diff --git a/gateway/run.py b/gateway/run.py
index 0b778e2f67..4d22a4d69d 100644
--- a/gateway/run.py
+++ b/gateway/run.py
@@ -1756,6 +1756,9 @@ class GatewayRunner:
         await asyncio.sleep(60)  # initial delay — let the gateway fully start
         _flush_failures: dict[str, int] = {}  # session_id -> consecutive failure count
         _MAX_FLUSH_RETRIES = 3
+        # Daily artifact cleanup: 288 cycles × 5-min interval ≈ 24h
+        _ARTIFACT_CLEANUP_EVERY = max(1, (24 * 3600) // interval)
+        _artifact_tick = 0
         while self._running:
             try:
                 self.session_store._ensure_loaded()
@@ -1856,6 +1859,30 @@ class GatewayRunner:
                         )
             except Exception as e:
                 logger.debug("Session expiry watcher error: %s", e)
+
+            # --- Daily disk artifact cleanup ---
+            # Run once per day (every 288 cycles at 5-min interval = 24h).
+            # Cleans up stale session transcript files and checkpoint directories.
+            _artifact_tick += 1
+            if _artifact_tick >= _ARTIFACT_CLEANUP_EVERY:
+                _artifact_tick = 0
+                try:
+                    from tools.session_cleanup import prune_all_artifacts
+                    _hermes_home = get_hermes_home()
+                    _results = await asyncio.get_event_loop().run_in_executor(
+                        None,
+                        lambda: prune_all_artifacts(_hermes_home, self._session_db),
+                    )
+                    _total_freed = sum(v[1] for v in _results.values())
+                    _total_count = sum(v[0] for v in _results.values())
+                    if _total_count:
+                        logger.info(
+                            "Artifact cleanup: removed %d items, freed %d KB",
+                            _total_count, _total_freed // 1024,
+                        )
+                except Exception as e:
+                    logger.debug("Artifact cleanup error: %s", e)
+
             # Sleep in small increments so we can stop quickly
             for _ in range(interval):
                 if not self._running:
diff --git a/hermes_cli/main.py b/hermes_cli/main.py
index 1e04008844..fd86e2437d 100644
--- a/hermes_cli/main.py
+++ b/hermes_cli/main.py
@@ -5397,6 +5397,12 @@ For more help on a command:
     sessions_prune.add_argument("--older-than", type=int, default=90, help="Delete sessions older than N days (default: 90)")
     sessions_prune.add_argument("--source", help="Only prune sessions from this source")
     sessions_prune.add_argument("--yes", "-y", action="store_true", help="Skip confirmation")
+    sessions_prune.add_argument("--include-files", action="store_true",
+                                help="Also delete session transcript files and stale checkpoints from disk")
+    sessions_prune.add_argument("--files-only", action="store_true",
+                                help="Only clean disk files (session transcripts, request dumps, checkpoints) — skip DB pruning")
+    sessions_prune.add_argument("--dry-run", action="store_true",
+                                help="Show what would be deleted without actually deleting")
 
     sessions_subparsers.add_parser("stats", help="Show session store statistics")
 
@@ -5503,12 +5509,50 @@ For more help on a command:
         elif action == "prune":
             days = args.older_than
             source_msg = f" from '{args.source}'" if args.source else ""
-            if not args.yes:
-                if not _confirm_prompt(f"Delete all ended sessions older than {days} days{source_msg}? [y/N] "):
+            files_only = getattr(args, "files_only", False)
+            include_files = getattr(args, "include_files", False) or files_only
+            dry_run = getattr(args, "dry_run", False)
+
+            if dry_run:
+                print("Dry run — showing what would be deleted:\n")
+            elif not args.yes:
+                if files_only:
+                    prompt_msg = f"Clean up disk files (session transcripts, request dumps, checkpoints) older than {days} days? [y/N] "
+                elif include_files:
+                    prompt_msg = f"Delete all ended sessions older than {days} days{source_msg} AND clean up disk files? [y/N] "
+                else:
+                    prompt_msg = f"Delete all ended sessions older than {days} days{source_msg}? [y/N] "
+                if not _confirm_prompt(prompt_msg):
                     print("Cancelled.")
                     return
-            count = db.prune_sessions(older_than_days=days, source=args.source)
-            print(f"Pruned {count} session(s).")
