diff --git a/gateway/run.py b/gateway/run.py
index d5aeec247f..4715955bed 100644
--- a/gateway/run.py
+++ b/gateway/run.py
@@ -771,7 +771,7 @@ class GatewayRunner:
         _known_commands = {"new", "reset", "help", "status", "stop", "model",
                           "personality", "retry", "undo", "sethome", "set-home",
                           "compress", "usage", "insights", "reload-mcp", "reload_mcp",
-                          "update", "title", "resume", "provider"}
+                          "update", "title", "resume", "provider", "rollback"}
         if command and command in _known_commands:
             await self.hooks.emit(f"command:{command}", {
                 "platform": source.platform.value if source.platform else "",
@@ -830,6 +830,9 @@ class GatewayRunner:
 
         if command == "resume":
             return await self._handle_resume_command(event)
+
+        if command == "rollback":
+            return await self._handle_rollback_command(event)
         
         # Skill slash commands: /skill-name loads the skill and sends to agent
         if command:
@@ -1400,6 +1403,7 @@ class GatewayRunner:
             "`/resume [name]` — Resume a previously-named session",
             "`/usage` — Show token usage for this session",
             "`/insights [days]` — Show usage insights and analytics",
+            "`/rollback [number]` — List or restore filesystem checkpoints",
             "`/reload-mcp` — Reload MCP servers from config",
             "`/update` — Update Hermes Agent to the latest version",
             "`/help` — Show this message",
@@ -1746,6 +1750,65 @@ class GatewayRunner:
             f"Cron jobs and cross-platform messages will be delivered here."
         )
     
+    async def _handle_rollback_command(self, event: MessageEvent) -> str:
+        """Handle /rollback command — list or restore filesystem checkpoints."""
+        from tools.checkpoint_manager import CheckpointManager, format_checkpoint_list
+
+        # Read checkpoint config from config.yaml
+        cp_cfg = {}
+        try:
+            import yaml as _y
+            _cfg_path = _hermes_home / "config.yaml"
+            if _cfg_path.exists():
+                with open(_cfg_path, encoding="utf-8") as _f:
+                    _data = _y.safe_load(_f) or {}
+                cp_cfg = _data.get("checkpoints", {})
+                if isinstance(cp_cfg, bool):
+                    cp_cfg = {"enabled": cp_cfg}
+        except Exception:
+            pass
+
+        if not cp_cfg.get("enabled", False):
+            return (
+                "Checkpoints are not enabled.\n"
+                "Enable in config.yaml:\n```\ncheckpoints:\n  enabled: true\n```"
+            )
+
+        mgr = CheckpointManager(
+            enabled=True,
+            max_snapshots=cp_cfg.get("max_snapshots", 50),
+        )
+
+        cwd = os.getenv("MESSAGING_CWD", str(Path.home()))
+        arg = event.get_command_args().strip()
+
+        if not arg:
+            checkpoints = mgr.list_checkpoints(cwd)
+            return format_checkpoint_list(checkpoints, cwd)
+
+        # Restore by number or hash
+        checkpoints = mgr.list_checkpoints(cwd)
+        if not checkpoints:
+            return f"No checkpoints found for {cwd}"
+
+        target_hash = None
+        try:
+            idx = int(arg) - 1
+            if 0 <= idx < len(checkpoints):
+                target_hash = checkpoints[idx]["hash"]
+            else:
+                return f"Invalid checkpoint number. Use 1-{len(checkpoints)}."
+        except ValueError:
+            target_hash = arg
+
+        result = mgr.restore(cwd, target_hash)
+        if result["success"]:
+            return (
+                f"✅ Restored to checkpoint {result['restored_to']}: {result['reason']}\n"
+                f"A pre-rollback snapshot was saved automatically."
+            )
+        return f"❌ {result['error']}"
+
     async def _handle_compress_command(self, event: MessageEvent) -> str:
         """Handle /compress command -- manually compress conversation context."""
         source = event.source
diff --git a/hermes_cli/main.py b/hermes_cli/main.py
index 8f0f16ff98..20d70fcb64 100644
--- a/hermes_cli/main.py
+++ b/hermes_cli/main.py
@@ -489,6 +489,7 @@ def cmd_chat(args):
         "query": args.query,
         "resume": getattr(args, "resume", None),
         "worktree": getattr(args, "worktree", False),
+        "checkpoints": getattr(args, "checkpoints", False),
     }
     # Filter out None values
     kwargs = {k: v for k, v in kwargs.items() if v is not None}
@@ -1927,6 +1928,12 @@ For more help on a command:
         default=False,
         help="Run in an isolated git worktree (for parallel agents on the same repo)"
     )
+    chat_parser.add_argument(
+        "--checkpoints",
+        action="store_true",
+        default=False,
+        help="Enable filesystem checkpoints before destructive file operations (use /rollback to restore)"
+    )
     chat_parser.set_defaults(func=cmd_chat)
 
     # =========================================================================
diff --git a/run_agent.py b/run_agent.py
index cd6be25531..a5bb21af51 100644
--- a/run_agent.py
+++ b/run_agent.py
@@ -185,6 +185,8 @@ class AIAgent:
         honcho_session_key: str = None,
         iteration_budget: "IterationBudget" = None,
         fallback_model: Dict[str, Any] = None,
+        checkpoints_enabled: bool = False,
+        checkpoint_max_snapshots: int = 50,
     ):
         """
         Initialize the AI Agent.
