diff --git a/hermes_cli/backup.py b/hermes_cli/backup.py
index cae165b908..51437c03a6 100644
--- a/hermes_cli/backup.py
+++ b/hermes_cli/backup.py
@@ -36,6 +36,7 @@ _EXCLUDED_DIRS = {
     "__pycache__",      # bytecode caches — regenerated on import
     ".git",             # nested git dirs (profiles shouldn't have these, but safety)
     "node_modules",     # js deps if website/ somehow leaks in
+    "backups",          # prior auto-backups — don't nest backups exponentially
 }
 
 # File-name suffixes to skip
@@ -683,3 +684,138 @@ def run_quick_backup(args) -> None:
         print(f"  Restore with: /snapshot restore {snap_id}")
     else:
         print("No state files found to snapshot.")
+
+
+# ---------------------------------------------------------------------------
+# Pre-update auto-backup
+# ---------------------------------------------------------------------------
+
+_PRE_UPDATE_BACKUPS_DIR = "backups"
+_PRE_UPDATE_PREFIX = "pre-update-"
+_PRE_UPDATE_DEFAULT_KEEP = 5
+
+
+def _pre_update_backup_dir(hermes_home: Optional[Path] = None) -> Path:
+    home = hermes_home or get_hermes_home()
+    return home / _PRE_UPDATE_BACKUPS_DIR
+
+
+def _prune_pre_update_backups(backup_dir: Path, keep: int) -> int:
+    """Remove oldest pre-update backups beyond the keep limit.
+
+    Returns the number of files deleted.  Only touches files matching
+    ``pre-update-*.zip`` so hand-made zips dropped in the same directory
+    are never touched.
+    """
+    if keep < 0:
+        keep = 0
+    if not backup_dir.exists():
+        return 0
+
+    backups = sorted(
+        (p for p in backup_dir.iterdir()
+         if p.is_file() and p.name.startswith(_PRE_UPDATE_PREFIX) and p.suffix.lower() == ".zip"),
+        key=lambda p: p.name,
+        reverse=True,
+    )
+
+    deleted = 0
+    for p in backups[keep:]:
+        try:
+            p.unlink()
+            deleted += 1
+        except OSError as exc:
+            logger.warning("Failed to prune backup %s: %s", p.name, exc)
+
+    return deleted
+
+
+def create_pre_update_backup(
+    hermes_home: Optional[Path] = None,
+    keep: int = _PRE_UPDATE_DEFAULT_KEEP,
+) -> Optional[Path]:
+    """Create a full zip backup of HERMES_HOME under ``backups/``.
+
+    Mirrors :func:`run_backup` (same exclusion rules, same SQLite safe-copy)
+    but writes to ``<HERMES_HOME>/backups/pre-update-<timestamp>.zip`` and
+    auto-prunes old pre-update backups.
+
+    Returns the path to the created zip, or ``None`` if no files were
+    found or the backup could not be created.  Never raises — the caller
+    (``hermes update``) should continue even if the backup fails.
