Merge pull request 'age plugin support' (#3322) from feat/age-plugin-support into main

Reviewed-on: https://git.clan.lol/clan/clan-core/pulls/3322

docs/site/getting-started/secrets.md

@@ -1,18 +1,19 @@
 
 Clan enables encryption of secrets (such as passwords & keys) ensuring security and ease-of-use among users.
 
-By default Clan utilizes the [sops](https://github.com/getsops/sops) format and integrates with [sops-nix](https://github.com/Mic92/sops-nix) on NixOS machines.
+By default, Clan uses the [sops](https://github.com/getsops/sops) format
+and integrates with [sops-nix](https://github.com/Mic92/sops-nix) on NixOS machines.
 Clan can also be configured to be used with other secret store [backends](https://docs.clan.lol/reference/clan-core/vars/#clan.core.vars.settings.secretStore).
 
 This guide will walk you through:
 
-- **Creating a Keypair for Your User**: Learn how to generate a keypair for $USER to securely control all secrets.
+- **Creating a Keypair for Your User**: Learn how to generate a keypair for `$USER` to securely control all secrets.
 - **Creating Your First Secret**: Step-by-step instructions on creating your initial secret.
 - **Assigning Machine Access to the Secret**: Understand how to grant a machine access to the newly created secret.
 
 ## Create Your Admin Keypair
 
-To get started, you'll need to create **Your admin keypair**.
+To get started, you'll need to create **your admin keypair**.
 
 !!! info
     Don't worry — if you've already made one before, this step won't change or overwrite it.
@@ -34,9 +35,78 @@ Also add your age public key to the repository with 'clan secrets users add YOUR
     Make sure to keep a safe backup of the private key you've just created.
     If it's lost, you won't be able to get to your secrets anymore because they all need the admin key to be unlocked.
 
+If you already have an [age] secret key and want to use that instead, you can simply edit `~/.config/sops/age/keys.txt`:
+
+```title="~/.config/sops/age/keys.txt"
+AGE-SECRET-KEY-13GWMK0KNNKXPTJ8KQ9LPSQZU7G3KU8LZDW474NX3D956GGVFAZRQTAE3F4
+```
+
+Alternatively, you can provide your [age] secret key as an environment variable `SOPS_AGE_KEY`, or in a different file
+using `SOPS_AGE_KEY_FILE`.
+For more information see the [SOPS] guide on [encrypting with age].
+
 !!! note
     It's safe to add any secrets created by the clan CLI and placed in your repository to version control systems like `git`.
 
+### Using Age Plugins
+
+If you wish to use a key generated using an [age plugin] as your admin key, extra care is needed.
+
+You must **precede your secret key with a comment that contains its corresponding recipient**.
+
+This is usually output as part of the generation process
+and is only required because there is no unified mechanism for recovering a recipient from a plugin secret key.
+
+Here is an example:
+
+```title="~/.config/sops/age/keys.txt"
+# public key: age1zdy49ek6z60q9r34vf5mmzkx6u43pr9haqdh5lqdg7fh5tpwlfwqea356l
+AGE-PLUGIN-FIDO2-HMAC-1QQPQZRFR7ZZ2WCV...
+```
+
+!!! note
+    The comment that precedes the plugin secret key need only contain the recipient.
+    Any other text is ignored.
+
+    In the example above, you can specify `# recipient: age1zdy...`, `# public: age1zdy....` or even
+    just `# age1zdy....`
+
+You will need to add an entry into your `flake.nix` to ensure that the necessary `age` plugins
+are loaded when using Clan:
+
+```nix title="flake.nix"
+{
+  inputs.clan-core.url = "https://git.clan.lol/clan/clan-core/archive/main.tar.gz";
+  inputs.nixpkgs.follows = "clan-core/nixpkgs";
+
+  outputs =
+    { self, clan-core, ... }:
+    let
+      clan = clan-core.clanLib.buildClan {
+        inherit self;
+
+        meta.name = "myclan";
+
+        # Add Yubikey and FIDO2 HMAC plugins
+        # Note: the plugins listed here must be available in nixpkgs.
+        secrets.age.plugins = [
+          "age-plugin-yubikey"
+          "age-plugin-fido2-hmac"
+        ];
+
+        machines = {
+          # elided for brevity
+        };
+      };
+    in
+    {
+      inherit (clan) nixosConfigurations clanInternals;
+
+      # elided for brevity
+    };
+}
+```
+
 ### Add Your Public Key(s)
 
 ```console
@@ -70,7 +140,7 @@ If you followed the quickstart tutorial all necessary secrets are initialized at
 You can list keys for your user with `clan secrets users get $USER`:
 