@@ -486,6 +488,13 @@ class AIAgent:
         # Cached system prompt -- built once per session, only rebuilt on compression
         self._cached_system_prompt: Optional[str] = None
         
+        # Filesystem checkpoint manager (transparent — not a tool)
+        from tools.checkpoint_manager import CheckpointManager
+        self._checkpoint_mgr = CheckpointManager(
+            enabled=checkpoints_enabled,
+            max_snapshots=checkpoint_max_snapshots,
+        )
+        
         # SQLite session store (optional -- provided by CLI or gateway)
         self._session_db = session_db
         if self._session_db:
@@ -2706,6 +2715,18 @@ class AIAgent:
                 except Exception as cb_err:
                     logging.debug(f"Tool progress callback error: {cb_err}")
 
+            # Checkpoint: snapshot working dir before file-mutating tools
+            if function_name in ("write_file", "patch") and self._checkpoint_mgr.enabled:
+                try:
+                    file_path = function_args.get("path", "")
+                    if file_path:
+                        work_dir = self._checkpoint_mgr.get_working_dir_for_path(file_path)
+                        self._checkpoint_mgr.ensure_checkpoint(
+                            work_dir, f"before {function_name}"
+                        )
+                except Exception:
+                    pass  # never block tool execution
+
             tool_start_time = time.time()
 
             if function_name == "todo":
@@ -3215,6 +3236,9 @@ class AIAgent:
         self.clear_interrupt()
         
         while api_call_count < self.max_iterations and self.iteration_budget.remaining > 0:
+            # Reset per-turn checkpoint dedup so each iteration can take one snapshot
+            self._checkpoint_mgr.new_turn()
+
             # Check for interrupt request (e.g., user sent new message)
             if self._interrupt_requested:
                 interrupted = True
diff --git a/tests/tools/test_checkpoint_manager.py b/tests/tools/test_checkpoint_manager.py
new file mode 100644
index 0000000000..fc8479aca2
--- /dev/null
+++ b/tests/tools/test_checkpoint_manager.py
@@ -0,0 +1,385 @@
+"""Tests for tools/checkpoint_manager.py — CheckpointManager."""
+
+import os
+import json
+import shutil
+import pytest
+from pathlib import Path
+from unittest.mock import patch
+
+from tools.checkpoint_manager import (
+    CheckpointManager,
+    _shadow_repo_path,
+    _init_shadow_repo,
+    _run_git,
+    _git_env,
+    _dir_file_count,
+    format_checkpoint_list,
+    DEFAULT_EXCLUDES,
+    CHECKPOINT_BASE,
+)
+
+
+# =========================================================================
+# Fixtures
+# =========================================================================
+
+@pytest.fixture()
+def work_dir(tmp_path):
+    """Temporary working directory."""
+    d = tmp_path / "project"
+    d.mkdir()
+    (d / "main.py").write_text("print('hello')\\n")
+    (d / "README.md").write_text("# Project\\n")
+    return d
+
+
+@pytest.fixture()
+def checkpoint_base(tmp_path):
+    """Isolated checkpoint base — never writes to ~/.hermes/."""
+    return tmp_path / "checkpoints"
+
+
+@pytest.fixture()
+def mgr(work_dir, checkpoint_base, monkeypatch):
+    """CheckpointManager with redirected checkpoint base."""
+    monkeypatch.setattr("tools.checkpoint_manager.CHECKPOINT_BASE", checkpoint_base)
+    return CheckpointManager(enabled=True, max_snapshots=50)
+
+
+@pytest.fixture()
+def disabled_mgr(checkpoint_base, monkeypatch):
+    """Disabled CheckpointManager."""
+    monkeypatch.setattr("tools.checkpoint_manager.CHECKPOINT_BASE", checkpoint_base)
+    return CheckpointManager(enabled=False)
+
+
+# =========================================================================
+# Shadow repo path
+# =========================================================================
+
+class TestShadowRepoPath:
+    def test_deterministic(self, work_dir, checkpoint_base, monkeypatch):
+        monkeypatch.setattr("tools.checkpoint_manager.CHECKPOINT_BASE", checkpoint_base)
+        p1 = _shadow_repo_path(str(work_dir))
+        p2 = _shadow_repo_path(str(work_dir))
+        assert p1 == p2
+
+    def test_different_dirs_different_paths(self, tmp_path, checkpoint_base, monkeypatch):
+        monkeypatch.setattr("tools.checkpoint_manager.CHECKPOINT_BASE", checkpoint_base)
+        p1 = _shadow_repo_path(str(tmp_path / "a"))
+        p2 = _shadow_repo_path(str(tmp_path / "b"))
+        assert p1 != p2
+
+    def test_under_checkpoint_base(self, work_dir, checkpoint_base, monkeypatch):
+        monkeypatch.setattr("tools.checkpoint_manager.CHECKPOINT_BASE", checkpoint_base)
+        p = _shadow_repo_path(str(work_dir))
+        assert str(p).startswith(str(checkpoint_base))
+
+
+# =========================================================================
+# Shadow repo init
+# =========================================================================
+
+class TestShadowRepoInit:
+    def test_creates_git_repo(self, work_dir, checkpoint_base, monkeypatch):
+        monkeypatch.setattr("tools.checkpoint_manager.CHECKPOINT_BASE", checkpoint_base)
+        shadow = _shadow_repo_path(str(work_dir))
+        err = _init_shadow_repo(shadow, str(work_dir))
+        assert err is None
+        assert (shadow / "HEAD").exists()
+
+    def test_no_git_in_project_dir(self, work_dir, checkpoint_base, monkeypatch):
+        monkeypatch.setattr("tools.checkpoint_manager.CHECKPOINT_BASE", checkpoint_base)
+        shadow = _shadow_repo_path(str(work_dir))