+
+            # DB pruning (skip if --files-only)
+            if not files_only:
+                if dry_run:
+                    print(f"DB: Would prune ended sessions older than {days} days{source_msg}.")
+                    print("  (Use without --dry-run to see exact count)")
+                else:
+                    count = db.prune_sessions(older_than_days=days, source=args.source)
+                    print(f"Pruned {count} session(s) from database.")
+
+            # Disk file cleanup
+            if include_files:
+                try:
+                    from tools.session_cleanup import prune_all_artifacts, format_prune_summary
+                    hermes_home = get_hermes_home()
+                    results = prune_all_artifacts(
+                        hermes_home, db,
+                        session_retention_days=days,
+                        checkpoint_retention_days=min(days, 14),
+                        dry_run=dry_run,
+                    )
+                    summary = format_prune_summary(results)
+                    if dry_run:
+                        print(f"\nDisk files that would be cleaned:\n{summary}")
+                    else:
+                        print(f"\nDisk cleanup:\n{summary}")
+                except Exception as e:
+                    print(f"Disk cleanup failed: {e}")
 
         elif action == "rename":
             resolved_session_id = db.resolve_session_id(args.session_id)
@@ -5567,6 +5611,30 @@ For more help on a command:
                 size_mb = os.path.getsize(db_path) / (1024 * 1024)
                 print(f"Database size: {size_mb:.1f} MB")
 
+            # Disk artifact stats
+            hermes_home = get_hermes_home()
+            sessions_dir = hermes_home / "sessions"
+            checkpoints_dir = hermes_home / "checkpoints"
+            if sessions_dir.exists():
+                session_files = list(sessions_dir.glob("session_*.json"))
+                request_dumps = list(sessions_dir.glob("request_dump_*.json"))
+                jsonl_files = list(sessions_dir.glob("*.jsonl"))
+                session_bytes = sum(f.stat().st_size for f in session_files if f.is_file())
+                dump_bytes = sum(f.stat().st_size for f in request_dumps if f.is_file())
+                jsonl_bytes = sum(f.stat().st_size for f in jsonl_files if f.is_file())
+                print(f"\nDisk artifacts:")
+                if session_files:
+                    print(f"  Session transcripts: {len(session_files)} files ({session_bytes / (1024*1024):.1f} MB)")
+                if request_dumps:
+                    print(f"  Request dumps:       {len(request_dumps)} files ({dump_bytes / (1024*1024):.1f} MB)")
+                if jsonl_files:
+                    print(f"  Gateway transcripts: {len(jsonl_files)} files ({jsonl_bytes / (1024*1024):.1f} MB)")
+            if checkpoints_dir.exists():
+                cp_dirs = [d for d in checkpoints_dir.iterdir() if d.is_dir()]
+                if cp_dirs:
+                    print(f"  Checkpoints:         {len(cp_dirs)} directories")
+            print(f"\n  Tip: Use 'hermes sessions prune --include-files' to clean up old disk artifacts.")
+
         else:
             sessions_parser.print_help()
 
diff --git a/hermes_cli/tips.py b/hermes_cli/tips.py
index bb9f9e60cd..7b314b3db6 100644
--- a/hermes_cli/tips.py
+++ b/hermes_cli/tips.py
@@ -84,7 +84,8 @@ TIPS = [
     "hermes config check scans for missing or stale configuration options.",
     "hermes sessions browse opens an interactive session picker with search.",
     "hermes sessions stats shows session counts by platform and database size.",
-    "hermes sessions prune --older-than 30 cleans up old sessions.",
+    "hermes sessions prune --older-than 30 cleans up old sessions from the database.",
+    "hermes sessions prune --include-files cleans up both DB records AND disk artifacts (transcripts, checkpoints).",
     "hermes skills search react --source skills-sh searches the skills.sh public directory.",
     "hermes skills check scans installed hub skills for upstream updates.",
     "hermes skills tap add myorg/skills-repo adds a custom GitHub skill source.",
diff --git a/tests/tools/test_session_cleanup.py b/tests/tools/test_session_cleanup.py
new file mode 100644
index 0000000000..3f481bd875
--- /dev/null
+++ b/tests/tools/test_session_cleanup.py
@@ -0,0 +1,304 @@
+"""Tests for tools/session_cleanup.py — session artifact disk cleanup."""
