+    mountinfo = tmp_path / "fake-mountinfo"
+    # mountinfo column 5 is the mountpoint; build a minimal line that exercises
+    # the parse without depending on the rest of the format.
+    mountinfo.write_text(
+        f"42 1 0:30 / {abs_target} rw,relatime - tmpfs tmpfs rw\n"
+        f"43 1 0:31 / /some/other/path rw,relatime - tmpfs tmpfs rw\n"
+    )
+
+    assert helper._is_mountpoint(target, str(mountinfo)) is True
+    assert helper._is_mountpoint(tmp_path / "not-a-mount", str(mountinfo)) is False
+    assert helper._is_mountpoint(target, str(tmp_path / "no-such-file")) is False