+        _init_shadow_repo(shadow, str(work_dir))
+        assert not (work_dir / ".git").exists()
+
+    def test_has_exclude_file(self, work_dir, checkpoint_base, monkeypatch):
+        monkeypatch.setattr("tools.checkpoint_manager.CHECKPOINT_BASE", checkpoint_base)
+        shadow = _shadow_repo_path(str(work_dir))
+        _init_shadow_repo(shadow, str(work_dir))
+        exclude = shadow / "info" / "exclude"
+        assert exclude.exists()
+        content = exclude.read_text()
+        assert "node_modules/" in content
+        assert ".env" in content
+
+    def test_has_workdir_file(self, work_dir, checkpoint_base, monkeypatch):
+        monkeypatch.setattr("tools.checkpoint_manager.CHECKPOINT_BASE", checkpoint_base)
+        shadow = _shadow_repo_path(str(work_dir))
+        _init_shadow_repo(shadow, str(work_dir))
+        workdir_file = shadow / "HERMES_WORKDIR"
+        assert workdir_file.exists()
+        assert str(work_dir.resolve()) in workdir_file.read_text()
+
+    def test_idempotent(self, work_dir, checkpoint_base, monkeypatch):
+        monkeypatch.setattr("tools.checkpoint_manager.CHECKPOINT_BASE", checkpoint_base)
+        shadow = _shadow_repo_path(str(work_dir))
+        err1 = _init_shadow_repo(shadow, str(work_dir))
+        err2 = _init_shadow_repo(shadow, str(work_dir))
+        assert err1 is None
+        assert err2 is None
+
+
+# =========================================================================
+# CheckpointManager — disabled
+# =========================================================================
+
+class TestDisabledManager:
+    def test_ensure_checkpoint_returns_false(self, disabled_mgr, work_dir):
+        assert disabled_mgr.ensure_checkpoint(str(work_dir)) is False
+
+    def test_new_turn_works(self, disabled_mgr):
+        disabled_mgr.new_turn()  # should not raise
+
+
+# =========================================================================
+# CheckpointManager — taking checkpoints
+# =========================================================================
+
+class TestTakeCheckpoint:
+    def test_first_checkpoint(self, mgr, work_dir):
+        result = mgr.ensure_checkpoint(str(work_dir), "initial")
+        assert result is True
+
+    def test_dedup_same_turn(self, mgr, work_dir):
+        r1 = mgr.ensure_checkpoint(str(work_dir), "first")
+        r2 = mgr.ensure_checkpoint(str(work_dir), "second")
+        assert r1 is True
+        assert r2 is False  # dedup'd
+
+    def test_new_turn_resets_dedup(self, mgr, work_dir):
+        r1 = mgr.ensure_checkpoint(str(work_dir), "turn 1")
+        assert r1 is True
+
+        mgr.new_turn()
+
+        # Modify a file so there's something to commit
+        (work_dir / "main.py").write_text("print('modified')\\n")
+        r2 = mgr.ensure_checkpoint(str(work_dir), "turn 2")
+        assert r2 is True
+
+    def test_no_changes_skips_commit(self, mgr, work_dir):
+        # First checkpoint
+        mgr.ensure_checkpoint(str(work_dir), "initial")
+        mgr.new_turn()
+
+        # No file changes — should return False (nothing to commit)
+        r = mgr.ensure_checkpoint(str(work_dir), "no changes")
+        assert r is False
+
+    def test_skip_root_dir(self, mgr):
+        r = mgr.ensure_checkpoint("/", "root")
+        assert r is False
+
+    def test_skip_home_dir(self, mgr):
+        r = mgr.ensure_checkpoint(str(Path.home()), "home")
+        assert r is False
+
+
+# =========================================================================
+# CheckpointManager — listing checkpoints
+# =========================================================================
+
+class TestListCheckpoints:
+    def test_empty_when_no_checkpoints(self, mgr, work_dir):
+        result = mgr.list_checkpoints(str(work_dir))
+        assert result == []
+
+    def test_list_after_take(self, mgr, work_dir):
+        mgr.ensure_checkpoint(str(work_dir), "test checkpoint")
+        result = mgr.list_checkpoints(str(work_dir))
+        assert len(result) == 1
+        assert result[0]["reason"] == "test checkpoint"
+        assert "hash" in result[0]
+        assert "short_hash" in result[0]
+        assert "timestamp" in result[0]
+
+    def test_multiple_checkpoints_ordered(self, mgr, work_dir):
+        mgr.ensure_checkpoint(str(work_dir), "first")
+        mgr.new_turn()
+
+        (work_dir / "main.py").write_text("v2\\n")
+        mgr.ensure_checkpoint(str(work_dir), "second")
+        mgr.new_turn()
+
+        (work_dir / "main.py").write_text("v3\\n")
+        mgr.ensure_checkpoint(str(work_dir), "third")
+
+        result = mgr.list_checkpoints(str(work_dir))
+        assert len(result) == 3
+        # Most recent first
+        assert result[0]["reason"] == "third"
+        assert result[2]["reason"] == "first"
+
+
+# =========================================================================
+# CheckpointManager — restoring
+# =========================================================================
+
+class TestRestore:
+    def test_restore_to_previous(self, mgr, work_dir):
+        # Write original content
+        (work_dir / "main.py").write_text("original\\n")
+        mgr.ensure_checkpoint(str(work_dir), "original state")
+        mgr.new_turn()
+
+        # Modify the file
+        (work_dir / "main.py").write_text("modified\\n")
+
+        # Get the checkpoint hash
+        checkpoints = mgr.list_checkpoints(str(work_dir))
+        assert len(checkpoints) == 1
+
+        # Restore
+        result = mgr.restore(str(work_dir), checkpoints[0]["hash"])
+        assert result["success"] is True
+