+
+import os
+import json
+import time
+import shutil
+import tempfile
+from pathlib import Path
+from unittest.mock import MagicMock
+
+import pytest
+
+# Import the module under test
+import sys
+sys.path.insert(0, os.path.join(os.path.dirname(__file__), "..", ".."))
+from tools.session_cleanup import (
+    _extract_session_id_from_filename,
+    _get_active_session_ids,
+    _human_size,
+    format_prune_summary,
+    prune_all_artifacts,
+    prune_checkpoints,
+    prune_session_files,
+    SESSION_FILE_RETENTION_DAYS,
+    CHECKPOINT_RETENTION_DAYS,
+)
+
+
+# ─── Filename extraction ────────────────────────────────────────────────────
+
+
+class TestExtractSessionId:
+    def test_session_json(self):
+        assert _extract_session_id_from_filename("session_20260412_171123_466c.json") == "20260412_171123_466c"
+
+    def test_session_uuid(self):
+        assert _extract_session_id_from_filename("session_13bac027-2f82-4267-a0c6-1c37a032945a.json") == \
+               "13bac027-2f82-4267-a0c6-1c37a032945a"
+
+    def test_request_dump(self):
+        result = _extract_session_id_from_filename(
+            "request_dump_20260412_171123_466c_20260412_171125_789abc.json"
+        )
+        assert result == "20260412_171123_466c"
+
+    def test_jsonl_transcript(self):
+        assert _extract_session_id_from_filename("20260412_012806_2013cd04.jsonl") == "20260412_012806_2013cd04"
+
+    def test_unknown_format(self):
+        assert _extract_session_id_from_filename("random_file.txt") is None
+
+    def test_sessions_json_state_file(self):
+        """sessions.json should return None — it's not a session artifact."""
+        assert _extract_session_id_from_filename("sessions.json") is None
+
+
+# ─── Active session detection ────────────────────────────────────────────────
+
+
+class TestGetActiveSessionIds:
+    def test_returns_active_ids(self):
+        db = MagicMock()
+        db.list_sessions_rich.return_value = [
+            {"id": "active1", "ended_at": None},
+            {"id": "ended1", "ended_at": 1234567890.0},
+            {"id": "active2", "ended_at": None},
+        ]
+        result = _get_active_session_ids(db)
+        assert result == {"active1", "active2"}
+
+    def test_returns_empty_on_error(self):
+        db = MagicMock()
+        db.list_sessions_rich.side_effect = Exception("DB error")
+        result = _get_active_session_ids(db)
+        assert result == set()
+
+
+# ─── Session file pruning ────────────────────────────────────────────────────
+
+
+class TestPruneSessionFiles:
+    @pytest.fixture
+    def sessions_dir(self, tmp_path):
+        d = tmp_path / "sessions"
+        d.mkdir()
+        return d
+
+    @pytest.fixture
+    def mock_db(self):
+        db = MagicMock()
+        db.list_sessions_rich.return_value = [
+            {"id": "active_session_1", "ended_at": None},
+        ]
+        return db
+
+    def _create_old_file(self, directory, filename, age_days=60, content="{}"):
+        """Create a file with a modification time in the past."""
+        f = directory / filename
+        f.write_text(content)
+        old_time = time.time() - (age_days * 86400)
+        os.utime(f, (old_time, old_time))
+        return f
+
+    def test_deletes_old_session_files(self, sessions_dir, mock_db):
+        self._create_old_file(sessions_dir, "session_old_ended_1.json", age_days=60)
+        self._create_old_file(sessions_dir, "session_old_ended_2.json", age_days=45)
+
+        files_del, bytes_freed = prune_session_files(
+            sessions_dir, mock_db, retention_days=30
+        )
+        assert files_del == 2
+        assert bytes_freed > 0
+        assert not (sessions_dir / "session_old_ended_1.json").exists()
+        assert not (sessions_dir / "session_old_ended_2.json").exists()
+
+    def test_preserves_recent_files(self, sessions_dir, mock_db):
+        # Recent file (5 days old) — should NOT be deleted
+        recent = sessions_dir / "session_recent_1.json"
+        recent.write_text("{}")
+        old_time = time.time() - (5 * 86400)
+        os.utime(recent, (old_time, old_time))
+
+        files_del, _ = prune_session_files(sessions_dir, mock_db, retention_days=30)
+        assert files_del == 0
+        assert recent.exists()
+
+    def test_preserves_active_session_files(self, sessions_dir, mock_db):
+        """Files belonging to active sessions should never be deleted."""