+    """
+    hermes_root = hermes_home or get_default_hermes_root()
+    if not hermes_root.is_dir():
+        return None
+
+    backup_dir = _pre_update_backup_dir(hermes_root)
+    try:
+        backup_dir.mkdir(parents=True, exist_ok=True)
+    except OSError as exc:
+        logger.warning("Could not create pre-update backup dir %s: %s", backup_dir, exc)
+        return None
+
+    stamp = datetime.now().strftime("%Y-%m-%d-%H%M%S")
+    out_path = backup_dir / f"{_PRE_UPDATE_PREFIX}{stamp}.zip"
+
+    # Collect files (same logic as run_backup, minus the chatty progress prints)
+    files_to_add: list[tuple[Path, Path]] = []
+    try:
+        for dirpath, dirnames, filenames in os.walk(hermes_root, followlinks=False):
+            dp = Path(dirpath)
+            # Prune excluded directories in-place so os.walk doesn't descend
+            dirnames[:] = [d for d in dirnames if d not in _EXCLUDED_DIRS]
+
+            for fname in filenames:
+                fpath = dp / fname
+                try:
+                    rel = fpath.relative_to(hermes_root)
+                except ValueError:
+                    continue
+
+                if _should_exclude(rel):
+                    continue
+
+                # Skip the output zip itself if it already exists
+                try:
+                    if fpath.resolve() == out_path.resolve():
+                        continue
+                except (OSError, ValueError):
+                    pass
+
+                files_to_add.append((fpath, rel))
+    except OSError as exc:
+        logger.warning("Pre-update backup: walk failed: %s", exc)
+        return None
+
+    if not files_to_add:
+        return None
+
+    try:
+        with zipfile.ZipFile(out_path, "w", zipfile.ZIP_DEFLATED, compresslevel=6) as zf:
+            for abs_path, rel_path in files_to_add:
+                try:
+                    if abs_path.suffix == ".db":
+                        with tempfile.NamedTemporaryFile(suffix=".db", delete=False) as tmp:
+                            tmp_db = Path(tmp.name)
+                        try:
+                            if _safe_copy_db(abs_path, tmp_db):
+                                zf.write(tmp_db, arcname=str(rel_path))
+                        finally:
+                            tmp_db.unlink(missing_ok=True)
+                    else:
+                        zf.write(abs_path, arcname=str(rel_path))
+                except (PermissionError, OSError, ValueError) as exc:
+                    logger.debug("Skipping %s in pre-update backup: %s", rel_path, exc)
+                    continue
+    except OSError as exc:
+        logger.warning("Pre-update backup: zip write failed: %s", exc)
+        # Best-effort cleanup of partial file
+        try:
+            out_path.unlink(missing_ok=True)
+        except OSError:
+            pass
+        return None
+
+    _prune_pre_update_backups(backup_dir, keep=keep)
+    return out_path
diff --git a/hermes_cli/config.py b/hermes_cli/config.py
index e061fff62c..f0777b80aa 100644
--- a/hermes_cli/config.py
+++ b/hermes_cli/config.py
@@ -1037,6 +1037,19 @@ DEFAULT_CONFIG = {
         "seen": {},
     },
 
+    # ``hermes update`` behaviour.
+    "updates": {
+        # Run a full ``hermes backup``-style zip of HERMES_HOME before every
+        # ``hermes update``.  Backups land in ``<HERMES_HOME>/backups/`` and
+        # can be restored with ``hermes import <path>``.  Set to false to
+        # skip the backup entirely; use the ``--no-backup`` flag on a single
+        # update invocation to override just that run.
+        "pre_update_backup": True,
+        # How many pre-update backup zips to retain.  Older ones are pruned
+        # automatically after each successful backup.
+        "backup_keep": 5,
+    },
+
     # Config schema version - bump this when adding new required fields
     "_config_version": 22,
 }
diff --git a/hermes_cli/main.py b/hermes_cli/main.py
index ca0bef6106..b838fb9e0e 100644
--- a/hermes_cli/main.py
+++ b/hermes_cli/main.py
@@ -6142,6 +6142,90 @@ def _ensure_fhs_path_guard() -> None:
         print("    (reload your shell or run 'source ~/.bashrc' to pick it up)")
 
 
+def _run_pre_update_backup(args) -> None:
+    """Create a full zip backup of HERMES_HOME before running the update.
+
+    Gated on ``updates.pre_update_backup`` in config (default true).  The
+    ``--no-backup`` flag on ``hermes update`` overrides it for one run.
+    Never raises — a backup failure should not block the update itself.