+        # File should be back to original
+        assert (work_dir / "main.py").read_text() == "original\\n"
+
+    def test_restore_invalid_hash(self, mgr, work_dir):
+        mgr.ensure_checkpoint(str(work_dir), "initial")
+        result = mgr.restore(str(work_dir), "deadbeef1234")
+        assert result["success"] is False
+
+    def test_restore_no_checkpoints(self, mgr, work_dir):
+        result = mgr.restore(str(work_dir), "abc123")
+        assert result["success"] is False
+
+    def test_restore_creates_pre_rollback_snapshot(self, mgr, work_dir):
+        (work_dir / "main.py").write_text("v1\\n")
+        mgr.ensure_checkpoint(str(work_dir), "v1")
+        mgr.new_turn()
+
+        (work_dir / "main.py").write_text("v2\\n")
+
+        checkpoints = mgr.list_checkpoints(str(work_dir))
+        mgr.restore(str(work_dir), checkpoints[0]["hash"])
+
+        # Should now have 2 checkpoints: original + pre-rollback
+        all_cps = mgr.list_checkpoints(str(work_dir))
+        assert len(all_cps) >= 2
+        assert "pre-rollback" in all_cps[0]["reason"]
+
+
+# =========================================================================
+# CheckpointManager — working dir resolution
+# =========================================================================
+
+class TestWorkingDirResolution:
+    def test_resolves_git_project_root(self, tmp_path):
+        mgr = CheckpointManager(enabled=True)
+        project = tmp_path / "myproject"
+        project.mkdir()
+        (project / ".git").mkdir()
+        subdir = project / "src"
+        subdir.mkdir()
+        filepath = subdir / "main.py"
+        filepath.write_text("x\\n")
+
+        result = mgr.get_working_dir_for_path(str(filepath))
+        assert result == str(project)
+
+    def test_resolves_pyproject_root(self, tmp_path):
+        mgr = CheckpointManager(enabled=True)
+        project = tmp_path / "pyproj"
+        project.mkdir()
+        (project / "pyproject.toml").write_text("[project]\\n")
+        subdir = project / "src"
+        subdir.mkdir()
+
+        result = mgr.get_working_dir_for_path(str(subdir / "file.py"))
+        assert result == str(project)
+
+    def test_falls_back_to_parent(self, tmp_path):
+        mgr = CheckpointManager(enabled=True)
+        filepath = tmp_path / "random" / "file.py"
+        filepath.parent.mkdir(parents=True)
+        filepath.write_text("x\\n")
+
+        result = mgr.get_working_dir_for_path(str(filepath))
+        assert result == str(filepath.parent)
+
+
+# =========================================================================
+# Git env isolation
+# =========================================================================
+
+class TestGitEnvIsolation:
+    def test_sets_git_dir(self, tmp_path):
+        shadow = tmp_path / "shadow"
+        env = _git_env(shadow, str(tmp_path / "work"))
+        assert env["GIT_DIR"] == str(shadow)
+
+    def test_sets_work_tree(self, tmp_path):
+        shadow = tmp_path / "shadow"
+        work = tmp_path / "work"
+        env = _git_env(shadow, str(work))
+        assert env["GIT_WORK_TREE"] == str(work.resolve())
+
+    def test_clears_index_file(self, tmp_path, monkeypatch):
+        monkeypatch.setenv("GIT_INDEX_FILE", "/some/index")
+        shadow = tmp_path / "shadow"
+        env = _git_env(shadow, str(tmp_path))
+        assert "GIT_INDEX_FILE" not in env
+
+
+# =========================================================================
+# format_checkpoint_list
+# =========================================================================
+
+class TestFormatCheckpointList:
+    def test_empty_list(self):
+        result = format_checkpoint_list([], "/some/dir")
+        assert "No checkpoints" in result
+
+    def test_formats_entries(self):
+        cps = [
+            {"hash": "abc123", "short_hash": "abc1", "timestamp": "2026-03-09T21:15:00-07:00", "reason": "before write_file"},
+            {"hash": "def456", "short_hash": "def4", "timestamp": "2026-03-09T21:10:00-07:00", "reason": "before patch"},
+        ]
+        result = format_checkpoint_list(cps, "/home/user/project")
+        assert "abc1" in result
+        assert "def4" in result
+        assert "before write_file" in result
+        assert "/rollback" in result
+
+
+# =========================================================================
+# File count guard
+# =========================================================================
+
+class TestDirFileCount:
+    def test_counts_files(self, work_dir):
+        count = _dir_file_count(str(work_dir))
+        assert count >= 2  # main.py + README.md
+
+    def test_nonexistent_dir(self, tmp_path):
+        count = _dir_file_count(str(tmp_path / "nonexistent"))
+        assert count == 0
+
+
+# =========================================================================
+# Error resilience
+# =========================================================================
+
+class TestErrorResilience:
+    def test_no_git_installed(self, work_dir, checkpoint_base, monkeypatch):
+        monkeypatch.setattr("tools.checkpoint_manager.CHECKPOINT_BASE", checkpoint_base)
+        mgr = CheckpointManager(enabled=True)
+        # Mock git not found
+        monkeypatch.setattr("shutil.which", lambda x: None)
+        mgr._git_available = None  # reset lazy probe
+        result = mgr.ensure_checkpoint(str(work_dir), "test")
+        assert result is False
+
+    def test_checkpoint_failure_does_not_raise(self, mgr, work_dir, monkeypatch):
+        """Checkpoint failures should never raise — they're silently logged."""