+        self._create_old_file(
+            sessions_dir, "session_active_session_1.json", age_days=60
+        )
+        files_del, _ = prune_session_files(sessions_dir, mock_db, retention_days=30)
+        assert files_del == 0
+        assert (sessions_dir / "session_active_session_1.json").exists()
+
+    def test_preserves_sessions_json_state_file(self, sessions_dir, mock_db):
+        """sessions.json must never be deleted."""
+        self._create_old_file(sessions_dir, "sessions.json", age_days=365)
+        files_del, _ = prune_session_files(sessions_dir, mock_db, retention_days=1)
+        assert files_del == 0
+        assert (sessions_dir / "sessions.json").exists()
+
+    def test_deletes_old_request_dumps(self, sessions_dir, mock_db):
+        self._create_old_file(
+            sessions_dir,
+            "request_dump_old_ended_1_20260412_171125_789abc.json",
+            age_days=60,
+        )
+        files_del, _ = prune_session_files(sessions_dir, mock_db, retention_days=30)
+        assert files_del == 1
+
+    def test_deletes_old_jsonl_transcripts(self, sessions_dir, mock_db):
+        self._create_old_file(sessions_dir, "20260312_012806_2013cd04.jsonl", age_days=60)
+        files_del, _ = prune_session_files(sessions_dir, mock_db, retention_days=30)
+        assert files_del == 1
+
+    def test_dry_run_does_not_delete(self, sessions_dir, mock_db):
+        f = self._create_old_file(sessions_dir, "session_dry_run_test.json", age_days=60)
+        files_del, _ = prune_session_files(
+            sessions_dir, mock_db, retention_days=30, dry_run=True
+        )
+        # Dry run returns 0 because nothing was actually deleted
+        assert files_del == 0
+        assert f.exists()
+
+    def test_nonexistent_directory(self, tmp_path, mock_db):
+        fake_dir = tmp_path / "nonexistent"
+        files_del, bytes_freed = prune_session_files(fake_dir, mock_db)
+        assert files_del == 0
+        assert bytes_freed == 0
+
+
+# ─── Checkpoint pruning ──────────────────────────────────────────────────────
+
+
+class TestPruneCheckpoints:
+    @pytest.fixture
+    def checkpoints_dir(self, tmp_path):
+        d = tmp_path / "checkpoints"
+        d.mkdir()
+        return d
+
+    def _create_old_checkpoint(self, directory, name, age_days=30, size_kb=10):
+        """Create a checkpoint directory with some content."""
+        cp = directory / name
+        cp.mkdir()
+        # Create some files to simulate a git repo
+        (cp / "HEAD").write_text("ref: refs/heads/master\n")
+        (cp / "config").write_text("[core]\n\trepositoryformatversion = 0\n")
+        (cp / "HERMES_WORKDIR").write_text("/tmp/test\n")
+        # Create filler data
+        (cp / "objects").mkdir()
+        (cp / "objects" / "data").write_bytes(b"x" * (size_kb * 1024))
+
+        old_time = time.time() - (age_days * 86400)
+        os.utime(cp, (old_time, old_time))
+        return cp
+
+    def test_deletes_old_checkpoints(self, checkpoints_dir):
+        self._create_old_checkpoint(checkpoints_dir, "abc123", age_days=30)
+        self._create_old_checkpoint(checkpoints_dir, "def456", age_days=20)
+
+        dirs_del, bytes_freed = prune_checkpoints(
+            checkpoints_dir, retention_days=14
+        )
+        assert dirs_del == 2
+        assert bytes_freed > 0
+        assert not (checkpoints_dir / "abc123").exists()
+        assert not (checkpoints_dir / "def456").exists()
+
+    def test_preserves_recent_checkpoints(self, checkpoints_dir):
+        self._create_old_checkpoint(checkpoints_dir, "recent1", age_days=5)
+
+        dirs_del, _ = prune_checkpoints(checkpoints_dir, retention_days=14)
+        assert dirs_del == 0
+        assert (checkpoints_dir / "recent1").exists()
+
+    def test_dry_run_does_not_delete(self, checkpoints_dir):
+        cp = self._create_old_checkpoint(checkpoints_dir, "dryrun1", age_days=30)
+        dirs_del, _ = prune_checkpoints(
+            checkpoints_dir, retention_days=14, dry_run=True
+        )
+        assert dirs_del == 0