+    """
+    # CLI flag wins over config
+    if getattr(args, "no_backup", False):
+        print("◆ Pre-update backup: skipped (--no-backup)")
+        print()
+        return
+
+    try:
+        from hermes_cli.config import load_config
+        cfg = load_config()
+    except Exception as exc:
+        logging.getLogger(__name__).debug("Could not load config for pre-update backup: %s", exc)
+        cfg = {}
+
+    updates_cfg = cfg.get("updates", {}) if isinstance(cfg, dict) else {}
+    enabled = updates_cfg.get("pre_update_backup", True)
+    keep = updates_cfg.get("backup_keep", 5)
+
+    if not enabled:
+        print("◆ Pre-update backup: disabled (updates.pre_update_backup=false in config.yaml)")
+        print()
+        return
+
+    try:
+        from hermes_cli.backup import create_pre_update_backup
+    except Exception as exc:
+        print(f"⚠ Pre-update backup: could not load backup module ({exc}); continuing update.")
+        print()
+        return
+
+    print("◆ Creating pre-update backup...")
+    t0 = _time.monotonic()
+    try:
+        out_path = create_pre_update_backup(keep=int(keep))
+    except Exception as exc:  # defensive — helper already swallows, but just in case
+        print(f"  ⚠ Backup failed: {exc}")
+        print("  Continuing with update.")
+        print()
+        return
+
+    elapsed = _time.monotonic() - t0
+
+    if out_path is None:
+        print("  ⚠ Backup skipped (no files found or write failed); continuing update.")
+        print()
+        return
+
+    try:
+        size_bytes = out_path.stat().st_size
+    except OSError:
+        size_bytes = 0
+
+    # Human-readable size
+    size_str = f"{size_bytes} B"
+    for unit in ("KB", "MB", "GB"):
+        if size_bytes < 1024:
+            break
+        size_bytes /= 1024
+        size_str = f"{size_bytes:.1f} {unit}"
+
+    # Render path using display_hermes_home so the user sees ~/.hermes/...
+    try:
+        from hermes_constants import get_hermes_home, display_hermes_home
+        home = get_hermes_home()
+        try:
+            display_path = f"{display_hermes_home()}/{out_path.relative_to(home)}"
+        except ValueError:
+            display_path = str(out_path)
+    except Exception:
+        display_path = str(out_path)
+
+    print(f"  Saved:    {display_path} ({size_str}, {elapsed:.1f}s)")
+    print(f"  Restore:  hermes import {out_path}")
+    print(f"  Disable:  set updates.pre_update_backup: false in config.yaml")
+    print(f"            (or pass --no-backup on a single update)")
+    print()
+
+
 def cmd_update(args):
     """Update Hermes Agent to the latest version.
 
@@ -6184,6 +6268,10 @@ def _cmd_update_impl(args, gateway_mode: bool):
     print("⚕ Updating Hermes Agent...")
     print()
 
+    # Pre-update backup — runs before any git/file mutation so users can
+    # always roll back to the exact state they had before this update.
+    _run_pre_update_backup(args)
+
     # Try git-based update first, fall back to ZIP download on Windows
     # when git file I/O is broken (antivirus, NTFS filter drivers, etc.)
     use_zip_update = False
@@ -9577,6 +9665,12 @@ Examples:
         default=False,
         help="Check whether an update is available without installing anything",
     )
+    update_parser.add_argument(
+        "--no-backup",
+        action="store_true",
+        default=False,
+        help="Skip the pre-update backup for this run (overrides updates.pre_update_backup)",
+    )
     update_parser.set_defaults(func=cmd_update)
 
     # =========================================================================
diff --git a/tests/hermes_cli/test_backup.py b/tests/hermes_cli/test_backup.py
index 805862cd80..f12e4757b2 100644
--- a/tests/hermes_cli/test_backup.py
+++ b/tests/hermes_cli/test_backup.py
@@ -1218,3 +1218,189 @@ class TestQuickSnapshot:
         snap_id = create_quick_snapshot(hermes_home=hermes_home)
         # Other state still present → snapshot succeeds.
         assert snap_id is not None
+
+# ---------------------------------------------------------------------------
+# Pre-update backup (hermes update safety net)
+# ---------------------------------------------------------------------------
+
+class TestPreUpdateBackup:
+    """Tests for create_pre_update_backup — the auto-backup ``hermes update``
+    runs before touching anything."""