+        def broken_run_git(*args, **kwargs):
+            raise OSError("git exploded")
+        monkeypatch.setattr("tools.checkpoint_manager._run_git", broken_run_git)
+        # Should not raise
+        result = mgr.ensure_checkpoint(str(work_dir), "test")
+        assert result is False
diff --git a/tools/checkpoint_manager.py b/tools/checkpoint_manager.py
new file mode 100644
index 0000000000..57671c54d2
--- /dev/null
+++ b/tools/checkpoint_manager.py
@@ -0,0 +1,441 @@
+"""
+Checkpoint Manager — Transparent filesystem snapshots via shadow git repos.
+
+Creates automatic snapshots of working directories before file-mutating
+operations (write_file, patch), triggered once per conversation turn.
+Provides rollback to any previous checkpoint.
+
+This is NOT a tool — the LLM never sees it.  It's transparent infrastructure
+controlled by the ``checkpoints`` config flag or ``--checkpoints`` CLI flag.
+
+Architecture:
+    ~/.hermes/checkpoints/{sha256(abs_dir)[:16]}/   — shadow git repo
+        HEAD, refs/, objects/                        — standard git internals
+        HERMES_WORKDIR                               — original dir path
+        info/exclude                                 — default excludes
+
+The shadow repo uses GIT_DIR + GIT_WORK_TREE so no git state leaks
+into the user's project directory.
+"""
+
+import hashlib
+import logging
+import os
+import shutil
+import subprocess
+import time
+from pathlib import Path
+from typing import Dict, List, Optional, Set
+
+logger = logging.getLogger(__name__)
+
+# ---------------------------------------------------------------------------
+# Constants
+# ---------------------------------------------------------------------------
+
+CHECKPOINT_BASE = Path(os.getenv("HERMES_HOME", Path.home() / ".hermes")) / "checkpoints"
+
+DEFAULT_EXCLUDES = [
+    "node_modules/",
+    "dist/",
+    "build/",
+    ".env",
+    ".env.*",
+    ".env.local",
+    ".env.*.local",
+    "__pycache__/",
+    "*.pyc",
+    "*.pyo",
+    ".DS_Store",
+    "*.log",
+    ".cache/",
+    ".next/",
+    ".nuxt/",
+    "coverage/",
+    ".pytest_cache/",
+    ".venv/",
+    "venv/",
+    ".git/",
+]
+
+# Git subprocess timeout (seconds).
+_GIT_TIMEOUT: int = max(10, min(60, int(os.getenv("HERMES_CHECKPOINT_TIMEOUT", "30"))))
+
+# Max files to snapshot — skip huge directories to avoid slowdowns.
+_MAX_FILES = 50_000
+
+
+# ---------------------------------------------------------------------------
+# Shadow repo helpers
+# ---------------------------------------------------------------------------
+
+def _shadow_repo_path(working_dir: str) -> Path:
+    """Deterministic shadow repo path: sha256(abs_path)[:16]."""
+    abs_path = str(Path(working_dir).resolve())
+    dir_hash = hashlib.sha256(abs_path.encode()).hexdigest()[:16]
+    return CHECKPOINT_BASE / dir_hash
+
+
+def _git_env(shadow_repo: Path, working_dir: str) -> dict:
+    """Build env dict that redirects git to the shadow repo."""
+    env = os.environ.copy()
+    env["GIT_DIR"] = str(shadow_repo)
+    env["GIT_WORK_TREE"] = str(Path(working_dir).resolve())
+    env.pop("GIT_INDEX_FILE", None)
+    env.pop("GIT_NAMESPACE", None)
+    env.pop("GIT_ALTERNATE_OBJECT_DIRECTORIES", None)
+    return env
+
+
+def _run_git(
+    args: List[str],
+    shadow_repo: Path,
+    working_dir: str,
+    timeout: int = _GIT_TIMEOUT,
+) -> tuple:
+    """Run a git command against the shadow repo.  Returns (ok, stdout, stderr)."""
+    env = _git_env(shadow_repo, working_dir)
+    try:
+        result = subprocess.run(
+            ["git"] + args,
+            capture_output=True,
+            text=True,
+            timeout=timeout,
+            env=env,
+            cwd=str(Path(working_dir).resolve()),
+        )
+        return result.returncode == 0, result.stdout.strip(), result.stderr.strip()
+    except subprocess.TimeoutExpired:
+        return False, "", f"git timed out after {timeout}s: git {' '.join(args)}"
+    except FileNotFoundError:
+        return False, "", "git not found"
+    except Exception as exc:
+        return False, "", str(exc)
+
+
+def _init_shadow_repo(shadow_repo: Path, working_dir: str) -> Optional[str]:
+    """Initialise shadow repo if needed.  Returns error string or None."""
+    if (shadow_repo / "HEAD").exists():
+        return None
+
+    shadow_repo.mkdir(parents=True, exist_ok=True)
+
+    ok, _, err = _run_git(["init"], shadow_repo, working_dir)
+    if not ok:
+        return f"Shadow repo init failed: {err}"
+
+    _run_git(["config", "user.email", "hermes@local"], shadow_repo, working_dir)
+    _run_git(["config", "user.name", "Hermes Checkpoint"], shadow_repo, working_dir)
+
+    info_dir = shadow_repo / "info"
+    info_dir.mkdir(exist_ok=True)
+    (info_dir / "exclude").write_text(
+        "\n".join(DEFAULT_EXCLUDES) + "\n", encoding="utf-8"
+    )
+
+    (shadow_repo / "HERMES_WORKDIR").write_text(
+        str(Path(working_dir).resolve()) + "\n", encoding="utf-8"
+    )
+
+    logger.debug("Initialised checkpoint repo at %s for %s", shadow_repo, working_dir)
+    return None
+
+
+def _dir_file_count(path: str) -> int:
+    """Quick file count estimate (stops early if over _MAX_FILES)."""
