diff --git a/pkgs/clan-cli/clan_cli/clan_uri.py b/pkgs/clan-cli/clan_cli/clan_uri.py
index 3102b5ff..aaeac225 100644
--- a/pkgs/clan-cli/clan_cli/clan_uri.py
+++ b/pkgs/clan-cli/clan_cli/clan_uri.py
@@ -40,6 +40,7 @@ class ClanParameters:
 class ClanURI:
     # Initialize the class with a clan:// URI
     def __init__(self, uri: str) -> None:
+
         # Check if the URI starts with clan://
         if uri.startswith("clan://"):
             self._nested_uri = uri[7:]
diff --git a/pkgs/clan-cli/clan_cli/flakes/inspect.py b/pkgs/clan-cli/clan_cli/flakes/inspect.py
index 53cf72d6..42f5ec91 100644
--- a/pkgs/clan-cli/clan_cli/flakes/inspect.py
+++ b/pkgs/clan-cli/clan_cli/flakes/inspect.py
@@ -13,6 +13,7 @@ class FlakeConfig:
     flake_url: str | Path
     flake_attr: str
 
+    nar_hash: str
     icon: str | None
     description: str | None
     last_updated: str
@@ -29,7 +30,7 @@ def inspect_flake(flake_url: str | Path, flake_attr: str) -> FlakeConfig:
         ]
     )
 
-    proc = subprocess.run(cmd, check=True, text=True, stdout=subprocess.PIPE)
+    proc = subprocess.run(cmd, text=True, capture_output=True)
     assert proc.stdout is not None
     if proc.returncode != 0:
         raise ClanError(
@@ -38,6 +39,8 @@ command: {shlex.join(cmd)}
 exit code: {proc.returncode}
 stdout:
 {proc.stdout}
+stderr:
+{proc.stderr}
 """
         )
     res = proc.stdout.strip()
@@ -51,6 +54,7 @@ stdout:
     return FlakeConfig(
         flake_url=flake_url,
         flake_attr=flake_attr,
+        nar_hash=meta["locked"]["narHash"],
         icon=icon_path,
         description=meta.get("description"),
         last_updated=meta["lastModified"],
diff --git a/pkgs/clan-cli/clan_cli/history/add.py b/pkgs/clan-cli/clan_cli/history/add.py
index d40520f9..23bf41dc 100644
--- a/pkgs/clan-cli/clan_cli/history/add.py
+++ b/pkgs/clan-cli/clan_cli/history/add.py
@@ -3,7 +3,6 @@ import argparse
 import dataclasses
 import datetime
 import json
-import os
 from pathlib import Path
 from typing import Any
 
@@ -22,11 +21,13 @@ class EnhancedJSONEncoder(json.JSONEncoder):
 
 @dataclasses.dataclass
 class HistoryEntry:
-    path: str
     last_used: str
-    dir_datetime: str
     flake: FlakeConfig
 
+    def __post_init__(self) -> None:
+        if isinstance(self.flake, dict):
+            self.flake = FlakeConfig(**self.flake)
+
 
 def list_history() -> list[HistoryEntry]:
     logs: list[HistoryEntry] = []
@@ -45,35 +46,26 @@ def list_history() -> list[HistoryEntry]:
     return logs
 
 
-def get_dir_time(path: Path) -> str:
-    # Get the last modified dir time in seconds
-    dir_mtime = os.path.getmtime(path)
-    dir_datetime = datetime.datetime.fromtimestamp(dir_mtime).isoformat()
-    return dir_datetime
-
-
 def add_history(path: Path) -> list[HistoryEntry]:
     user_history_file().parent.mkdir(parents=True, exist_ok=True)
     logs = list_history()
     found = False
 
     for entry in logs:
-        if entry.path == str(path):
+        if entry.flake.flake_url == str(path):
             found = True
             entry.last_used = datetime.datetime.now().isoformat()
 
+        if found:
+            break
+
     flake = inspect_flake(path, "defaultVM")
     flake.flake_url = str(flake.flake_url)
-    dir_datetime = get_dir_time(path)
-
     history = HistoryEntry(
         flake=flake,
-        dir_datetime=dir_datetime,
-        path=str(path),
         last_used=datetime.datetime.now().isoformat(),
     )
-    if not found:
-        logs.append(history)
+    logs.append(history)
 
     with locked_open(user_history_file(), "w+") as f:
         f.write(json.dumps(logs, cls=EnhancedJSONEncoder, indent=4))
diff --git a/pkgs/clan-cli/clan_cli/history/list.py b/pkgs/clan-cli/clan_cli/history/list.py
index aae04f6c..f9c89f40 100644
--- a/pkgs/clan-cli/clan_cli/history/list.py
+++ b/pkgs/clan-cli/clan_cli/history/list.py
@@ -6,7 +6,7 @@ from .add import list_history
 
 def list_history_command(args: argparse.Namespace) -> None:
     for history_entry in list_history():
-        print(history_entry.path)
+        print(history_entry.flake.flake_url)
 