+
+    @pytest.fixture
+    def hermes_home(self, tmp_path):
+        root = tmp_path / ".hermes"
+        root.mkdir()
+        _make_hermes_tree(root)
+        return root
+
+    def test_creates_backup_under_backups_dir(self, hermes_home):
+        from hermes_cli.backup import create_pre_update_backup
+        out = create_pre_update_backup(hermes_home=hermes_home)
+        assert out is not None
+        assert out.exists()
+        assert out.parent == hermes_home / "backups"
+        assert out.name.startswith("pre-update-")
+        assert out.suffix == ".zip"
+
+    def test_backup_contents_match_full_backup(self, hermes_home):
+        """Pre-update backup should include the same user data that
+        ``hermes backup`` would, and should exclude the same directories."""
+        from hermes_cli.backup import create_pre_update_backup
+        out = create_pre_update_backup(hermes_home=hermes_home)
+        assert out is not None
+        with zipfile.ZipFile(out) as zf:
+            names = set(zf.namelist())
+        # User data present
+        assert "config.yaml" in names
+        assert ".env" in names
+        assert "sessions/abc123.json" in names
+        assert "skills/my-skill/SKILL.md" in names
+        assert "profiles/coder/config.yaml" in names
+        # hermes-agent repo excluded
+        assert not any(n.startswith("hermes-agent/") for n in names)
+        # __pycache__ excluded
+        assert not any("__pycache__" in n for n in names)
+        # pid files excluded
+        assert "gateway.pid" not in names
+
+    def test_does_not_recurse_into_prior_backups(self, hermes_home):
+        """The ``backups/`` directory must be excluded so that each backup
+        doesn't grow exponentially by including all prior backups."""
+        from hermes_cli.backup import create_pre_update_backup
+        # First backup
+        out1 = create_pre_update_backup(hermes_home=hermes_home)
+        assert out1 is not None
+        # Second backup — must not include the first
+        out2 = create_pre_update_backup(hermes_home=hermes_home)
+        assert out2 is not None
+        with zipfile.ZipFile(out2) as zf:
+            names = zf.namelist()
+        assert not any(n.startswith("backups/") for n in names), (
+            f"Pre-update backup recursed into backups/ — leaked: "
+            f"{[n for n in names if n.startswith('backups/')]}"
+        )
+
+    def test_rotation_keeps_only_n(self, hermes_home):
+        """After more than ``keep`` backups are created, older ones are
+        pruned automatically."""
+        import time as _t
+        from hermes_cli.backup import create_pre_update_backup
+
+        created = []
+        for _ in range(5):
+            out = create_pre_update_backup(hermes_home=hermes_home, keep=3)
+            created.append(out)
+            _t.sleep(1.05)  # ensure distinct seconds in timestamp
+
+        remaining = sorted(
+            p.name for p in (hermes_home / "backups").iterdir()
+            if p.name.startswith("pre-update-")
+        )
+        assert len(remaining) == 3
+        # Oldest two should have been pruned
+        assert created[0].name not in remaining
+        assert created[1].name not in remaining
+        # Newest three should remain
+        assert created[4].name in remaining
+
+    def test_rotation_preserves_manual_files(self, hermes_home):
+        """Hand-dropped zips in ``backups/`` must not be touched by
+        rotation — it only prunes files matching ``pre-update-*.zip``."""
