diff --git a/pkgs/clan-app/shell.nix b/pkgs/clan-app/shell.nix
index 34f96b6b0..667f82e70 100644
--- a/pkgs/clan-app/shell.nix
+++ b/pkgs/clan-app/shell.nix
@@ -51,6 +51,9 @@ mkShell {
     export GIT_ROOT=$(git rev-parse --show-toplevel)
     export PKG_ROOT=$GIT_ROOT/pkgs/clan-app
 
+    # Add current package to PYTHONPATH
+    export PYTHONPATH="$PKG_ROOT''${PYTHONPATH:+:$PYTHONPATH:}"
+
     # Add clan-app command to PATH
     export PATH="$PKG_ROOT/bin":"$PATH"
 
diff --git a/pkgs/clan-app/tests/conftest.py b/pkgs/clan-app/tests/conftest.py
index 244f5bfe8..9f107889f 100644
--- a/pkgs/clan-app/tests/conftest.py
+++ b/pkgs/clan-app/tests/conftest.py
@@ -1,14 +1,10 @@
 import subprocess
-import sys
 from pathlib import Path
 
 import pytest
 from clan_cli.custom_logger import setup_logging
 from clan_cli.nix import nix_shell
 
-sys.path.append(str(Path(__file__).parent / "helpers"))
-sys.path.append(str(Path(__file__).parent.parent))  # Also add clan app to PYTHONPATH
-
 pytest_plugins = [
     "temporary_dir",
     "root",
diff --git a/pkgs/clan-app/tests/helpers/__init__.py b/pkgs/clan-app/tests/helpers/__init__.py
new file mode 100644
index 000000000..e69de29bb
diff --git a/pkgs/clan-app/tests/test_cli.py b/pkgs/clan-app/tests/test_cli.py
index 182098859..64cc88919 100644
--- a/pkgs/clan-app/tests/test_cli.py
+++ b/pkgs/clan-app/tests/test_cli.py
@@ -1,5 +1,5 @@
 import pytest
-from cli import Cli
+from helpers.cli import Cli
 
 
 def test_help(capfd: pytest.CaptureFixture) -> None:
diff --git a/pkgs/clan-cli/shell.nix b/pkgs/clan-cli/shell.nix
index 3949685d4..53f926021 100644
--- a/pkgs/clan-cli/shell.nix
+++ b/pkgs/clan-cli/shell.nix
@@ -31,6 +31,9 @@ mkShell {
     export GIT_ROOT="$(git rev-parse --show-toplevel)"
     export PKG_ROOT="$GIT_ROOT/pkgs/clan-cli"
 
+    # Add current package to PYTHONPATH
+    export PYTHONPATH="$PKG_ROOT''${PYTHONPATH:+:$PYTHONPATH:}"
+
     # Add clan command to PATH
     export PATH="$PKG_ROOT/bin":"$PATH"
 
diff --git a/pkgs/clan-cli/tests/conftest.py b/pkgs/clan-cli/tests/conftest.py
index 5ec8735fc..a0374aeea 100644
--- a/pkgs/clan-cli/tests/conftest.py
+++ b/pkgs/clan-cli/tests/conftest.py
@@ -1,14 +1,8 @@
-import os
 import subprocess
-import sys
 from pathlib import Path
 
 import pytest
 
-sys.path.append(os.path.join(os.path.dirname(__file__), "helpers"))
-sys.path.append(str(Path(__file__).parent.parent))  # Also add clan_cli to PYTHONPATH
-
-
 from clan_cli.custom_logger import setup_logging
 from clan_cli.nix import nix_shell
 
diff --git a/pkgs/clan-cli/tests/helpers/__init__.py b/pkgs/clan-cli/tests/helpers/__init__.py
new file mode 100644
index 000000000..e69de29bb
diff --git a/pkgs/clan-cli/tests/test_backups.py b/pkgs/clan-cli/tests/test_backups.py
index 16ec42ac9..8ac99c39c 100644
--- a/pkgs/clan-cli/tests/test_backups.py
+++ b/pkgs/clan-cli/tests/test_backups.py
@@ -1,6 +1,6 @@
 import pytest
-from cli import Cli
 from fixtures_flakes import FlakeForTest
+from helpers.cli import Cli
 