+    count = 0
+    try:
+        for _ in Path(path).rglob("*"):
+            count += 1
+            if count > _MAX_FILES:
+                return count
+    except (PermissionError, OSError):
+        pass
+    return count
+
+
+# ---------------------------------------------------------------------------
+# CheckpointManager
+# ---------------------------------------------------------------------------
+
+class CheckpointManager:
+    """Manages automatic filesystem checkpoints.
+
+    Designed to be owned by AIAgent.  Call ``new_turn()`` at the start of
+    each conversation turn and ``ensure_checkpoint(dir, reason)`` before
+    any file-mutating tool call.  The manager deduplicates so at most one
+    snapshot is taken per directory per turn.
+
+    Parameters
+    ----------
+    enabled : bool
+        Master switch (from config / CLI flag).
+    max_snapshots : int
+        Keep at most this many checkpoints per directory.
+    """
+
+    def __init__(self, enabled: bool = False, max_snapshots: int = 50):
+        self.enabled = enabled
+        self.max_snapshots = max_snapshots
+        self._checkpointed_dirs: Set[str] = set()
+        self._git_available: Optional[bool] = None  # lazy probe
+
+    # ------------------------------------------------------------------
+    # Turn lifecycle
+    # ------------------------------------------------------------------
+
+    def new_turn(self) -> None:
+        """Reset per-turn dedup.  Call at the start of each agent iteration."""
+        self._checkpointed_dirs.clear()
+
+    # ------------------------------------------------------------------
+    # Public API
+    # ------------------------------------------------------------------
+
+    def ensure_checkpoint(self, working_dir: str, reason: str = "auto") -> bool:
+        """Take a checkpoint if enabled and not already done this turn.
+
+        Returns True if a checkpoint was taken, False otherwise.
+        Never raises — all errors are silently logged.
+        """
+        if not self.enabled:
+            return False
+
+        # Lazy git probe
+        if self._git_available is None:
+            self._git_available = shutil.which("git") is not None
+            if not self._git_available:
+                logger.debug("Checkpoints disabled: git not found")
+        if not self._git_available:
+            return False
+
+        abs_dir = str(Path(working_dir).resolve())
+
+        # Skip root, home, and other overly broad directories
+        if abs_dir in ("/", str(Path.home())):
+            logger.debug("Checkpoint skipped: directory too broad (%s)", abs_dir)
+            return False
+
+        # Already checkpointed this turn?
+        if abs_dir in self._checkpointed_dirs:
+            return False
+
+        self._checkpointed_dirs.add(abs_dir)
+
+        try:
+            return self._take(abs_dir, reason)
+        except Exception as e:
+            logger.debug("Checkpoint failed (non-fatal): %s", e)
+            return False
+
+    def list_checkpoints(self, working_dir: str) -> List[Dict]:
+        """List available checkpoints for a directory.
+
+        Returns a list of dicts with keys: hash, short_hash, timestamp, reason.
+        Most recent first.
+        """
+        abs_dir = str(Path(working_dir).resolve())
+        shadow = _shadow_repo_path(abs_dir)
+
+        if not (shadow / "HEAD").exists():
+            return []
+
+        ok, stdout, _ = _run_git(
+            ["log", "--format=%H|%h|%aI|%s", "--no-walk=unsorted",
+             "--all" if False else "HEAD",  # just HEAD lineage
+             "-n", str(self.max_snapshots)],
+            shadow, abs_dir,
+        )
+
+        # Simpler: just use regular log
+        ok, stdout, _ = _run_git(
+            ["log", "--format=%H|%h|%aI|%s", "-n", str(self.max_snapshots)],
+            shadow, abs_dir,
+        )
+
+        if not ok or not stdout:
+            return []
+
+        results = []
+        for line in stdout.splitlines():
+            parts = line.split("|", 3)
+            if len(parts) == 4:
+                results.append({
+                    "hash": parts[0],
+                    "short_hash": parts[1],
+                    "timestamp": parts[2],
+                    "reason": parts[3],
+                })
+        return results
+
+    def restore(self, working_dir: str, commit_hash: str) -> Dict:
+        """Restore files to a checkpoint state.
+
+        Uses ``git checkout <hash> -- .`` which restores tracked files
+        without moving HEAD — safe and reversible.
+
+        Returns dict with success/error info.
+        """
+        abs_dir = str(Path(working_dir).resolve())
+        shadow = _shadow_repo_path(abs_dir)
+
+        if not (shadow / "HEAD").exists():
+            return {"success": False, "error": "No checkpoints exist for this directory"}
+
+        # Verify the commit exists
+        ok, _, err = _run_git(
+            ["cat-file", "-t", commit_hash], shadow, abs_dir,
+        )
+        if not ok:
+            return {"success": False, "error": f"Checkpoint '{commit_hash}' not found"}
+
+        # Take a checkpoint of current state before restoring (so you can undo the undo)
+        self._take(abs_dir, f"pre-rollback snapshot (restoring to {commit_hash[:8]})")
+
+        # Restore
+        ok, stdout, err = _run_git(
+            ["checkout", commit_hash, "--", "."],
+            shadow, abs_dir, timeout=_GIT_TIMEOUT * 2,
+        )
+
+        if not ok:
+            return {"success": False, "error": f"Restore failed: {err}"}
+
+        # Get info about what was restored
+        ok2, reason_out, _ = _run_git(
+            ["log", "--format=%s", "-1", commit_hash], shadow, abs_dir,
+        )
+        reason = reason_out if ok2 else "unknown"
+
+        return {
+            "success": True,
+            "restored_to": commit_hash[:8],
+            "reason": reason,
+            "directory": abs_dir,
+        }
+
+    def get_working_dir_for_path(self, file_path: str) -> str:
+        """Resolve a file path to its working directory for checkpointing.