+        assert cp.exists()
+
+    def test_nonexistent_directory(self, tmp_path):
+        fake_dir = tmp_path / "nonexistent"
+        dirs_del, bytes_freed = prune_checkpoints(fake_dir)
+        assert dirs_del == 0
+        assert bytes_freed == 0
+
+
+# ─── prune_all_artifacts integration ─────────────────────────────────────────
+
+
+class TestPruneAllArtifacts:
+    @pytest.fixture
+    def hermes_home(self, tmp_path):
+        h = tmp_path / "hermes"
+        (h / "sessions").mkdir(parents=True)
+        (h / "checkpoints").mkdir(parents=True)
+        return h
+
+    @pytest.fixture
+    def mock_db(self):
+        db = MagicMock()
+        db.list_sessions_rich.return_value = []
+        return db
+
+    def test_returns_results_for_all_types(self, hermes_home, mock_db):
+        results = prune_all_artifacts(hermes_home, mock_db)
+        assert "session_files" in results
+        assert "checkpoints" in results
+
+    def test_combined_cleanup(self, hermes_home, mock_db):
+        # Create old session file
+        sf = hermes_home / "sessions" / "session_old_test.json"
+        sf.write_text("{}")
+        old_time = time.time() - (60 * 86400)
+        os.utime(sf, (old_time, old_time))
+
+        # Create old checkpoint
+        cp = hermes_home / "checkpoints" / "oldcp"
+        cp.mkdir()
+        (cp / "HEAD").write_text("ref: refs/heads/master\n")
+        os.utime(cp, (old_time, old_time))
+
+        results = prune_all_artifacts(
+            hermes_home, mock_db,
+            session_retention_days=30,
+            checkpoint_retention_days=14,
+        )
+        assert results["session_files"][0] == 1
+        assert results["checkpoints"][0] == 1
+
+
+# ─── Formatting ──────────────────────────────────────────────────────────────
+
+
+class TestFormatPruneSummary:
+    def test_no_artifacts(self):
+        results = {"session_files": (0, 0), "checkpoints": (0, 0)}
+        assert format_prune_summary(results) == "No stale artifacts found."
+
+    def test_with_files(self):
+        results = {"session_files": (5, 1024 * 1024 * 100), "checkpoints": (3, 1024 * 1024 * 500)}
+        summary = format_prune_summary(results)
+        assert "5 removed" in summary
+        assert "3 removed" in summary
+        assert "Total freed" in summary
+
+
+class TestHumanSize:
+    def test_bytes(self):
+        assert _human_size(500) == "500 B"
+
+    def test_kb(self):
+        assert _human_size(2048) == "2.0 KB"
+
+    def test_mb(self):
+        assert _human_size(1024 * 1024 * 5) == "5.0 MB"
+
+    def test_gb(self):
+        assert _human_size(1024 * 1024 * 1024 * 2) == "2.0 GB"
diff --git a/tools/session_cleanup.py b/tools/session_cleanup.py
new file mode 100644
index 0000000000..1bcd9257b0
--- /dev/null
+++ b/tools/session_cleanup.py
@@ -0,0 +1,283 @@
+"""
+Session Artifact Cleanup — Prune stale disk files that accumulate over time.
+
+Hermes creates several on-disk artifacts per session that are never automatically
+cleaned up:
+
+  ~/.hermes/sessions/session_<id>.json      — CLI session transcript logs
+  ~/.hermes/sessions/request_dump_<id>.json — API debug request dumps
+  ~/.hermes/sessions/<id>.jsonl             — Gateway legacy transcript files
+  ~/.hermes/checkpoints/<hash>/             — Filesystem checkpoint shadow repos
+
+The SessionDB.prune_sessions() method only deletes DB rows. This module handles
+the disk side: identifying stale files, protecting active sessions, and reclaiming
+disk space.
+
+Inspired by qwibitai/nanoclaw#1632 (auto-prune stale session artifacts).
+"""
+
+import logging
+import os
+import shutil
+import time
+from pathlib import Path
+from typing import Dict, Optional, Set, Tuple
+
+logger = logging.getLogger(__name__)
+
+# Default retention periods (days)
+SESSION_FILE_RETENTION_DAYS = 30
+REQUEST_DUMP_RETENTION_DAYS = 7
+CHECKPOINT_RETENTION_DAYS = 14
+JSONL_TRANSCRIPT_RETENTION_DAYS = 30
+
+
+def _get_active_session_ids(db) -> Set[str]:
+    """Get session IDs that are still active (not ended) from the DB.