+        import time as _t
+        from hermes_cli.backup import create_pre_update_backup
+
+        (hermes_home / "backups").mkdir(exist_ok=True)
+        manual = hermes_home / "backups" / "my-manual.zip"
+        manual.write_bytes(b"manual backup")
+
+        for _ in range(5):
+            create_pre_update_backup(hermes_home=hermes_home, keep=2)
+            _t.sleep(1.05)
+
+        assert manual.exists(), "Manual backup zip was incorrectly pruned"
+
+    def test_returns_none_if_root_missing(self, tmp_path):
+        from hermes_cli.backup import create_pre_update_backup
+        assert create_pre_update_backup(hermes_home=tmp_path / "does-not-exist") is None
+
+
+class TestRunPreUpdateBackup:
+    """Tests for the ``_run_pre_update_backup`` wrapper in main.py —
+    covers config gate, ``--no-backup`` flag, and user-facing output."""
+
+    @pytest.fixture
+    def hermes_home(self, tmp_path, monkeypatch):
+        root = tmp_path / ".hermes"
+        root.mkdir()
+        _make_hermes_tree(root)
+        # Point HERMES_HOME at the temp dir so config + backup paths resolve here
+        monkeypatch.setenv("HERMES_HOME", str(root))
+        # Make Path.home() point at tmp_path for anything that uses it
+        monkeypatch.setattr(Path, "home", lambda: tmp_path)
+        # Bust caches for hermes_cli.config + hermes_constants so they pick up HERMES_HOME
+        for mod in list(__import__("sys").modules.keys()):
+            if mod.startswith("hermes_cli.config") or mod == "hermes_constants":
+                del __import__("sys").modules[mod]
+        return root
+
+    def test_default_enabled_creates_backup(self, hermes_home, capsys):
+        from hermes_cli.main import _run_pre_update_backup
+        _run_pre_update_backup(Namespace(no_backup=False))
+        out = capsys.readouterr().out
+        assert "Creating pre-update backup" in out
+        assert "Saved:" in out
+        assert "Restore:" in out
+        assert "hermes import" in out
+        assert "Disable:" in out
+        # Actual backup was created
+        backups = list((hermes_home / "backups").glob("pre-update-*.zip"))
+        assert len(backups) == 1
+
+    def test_no_backup_flag_skips(self, hermes_home, capsys):
+        from hermes_cli.main import _run_pre_update_backup
+        _run_pre_update_backup(Namespace(no_backup=True))
+        out = capsys.readouterr().out
+        assert "skipped (--no-backup)" in out
+        assert "Creating pre-update backup" not in out
+        # No backup written
+        assert not (hermes_home / "backups").exists() or not list(
+            (hermes_home / "backups").glob("pre-update-*.zip")
+        )
+
+    def test_config_disabled_skips(self, hermes_home, capsys):
+        import yaml
+        (hermes_home / "config.yaml").write_text(yaml.safe_dump({
+            "_config_version": 22,
+            "updates": {"pre_update_backup": False},
+        }))
+        # Ensure config module re-reads
+        import sys as _sys
+        for mod in list(_sys.modules.keys()):
+            if mod.startswith("hermes_cli.config"):
+                del _sys.modules[mod]
+
+        from hermes_cli.main import _run_pre_update_backup
+        _run_pre_update_backup(Namespace(no_backup=False))
+        out = capsys.readouterr().out
+        assert "disabled" in out
+        assert "updates.pre_update_backup=false" in out
+        assert not list((hermes_home / "backups").glob("pre-update-*.zip")) \
+            if (hermes_home / "backups").exists() else True
+
+    def test_cli_flag_overrides_enabled_config(self, hermes_home, capsys):
+        """--no-backup wins even when config says pre_update_backup: true."""
+        import yaml
+        (hermes_home / "config.yaml").write_text(yaml.safe_dump({
+            "_config_version": 22,
+            "updates": {"pre_update_backup": True},
+        }))
+        import sys as _sys
+        for mod in list(_sys.modules.keys()):
+            if mod.startswith("hermes_cli.config"):
+                del _sys.modules[mod]
+
+        from hermes_cli.main import _run_pre_update_backup
+        _run_pre_update_backup(Namespace(no_backup=True))
+        out = capsys.readouterr().out
+        assert "skipped (--no-backup)" in out