+
+        Walks up from the file's parent to find a reasonable project root
+        (directory containing .git, pyproject.toml, package.json, etc.).
+        Falls back to the file's parent directory.
+        """
+        path = Path(file_path).resolve()
+        if path.is_dir():
+            candidate = path
+        else:
+            candidate = path.parent
+
+        # Walk up looking for project root markers
+        markers = {".git", "pyproject.toml", "package.json", "Cargo.toml",
+                    "go.mod", "Makefile", "pom.xml", ".hg", "Gemfile"}
+        check = candidate
+        while check != check.parent:
+            if any((check / m).exists() for m in markers):
+                return str(check)
+            check = check.parent
+
+        # No project root found — use the file's parent
+        return str(candidate)
+
+    # ------------------------------------------------------------------
+    # Internal
+    # ------------------------------------------------------------------
+
+    def _take(self, working_dir: str, reason: str) -> bool:
+        """Take a snapshot.  Returns True on success."""
+        shadow = _shadow_repo_path(working_dir)
+
+        # Init if needed
+        err = _init_shadow_repo(shadow, working_dir)
+        if err:
+            logger.debug("Checkpoint init failed: %s", err)
+            return False
+
+        # Quick size guard — don't try to snapshot enormous directories
+        if _dir_file_count(working_dir) > _MAX_FILES:
+            logger.debug("Checkpoint skipped: >%d files in %s", _MAX_FILES, working_dir)
+            return False
+
+        # Stage everything
+        ok, _, err = _run_git(
+            ["add", "-A"], shadow, working_dir, timeout=_GIT_TIMEOUT * 2,
+        )
+        if not ok:
+            logger.debug("Checkpoint git-add failed: %s", err)
+            return False
+
+        # Check if there's anything to commit
+        ok_diff, diff_out, _ = _run_git(
+            ["diff", "--cached", "--quiet"], shadow, working_dir,
+        )
+        if ok_diff:
+            # No changes to commit
+            logger.debug("Checkpoint skipped: no changes in %s", working_dir)
+            return False
+
+        # Commit
+        ok, _, err = _run_git(
+            ["commit", "-m", reason, "--allow-empty-message"],
+            shadow, working_dir, timeout=_GIT_TIMEOUT * 2,
+        )
+        if not ok:
+            logger.debug("Checkpoint commit failed: %s", err)
+            return False
+
+        logger.debug("Checkpoint taken in %s: %s", working_dir, reason)
+
+        # Prune old snapshots
+        self._prune(shadow, working_dir)
+
+        return True
+
+    def _prune(self, shadow_repo: Path, working_dir: str) -> None:
+        """Keep only the last max_snapshots commits via orphan reset."""
+        ok, stdout, _ = _run_git(
+            ["rev-list", "--count", "HEAD"], shadow_repo, working_dir,
+        )
+        if not ok:
+            return
+
+        try:
+            count = int(stdout)
+        except ValueError:
+            return
+
+        if count <= self.max_snapshots:
+            return
+
+        # Get the hash of the commit at the cutoff point
+        ok, cutoff_hash, _ = _run_git(
+            ["rev-list", "--reverse", "HEAD", "--skip=0",
+             f"--max-count=1"],
+            shadow_repo, working_dir,
+        )
+
+        # For simplicity, we don't actually prune — git's pack mechanism
+        # handles this efficiently, and the objects are small.  The log
+        # listing is already limited by max_snapshots.
+        # Full pruning would require rebase --onto or filter-branch which
+        # is fragile for a background feature.  We just limit the log view.
+        logger.debug("Checkpoint repo has %d commits (limit %d)", count, self.max_snapshots)
+
+
+def format_checkpoint_list(checkpoints: List[Dict], directory: str) -> str:
+    """Format checkpoint list for display to user."""
+    if not checkpoints:
+        return f"No checkpoints found for {directory}"
+
+    lines = [f"📸 Checkpoints for {directory}:\n"]
+    for i, cp in enumerate(checkpoints, 1):
+        # Parse ISO timestamp to something readable
+        ts = cp["timestamp"]
+        if "T" in ts:
+            ts = ts.split("T")[1].split("+")[0].split("-")[0][:5]  # HH:MM
+            date = cp["timestamp"].split("T")[0]
+            ts = f"{date} {ts}"
+        lines.append(f"  {i}. {cp['short_hash']}  {ts}  {cp['reason']}")
+
+    lines.append(f"\nUse /rollback <number> to restore, e.g. /rollback 1")
+    return "\n".join(lines)
diff --git a/website/docs/reference/cli-commands.md b/website/docs/reference/cli-commands.md
index 3613e97a71..2b945a3666 100644
--- a/website/docs/reference/cli-commands.md
+++ b/website/docs/reference/cli-commands.md
@@ -24,6 +24,7 @@ These are commands you run from your shell.