+
+    Returns a set of session ID strings. On error, returns an empty set
+    (fail-safe: if we can't determine active sessions, don't delete anything).
+    """
+    try:
+        rows = db.list_sessions_rich(limit=100000, include_children=True)
+        return {r["id"] for r in rows if r.get("ended_at") is None}
+    except Exception as e:
+        logger.warning("Could not fetch active sessions: %s", e)
+        return set()
+
+
+def _extract_session_id_from_filename(filename: str) -> Optional[str]:
+    """Extract the session ID from a session artifact filename.
+
+    Examples:
+        session_20260412_171123_466c.json → 20260412_171123_466c
+        request_dump_20260412_171123_466c_20260412_171125_789abc.json → 20260412_171123_466c
+        20260412_012806_2013cd04.jsonl → 20260412_012806_2013cd04
+    """
+    name = filename
+    if name.startswith("session_") and name.endswith(".json"):
+        return name[len("session_"):-len(".json")]
+    elif name.startswith("request_dump_") and name.endswith(".json"):
+        # request_dump_{session_id}_{timestamp}.json
+        # Session ID is the part between "request_dump_" and the last timestamp
+        stem = name[len("request_dump_"):-len(".json")]
+        # Session IDs look like: 20260412_171123_466c or UUID format
+        # The dump adds another _YYYYMMDD_HHMMSS_ffffff suffix
+        # Try splitting off the last 3 underscore-separated components (date_time_microseconds)
+        parts = stem.rsplit("_", 3)
+        if len(parts) >= 4:
+            return "_".join(parts[:-3])
+        return stem
+    elif name.endswith(".jsonl"):
+        return name[:-len(".jsonl")]
+    return None
+
+
+def prune_session_files(
+    sessions_dir: Path,
+    db,
+    retention_days: int = SESSION_FILE_RETENTION_DAYS,
+    dry_run: bool = False,
+) -> Tuple[int, int]:
+    """Delete stale session_*.json files from the sessions directory.
+
+    Only deletes files for sessions that are:
+    1. Older than retention_days (by file modification time)
+    2. NOT currently active in the DB
+
+    Args:
+        sessions_dir: Path to ~/.hermes/sessions/
+        db: SessionDB instance for checking active sessions
+        retention_days: Only delete files older than this many days
+        dry_run: If True, report what would be deleted without deleting
+
+    Returns:
+        (files_deleted, bytes_freed) tuple
+    """
+    if not sessions_dir.exists():
+        return 0, 0
+
+    active_ids = _get_active_session_ids(db)
+    cutoff = time.time() - (retention_days * 86400)
+    files_deleted = 0
+    bytes_freed = 0
+
+    for f in sessions_dir.iterdir():
+        if not f.is_file():
+            continue
+
+        # Skip the sessions.json state file
+        if f.name == "sessions.json":
+            continue
+
+        # Only process session files and request dumps
+        if not (f.name.startswith("session_") or f.name.startswith("request_dump_")):
+            if not f.name.endswith(".jsonl"):
+                continue
+
+        try:
+            stat = f.stat()
+        except OSError:
+            continue
+
+        # Skip files newer than retention period
+        if stat.st_mtime > cutoff:
+            continue
+
+        # Extract session ID and check if it's active
+        session_id = _extract_session_id_from_filename(f.name)
+        if session_id and session_id in active_ids:
+            continue
+
+        size = stat.st_size
+        if dry_run:
+            logger.info("Would remove: %s (%d KB)", f.name, size // 1024)
+        else:
+            try:
+                f.unlink()
+                files_deleted += 1
+                bytes_freed += size
+            except OSError as e:
+                logger.debug("Failed to remove %s: %s", f.name, e)
+
+    return files_deleted, bytes_freed
+
+
+def prune_checkpoints(
+    checkpoints_dir: Path,
+    retention_days: int = CHECKPOINT_RETENTION_DAYS,
+    dry_run: bool = False,
+) -> Tuple[int, int]:
+    """Delete stale checkpoint shadow repos.
+
+    Checkpoints are keyed by sha256(working_dir)[:16], not by session ID.