 ```console
-❯ bin/clan secrets users get alice
+clan secrets users get alice
 
 [
   {
@@ -97,3 +167,8 @@ To remove a key from your user:
 ```console
 clan secrets users remove-key $USER --age-key <your_public_key>
 ```
+
+[age]: https://github.com/FiloSottile/age
+[age plugin]: https://github.com/FiloSottile/awesome-age?tab=readme-ov-file#plugins
+[sops]: https://github.com/getsops/sops
+[encrypting with age]: https://github.com/getsops/sops?tab=readme-ov-file#encrypting-using-age

lib/build-clan/interface.nix

@@ -108,6 +108,14 @@ in
       default = { };
     };
 
+    secrets = lib.mkOption {
+      type = types.submodule { imports = [ ./secrets/interface.nix ]; };
+      description = ''
+        Secrets related options such as AGE plugins required to encrypt/decrypt secrets using the CLI.
+      '';
+      default = { };
+    };
+
     pkgsForSystem = lib.mkOption {
       type = types.functionTo (types.nullOr types.attrs);
       default = _system: null;
@@ -165,6 +173,7 @@ in
           clanModules = lib.mkOption { type = lib.types.raw; };
           source = lib.mkOption { type = lib.types.raw; };
           meta = lib.mkOption { type = lib.types.raw; };
+          secrets = lib.mkOption { type = lib.types.raw; };
           clanLib = lib.mkOption { type = lib.types.raw; };
           all-machines-json = lib.mkOption { type = lib.types.raw; };
           machines = lib.mkOption { type = lib.types.raw; };

lib/build-clan/module.nix

@@ -219,6 +219,7 @@ in
     templates = config.templates;
     inventory = config.inventory;
     meta = config.inventory.meta;
+    secrets = config.secrets;
 
     source = "${clan-core}";
 

lib/build-clan/secrets/interface.nix

@@ -0,0 +1,18 @@
+{
+  lib,
+  ...
+}:
+let
+  inherit (lib) types;
+in
+{
+  options = {
+    age.plugins = lib.mkOption {
+      type = types.listOf (types.strMatching "age-plugin-.*");
+      default = [ ];
+      description = ''
+        A list of age plugins which must be available in the shell when encrypting and decrypting secrets.
+      '';
+    };
+  };
+}

pkgs/clan-cli/clan_cli/nix/allowed-packages.json

@@ -1,5 +1,11 @@
 [
   "age",
+  "age-plugin-fido2-hmac",
+  "age-plugin-ledger",
+  "age-plugin-se",
+  "age-plugin-sss",
+  "age-plugin-tpm",
+  "age-plugin-yubikey",
   "avahi",
   "bash",
   "bubblewrap",

pkgs/clan-cli/clan_cli/secrets/groups.py

@@ -240,6 +240,7 @@ def add_group_argument(parser: argparse.ArgumentParser) -> None:
 
 def add_secret(flake_dir: Path, group: str, name: str) -> None:
     secrets.allow_member(
+        flake_dir,
         secrets.groups_folder(sops_secrets_folder(flake_dir) / name),
         sops_groups_folder(flake_dir),
         group,
@@ -267,7 +268,7 @@ def add_secret_command(args: argparse.Namespace) -> None:
 
 def remove_secret(flake_dir: Path, group: str, name: str) -> None:
     updated_paths = secrets.disallow_member(
-        secrets.groups_folder(sops_secrets_folder(flake_dir) / name), group
+        flake_dir, secrets.groups_folder(sops_secrets_folder(flake_dir) / name), group
     )
     commit_files(
         updated_paths,

pkgs/clan-cli/clan_cli/secrets/machines.py

@@ -74,6 +74,7 @@ def list_sops_machines(flake_dir: Path) -> list[str]:
 
 def add_secret(flake_dir: Path, machine: str, secret_path: Path) -> None:
     paths = secrets.allow_member(
+        flake_dir,
         secrets.machines_folder(secret_path),
         sops_machines_folder(flake_dir),
         machine,
@@ -87,7 +88,9 @@ def add_secret(flake_dir: Path, machine: str, secret_path: Path) -> None:
 
 def remove_secret(flake_dir: Path, machine: str, secret: str) -> None:
     updated_paths = secrets.disallow_member(
-        secrets.machines_folder(sops_secrets_folder(flake_dir) / secret), machine
+        flake_dir,
+        secrets.machines_folder(sops_secrets_folder(flake_dir) / secret),
+        machine,
     )
     commit_files(
         updated_paths,

pkgs/clan-cli/clan_cli/secrets/secrets.py

@@ -86,6 +86,7 @@ def update_secrets(
         changed_files.extend(cleanup_dangling_symlinks(path / "machines"))
         changed_files.extend(
             update_keys(
+                flake_dir,
                 path,
                 collect_keys_for_path(path),
             )
@@ -155,16 +156,14 @@ def encrypt_secret(
     if add_users is None:
         add_users = []
 