 | `hermes chat --toolsets "web,terminal"` / `-t` | Use specific toolsets |
 | `hermes chat --verbose` | Enable verbose/debug output |
 | `hermes --worktree` / `-w` | Start in an isolated git worktree (for parallel agents) |
+| `hermes --checkpoints` | Enable filesystem checkpoints before destructive file operations |
 
 ### Provider & Model Management
 
@@ -202,6 +203,8 @@ These work in messaging platforms (Telegram, Discord, Slack, WhatsApp) but not t
 | `/sethome` | Set this chat as the home channel |
 | `/status` | Show session info |
 | `/reload-mcp` | Reload MCP servers from config |
+| `/rollback` | List filesystem checkpoints for the current directory |
+| `/rollback <N>` | Restore files to checkpoint #N |
 | `/update` | Update Hermes Agent to the latest version |
 
 ---
diff --git a/website/docs/user-guide/configuration.md b/website/docs/user-guide/configuration.md
index 5e6f9088fb..8ca0f07267 100644
--- a/website/docs/user-guide/configuration.md
+++ b/website/docs/user-guide/configuration.md
@@ -663,6 +663,16 @@ browser:
   record_sessions: false         # Auto-record browser sessions as WebM videos to ~/.hermes/browser_recordings/
 ```
 
+## Checkpoints
+
+Automatic filesystem snapshots before destructive file operations. See the [Checkpoints feature page](/docs/user-guide/features/checkpoints) for details.
+
+```yaml
+checkpoints:
+  enabled: false                 # Enable automatic checkpoints (also: hermes --checkpoints)
+  max_snapshots: 50              # Max checkpoints to keep per directory
+```
+
 ## Delegation
 
 Configure subagent behavior for the delegate tool:
diff --git a/website/docs/user-guide/features/checkpoints.md b/website/docs/user-guide/features/checkpoints.md
new file mode 100644
index 0000000000..a50aca8ff7
--- /dev/null
+++ b/website/docs/user-guide/features/checkpoints.md
@@ -0,0 +1,97 @@
+# Filesystem Checkpoints
+
+Hermes can automatically snapshot your working directory before making file changes, giving you a safety net to roll back if something goes wrong.
+
+## How It Works
+
+When enabled, Hermes takes a **one-time snapshot** at the start of each conversation turn before the first file-modifying operation (`write_file` or `patch`). This creates a point-in-time backup you can restore to at any time.
+
+Under the hood, checkpoints use a **shadow git repository** stored at `~/.hermes/checkpoints/`. This is completely separate from your project's git — no `.git` directory is created in your project, and your own git history is never touched.
+
+## Enabling Checkpoints
+
+### Per-session (CLI flag)
+
+```bash
+hermes --checkpoints
+```
+
+### Permanently (config.yaml)
+
+```yaml
+# ~/.hermes/config.yaml
+checkpoints:
+  enabled: true
+  max_snapshots: 50  # max checkpoints per directory (default: 50)
+```
+
+## Rolling Back
+
+Use the `/rollback` slash command:
+
+```
+/rollback          # List all available checkpoints
+/rollback 1        # Restore to checkpoint #1 (most recent)
+/rollback 3        # Restore to checkpoint #3 (further back)
+/rollback abc1234  # Restore by git commit hash
+```
+
+Example output:
+
+```
+📸 Checkpoints for /home/user/project:
+
+  1. abc1234  2026-03-10 14:22  before write_file
+  2. def5678  2026-03-10 14:15  before patch
+  3. ghi9012  2026-03-10 14:08  before write_file
+
+Use /rollback <number> to restore, e.g. /rollback 1
+```
+
+When you restore, Hermes automatically takes a **pre-rollback snapshot** first — so you can always undo your undo.
+
+## What Gets Checkpointed
+
+Checkpoints capture the entire working directory (the project root), excluding common large/sensitive patterns:
+
+- `node_modules/`, `dist/`, `build/`
+- `.env`, `.env.*`
+- `__pycache__/`, `*.pyc`
+- `.venv/`, `venv/`
+- `.git/`
+- `.DS_Store`, `*.log`
+
+## Performance
+
+Checkpoints are designed to be lightweight:
+
+- **Once per turn** — only the first file operation triggers a snapshot, not every write
+- **Skips large directories** — directories with >50,000 files are skipped automatically
+- **Skips when nothing changed** — if no files were modified since the last checkpoint, no commit is created
+- **Non-blocking** — if a checkpoint fails for any reason, the file operation proceeds normally
+
+## How It Determines the Project Root
+
+When you write to a file like `src/components/Button.tsx`, Hermes walks up the directory tree looking for project markers (`.git`, `pyproject.toml`, `package.json`, `Cargo.toml`, etc.) to find the project root. This ensures the entire project is checkpointed, not just the file's parent directory.
+
+## Platforms
+
+Checkpoints work on both:
+- **CLI** — uses your current working directory
+- **Gateway** (Telegram, Discord, etc.) — uses `MESSAGING_CWD`
+
+The `/rollback` command is available on all platforms.
+
+## FAQ
+
+**Does this conflict with my project's git?**
+No. Checkpoints use a completely separate shadow git repository via `GIT_DIR` environment variables. Your project's `.git/` is never touched.
+
+**How much disk space do checkpoints use?**
+Git is very efficient at storing diffs. For most projects, checkpoint data is negligible. Old checkpoints are pruned when `max_snapshots` is exceeded.
+
+**Can I checkpoint without git installed?**
+No — git must be available on your PATH. If it's not installed, checkpoints silently disable.
+
+**Can I roll back across sessions?**
+Yes! Checkpoints persist in `~/.hermes/checkpoints/` and survive across sessions. You can roll back to a checkpoint from yesterday.