 
 # takes a (sub)parser and configures it
diff --git a/pkgs/clan-cli/clan_cli/history/update.py b/pkgs/clan-cli/clan_cli/history/update.py
index 99c2dab6..9f1202e6 100644
--- a/pkgs/clan-cli/clan_cli/history/update.py
+++ b/pkgs/clan-cli/clan_cli/history/update.py
@@ -3,11 +3,11 @@ import argparse
 import copy
 import datetime
 import json
-from pathlib import Path
 
 from ..dirs import user_history_file
 from ..locked_open import locked_open
-from .add import EnhancedJSONEncoder, HistoryEntry, get_dir_time, list_history
+from ..nix import nix_metadata
+from .add import EnhancedJSONEncoder, HistoryEntry, list_history
 
 
 def update_history() -> list[HistoryEntry]:
@@ -16,11 +16,17 @@ def update_history() -> list[HistoryEntry]:
     new_logs = []
     for entry in logs:
         new_entry = copy.deepcopy(entry)
-        new_time = get_dir_time(Path(entry.path))
-        if new_time != entry.dir_datetime:
-            print(f"Updating {entry.path} from {entry.dir_datetime} to {new_time}")
-            new_entry.dir_datetime = new_time
+
+        meta = nix_metadata(entry.flake.flake_url)
+        new_hash = meta["locked"]["narHash"]
+        if new_hash != entry.flake.nar_hash:
+            print(
+                f"Updating {entry.flake.flake_url} from {entry.flake.nar_hash} to {new_hash}"
+            )
             new_entry.last_used = datetime.datetime.now().isoformat()
+            new_entry.flake.nar_hash = new_hash
+
+        # TODO: Delete stale entries
         new_logs.append(new_entry)
 
     with locked_open(user_history_file(), "w+") as f:
diff --git a/pkgs/clan-cli/clan_cli/machines/list.py b/pkgs/clan-cli/clan_cli/machines/list.py
index 371be2c8..8ee271a7 100644
--- a/pkgs/clan-cli/clan_cli/machines/list.py
+++ b/pkgs/clan-cli/clan_cli/machines/list.py
@@ -1,24 +1,42 @@
 import argparse
+import json
 import logging
-import os
+import shlex
+import subprocess
 from pathlib import Path
 
-from ..dirs import machines_dir
-from .types import validate_hostname
+from ..errors import ClanError
+from ..nix import nix_config, nix_eval
 
 log = logging.getLogger(__name__)
 
 
 def list_machines(flake_dir: Path) -> list[str]:
-    path = machines_dir(flake_dir)
-    log.debug(f"Listing machines in {path}")
-    if not path.exists():
-        return []
-    objs: list[str] = []
-    for f in os.listdir(path):
-        if validate_hostname(f):
-            objs.append(f)
-    return objs
+    config = nix_config()
+    system = config["system"]
+    cmd = nix_eval(
+        [
+            f"{flake_dir}#clanInternals.machines.{system}",
+            "--apply",
+            "builtins.attrNames",
+            "--json",
+        ]
+    )
+    proc = subprocess.run(cmd, text=True, capture_output=True)
+    assert proc.stdout is not None
+    if proc.returncode != 0:
+        raise ClanError(
+            f"""
+command: {shlex.join(cmd)}
+exit code: {proc.returncode}
+stdout:
+{proc.stdout}
+stderr:
+{proc.stderr}
+"""
+        )
+    res = proc.stdout.strip()
+    return json.loads(res)
 
 
 def list_command(args: argparse.Namespace) -> None:
diff --git a/pkgs/clan-cli/tests/test_history_cli.py b/pkgs/clan-cli/tests/test_history_cli.py
index ed793084..69f14098 100644
--- a/pkgs/clan-cli/tests/test_history_cli.py
+++ b/pkgs/clan-cli/tests/test_history_cli.py
@@ -21,13 +21,13 @@ def test_history_add(
         "add",
         str(test_flake.path),
     ]
-
+    breakpoint()
     cli.run(cmd)
 
     history_file = user_history_file()
     assert history_file.exists()
     history = [HistoryEntry(**entry) for entry in json.loads(open(history_file).read())]
-    assert history[0].path == str(test_flake.path)
+    assert history[0].flake.flake_url == str(test_flake.path)
 
 
 def test_history_list(
diff --git a/pkgs/clan-vm-manager/clan-vm-manager.code-workspace b/pkgs/clan-vm-manager/clan-vm-manager.code-workspace
index 6f28f07d..307d1d20 100644
--- a/pkgs/clan-vm-manager/clan-vm-manager.code-workspace
+++ b/pkgs/clan-vm-manager/clan-vm-manager.code-workspace
@@ -11,6 +11,22 @@
 		}
 	],
 	"settings": {
-		"python.linting.mypyEnabled": true
+		"python.linting.mypyEnabled": true,
+		"files.exclude": {
+			"**/.direnv": true,
+			"**/.mypy_cache": true,
+			"**/.ruff_cache": true,
+			"**/.hypothesis": true,
+			"**/__pycache__": true,
+			"**/.reports": true
+		},
+		"search.exclude": {
+			"**/.direnv": true,
+			"**/.mypy_cache": true,
+			"**/.ruff_cache": true,
+			"**/.hypothesis": true,
+			"**/__pycache__": true,
+			"**/.reports": true
+		}
 	}
 }
\ No newline at end of file