 
 @pytest.mark.impure
diff --git a/pkgs/clan-cli/tests/test_cli.py b/pkgs/clan-cli/tests/test_cli.py
index 24cbd5464..87a6eaac7 100644
--- a/pkgs/clan-cli/tests/test_cli.py
+++ b/pkgs/clan-cli/tests/test_cli.py
@@ -1,5 +1,5 @@
 import pytest
-from cli import Cli
+from helpers.cli import Cli
 
 
 def test_help(capsys: pytest.CaptureFixture) -> None:
diff --git a/pkgs/clan-cli/tests/test_config.py b/pkgs/clan-cli/tests/test_config.py
index 985b15c16..508f361ae 100644
--- a/pkgs/clan-cli/tests/test_config.py
+++ b/pkgs/clan-cli/tests/test_config.py
@@ -1,8 +1,8 @@
 from pathlib import Path
 
 import pytest
-from cli import Cli
 from fixtures_flakes import FlakeForTest
+from helpers.cli import Cli
 
 from clan_cli import config
 from clan_cli.config import parsing
diff --git a/pkgs/clan-cli/tests/test_create_flake.py b/pkgs/clan-cli/tests/test_create_flake.py
index dc5a6dc8e..2db3dae46 100644
--- a/pkgs/clan-cli/tests/test_create_flake.py
+++ b/pkgs/clan-cli/tests/test_create_flake.py
@@ -3,7 +3,7 @@ import subprocess
 from pathlib import Path
 
 import pytest
-from cli import Cli
+from helpers.cli import Cli
 
 
 @pytest.fixture
diff --git a/pkgs/clan-cli/tests/test_flakes_cli.py b/pkgs/clan-cli/tests/test_flakes_cli.py
index 34e4f3436..e6c6a4421 100644
--- a/pkgs/clan-cli/tests/test_flakes_cli.py
+++ b/pkgs/clan-cli/tests/test_flakes_cli.py
@@ -1,8 +1,8 @@
 from typing import TYPE_CHECKING
 
 import pytest
-from cli import Cli
 from fixtures_flakes import FlakeForTest
+from helpers.cli import Cli
 
 if TYPE_CHECKING:
     pass
diff --git a/pkgs/clan-cli/tests/test_history_cli.py b/pkgs/clan-cli/tests/test_history_cli.py
index 20523889a..284c302e7 100644
--- a/pkgs/clan-cli/tests/test_history_cli.py
+++ b/pkgs/clan-cli/tests/test_history_cli.py
@@ -2,8 +2,8 @@ import json
 from typing import TYPE_CHECKING
 
 import pytest
-from cli import Cli
 from fixtures_flakes import FlakeForTest
+from helpers.cli import Cli
 from pytest import CaptureFixture
 
 from clan_cli.dirs import user_history_file
diff --git a/pkgs/clan-cli/tests/test_import_sops_cli.py b/pkgs/clan-cli/tests/test_import_sops_cli.py
index 17a9a5a69..52770dfba 100644
--- a/pkgs/clan-cli/tests/test_import_sops_cli.py
+++ b/pkgs/clan-cli/tests/test_import_sops_cli.py
@@ -2,8 +2,8 @@ from pathlib import Path
 from typing import TYPE_CHECKING
 
 import pytest
-from cli import Cli
 from fixtures_flakes import FlakeForTest
+from helpers.cli import Cli
 
 if TYPE_CHECKING:
     from age_keys import KeyPair
diff --git a/pkgs/clan-cli/tests/test_machines_cli.py b/pkgs/clan-cli/tests/test_machines_cli.py
index c4e483d42..399f0a3af 100644
--- a/pkgs/clan-cli/tests/test_machines_cli.py
+++ b/pkgs/clan-cli/tests/test_machines_cli.py
@@ -1,6 +1,6 @@
 import pytest
-from cli import Cli
 from fixtures_flakes import FlakeForTest
+from helpers.cli import Cli
 