+    We use modification time as the sole criterion for staleness.
+
+    Args:
+        checkpoints_dir: Path to ~/.hermes/checkpoints/
+        retention_days: Only delete checkpoints older than this many days
+        dry_run: If True, report what would be deleted without deleting
+
+    Returns:
+        (dirs_deleted, bytes_freed) tuple
+    """
+    if not checkpoints_dir.exists():
+        return 0, 0
+
+    cutoff = time.time() - (retention_days * 86400)
+    dirs_deleted = 0
+    bytes_freed = 0
+
+    for entry in checkpoints_dir.iterdir():
+        if not entry.is_dir():
+            continue
+
+        try:
+            mtime = entry.stat().st_mtime
+        except OSError:
+            continue
+
+        if mtime > cutoff:
+            continue
+
+        # Calculate size before deletion
+        try:
+            size = sum(
+                f.stat().st_size
+                for f in entry.rglob("*")
+                if f.is_file()
+            )
+        except OSError:
+            size = 0
+
+        if dry_run:
+            logger.info("Would remove checkpoint: %s (%d KB)", entry.name, size // 1024)
+        else:
+            try:
+                shutil.rmtree(entry)
+                dirs_deleted += 1
+                bytes_freed += size
+            except OSError as e:
+                logger.debug("Failed to remove checkpoint %s: %s", entry.name, e)
+
+    return dirs_deleted, bytes_freed
+
+
+def prune_all_artifacts(
+    hermes_home: Path,
+    db,
+    session_retention_days: int = SESSION_FILE_RETENTION_DAYS,
+    checkpoint_retention_days: int = CHECKPOINT_RETENTION_DAYS,
+    dry_run: bool = False,
+) -> Dict[str, Tuple[int, int]]:
+    """Prune all stale session artifacts from disk.
+
+    This is the main entry point for both the CLI command and automated cleanup.
+
+    Args:
+        hermes_home: Path to ~/.hermes/
+        db: SessionDB instance
+        session_retention_days: Retention for session files and request dumps
+        checkpoint_retention_days: Retention for checkpoint directories
+        dry_run: If True, report what would be deleted without deleting
+
+    Returns:
+        Dict mapping artifact type to (count_deleted, bytes_freed):
+        {
+            "session_files": (N, bytes),
+            "checkpoints": (N, bytes),
+        }
+    """
+    results = {}
+
+    sessions_dir = hermes_home / "sessions"
+    files_del, files_bytes = prune_session_files(
+        sessions_dir, db,
+        retention_days=session_retention_days,
+        dry_run=dry_run,
+    )
+    results["session_files"] = (files_del, files_bytes)
+
+    checkpoints_dir = hermes_home / "checkpoints"
+    cp_del, cp_bytes = prune_checkpoints(
+        checkpoints_dir,
+        retention_days=checkpoint_retention_days,
+        dry_run=dry_run,
+    )
+    results["checkpoints"] = (cp_del, cp_bytes)
+
+    return results
+
+
+def format_prune_summary(results: Dict[str, Tuple[int, int]]) -> str:
+    """Format prune results as a human-readable summary."""
+    lines = []
+    total_freed = 0
+
+    files_del, files_bytes = results.get("session_files", (0, 0))
+    if files_del:
+        lines.append(f"  Session files: {files_del} removed ({_human_size(files_bytes)})")
+        total_freed += files_bytes
+
+    cp_del, cp_bytes = results.get("checkpoints", (0, 0))
+    if cp_del:
+        lines.append(f"  Checkpoints:   {cp_del} removed ({_human_size(cp_bytes)})")
+        total_freed += cp_bytes
+
+    if not lines:
+        return "No stale artifacts found."
+
+    lines.append(f"  Total freed:   {_human_size(total_freed)}")
+    return "\n".join(lines)
+
+
+def _human_size(size_bytes: int) -> str:
+    """Convert bytes to human-readable size string."""
+    if size_bytes < 1024:
+        return f"{size_bytes} B"
+    elif size_bytes < 1024 * 1024:
+        return f"{size_bytes / 1024:.1f} KB"
+    elif size_bytes < 1024 * 1024 * 1024:
+        return f"{size_bytes / (1024 * 1024):.1f} MB"
+    else:
+        return f"{size_bytes / (1024 * 1024 * 1024):.1f} GB"