 
 @pytest.mark.impure
diff --git a/pkgs/clan-cli/tests/test_modules.py b/pkgs/clan-cli/tests/test_modules.py
index 4f65e2a77..7c644dd1a 100644
--- a/pkgs/clan-cli/tests/test_modules.py
+++ b/pkgs/clan-cli/tests/test_modules.py
@@ -13,7 +13,7 @@ from clan_cli.nix import nix_eval, run_no_stdout
 if TYPE_CHECKING:
     from age_keys import KeyPair
 
-from cli import Cli
+from helpers.cli import Cli
 
 from clan_cli.machines.facts import machine_get_fact
 
diff --git a/pkgs/clan-cli/tests/test_secrets_cli.py b/pkgs/clan-cli/tests/test_secrets_cli.py
index 05cf7a8c6..c14022096 100644
--- a/pkgs/clan-cli/tests/test_secrets_cli.py
+++ b/pkgs/clan-cli/tests/test_secrets_cli.py
@@ -5,8 +5,8 @@ from contextlib import contextmanager
 from typing import TYPE_CHECKING
 
 import pytest
-from cli import Cli
 from fixtures_flakes import FlakeForTest
+from helpers.cli import Cli
 
 from clan_cli.errors import ClanError
 
diff --git a/pkgs/clan-cli/tests/test_secrets_generate.py b/pkgs/clan-cli/tests/test_secrets_generate.py
index 63d47a457..41ce3436a 100644
--- a/pkgs/clan-cli/tests/test_secrets_generate.py
+++ b/pkgs/clan-cli/tests/test_secrets_generate.py
@@ -2,9 +2,9 @@ import ipaddress
 from typing import TYPE_CHECKING
 
 import pytest
-from cli import Cli
 from fixtures_flakes import FlakeForTest
-from validator import is_valid_age_key, is_valid_ssh_key
+from helpers.cli import Cli
+from helpers.validator import is_valid_age_key, is_valid_ssh_key
 
 from clan_cli.clan_uri import FlakeId
 from clan_cli.facts.secret_modules.sops import SecretStore
diff --git a/pkgs/clan-cli/tests/test_secrets_password_store.py b/pkgs/clan-cli/tests/test_secrets_password_store.py
index ef9ab23ff..2f813b1a2 100644
--- a/pkgs/clan-cli/tests/test_secrets_password_store.py
+++ b/pkgs/clan-cli/tests/test_secrets_password_store.py
@@ -2,9 +2,9 @@ import subprocess
 from pathlib import Path
 
 import pytest
-from cli import Cli
 from fixtures_flakes import FlakeForTest
-from validator import is_valid_ssh_key
+from helpers.cli import Cli
+from helpers.validator import is_valid_ssh_key
 
 from clan_cli.clan_uri import FlakeId
 from clan_cli.facts.secret_modules.password_store import SecretStore
diff --git a/pkgs/clan-cli/tests/test_secrets_upload.py b/pkgs/clan-cli/tests/test_secrets_upload.py
index fa829324b..b246f35c7 100644
--- a/pkgs/clan-cli/tests/test_secrets_upload.py
+++ b/pkgs/clan-cli/tests/test_secrets_upload.py
@@ -1,8 +1,8 @@
 from typing import TYPE_CHECKING
 
 import pytest
-from cli import Cli
 from fixtures_flakes import FlakeForTest
+from helpers.cli import Cli
 
 from clan_cli.ssh import HostGroup
 
diff --git a/pkgs/clan-cli/tests/test_vms_cli.py b/pkgs/clan-cli/tests/test_vms_cli.py
index 73a614f0e..fa654ce99 100644
--- a/pkgs/clan-cli/tests/test_vms_cli.py
+++ b/pkgs/clan-cli/tests/test_vms_cli.py
@@ -7,8 +7,8 @@ from time import sleep
 from typing import TYPE_CHECKING
 
 import pytest
-from cli import Cli
 from fixtures_flakes import FlakeForTest, generate_flake
+from helpers.cli import Cli
 from root import CLAN_CORE
 
 from clan_cli.dirs import vm_state_dir