-    keys = sops.ensure_admin_public_key(flake_dir)
+    admin_keys = sops.ensure_admin_public_keys(flake_dir)
 
-    if not keys:
+    if not admin_keys:
         # todo double check the correct command to run
         msg = "No keys found. Please run 'clan secrets add-key' to add a key."
         raise ClanError(msg)
 
-    username = next(iter(keys)).username
+    username = next(iter(admin_keys)).username
-
-    recipient_keys = set()
 
     # encrypt_secret can be called before the secret has been created
     # so don't try to call sops.update_keys on a non-existent file:
@@ -174,6 +173,7 @@ def encrypt_secret(
     for user in add_users:
         files_to_commit.extend(
             allow_member(
+                flake_dir,
                 users_folder(secret_path),
                 sops_users_folder(flake_dir),
                 user,
@@ -184,6 +184,7 @@ def encrypt_secret(
     for machine in add_machines:
         files_to_commit.extend(
             allow_member(
+                flake_dir,
                 machines_folder(secret_path),
                 sops_machines_folder(flake_dir),
                 machine,
@@ -194,6 +195,7 @@ def encrypt_secret(
     for group in add_groups:
         files_to_commit.extend(
             allow_member(
+                flake_dir,
                 groups_folder(secret_path),
                 sops_groups_folder(flake_dir),
                 group,
@@ -203,11 +205,12 @@ def encrypt_secret(
 
     recipient_keys = collect_keys_for_path(secret_path)
 
-    if not keys.intersection(recipient_keys):
+    if admin_keys not in recipient_keys:
-        recipient_keys.update(keys)
+        recipient_keys.update(admin_keys)
 
         files_to_commit.extend(
             allow_member(
+                flake_dir,
                 users_folder(secret_path),
                 sops_users_folder(flake_dir),
                 username,
@@ -216,7 +219,7 @@ def encrypt_secret(
         )
 
     secret_path = secret_path / "secret"
-    encrypt_file(secret_path, value, sorted(recipient_keys))
+    encrypt_file(flake_dir, secret_path, value, sorted(recipient_keys))
     files_to_commit.append(secret_path)
     if git_commit:
         commit_files(
@@ -276,7 +279,11 @@ def list_directory(directory: Path) -> str:
 
 
 def allow_member(
-    group_folder: Path, source_folder: Path, name: str, do_update_keys: bool = True
+    flake_dir: str | Path,
+    group_folder: Path,
+    source_folder: Path,
+    name: str,
+    do_update_keys: bool = True,
 ) -> list[Path]:
     source = source_folder / name
     if not source.exists():
@@ -299,6 +306,7 @@ def allow_member(
     if do_update_keys:
         changed.extend(
             update_keys(
+                flake_dir,
                 group_folder.parent,
                 collect_keys_for_path(group_folder.parent),
             )
@@ -306,7 +314,7 @@ def allow_member(
     return changed
 
 
-def disallow_member(group_folder: Path, name: str) -> list[Path]:
+def disallow_member(flake_dir: str | Path, group_folder: Path, name: str) -> list[Path]:
     target = group_folder / name
     if not target.exists():
         msg = f"{name} does not exist in group in {group_folder}: "
@@ -326,7 +334,9 @@ def disallow_member(group_folder: Path, name: str) -> list[Path]:
     if next(group_folder.parent.iterdir(), None) is None:
         group_folder.parent.rmdir()
 
-    return update_keys(target.parent.parent, collect_keys_for_path(group_folder.parent))
+    return update_keys(
+        flake_dir, target.parent.parent, collect_keys_for_path(group_folder.parent)
+    )
 
 
 def has_secret(secret_path: Path) -> bool:
@@ -366,7 +376,7 @@ def decrypt_secret(flake_dir: Path, secret_path: Path) -> str:
     if not path.exists():
         msg = f"Secret '{secret_path!s}' does not exist"
         raise ClanError(msg)
-    return decrypt_file(path)
+    return decrypt_file(flake_dir, path)
 
 
 def get_command(args: argparse.Namespace) -> None:

pkgs/clan-cli/clan_cli/secrets/sops.py

@@ -4,6 +4,7 @@ import io
 import json
 import logging
 import os
+import re
 import shutil
 import subprocess
 from collections.abc import Iterable, Sequence
@@ -17,9 +18,11 @@ from clan_lib.api import API
 from clan_cli.cmd import Log, RunOpts, run
 from clan_cli.dirs import user_config_dir
 from clan_cli.errors import ClanError
-from clan_cli.nix import nix_shell
+from clan_cli.nix import nix_eval, nix_shell
 
-from .folders import sops_machines_folder, sops_users_folder
+from .folders import sops_users_folder
+
+AGE_RECIPIENT_REGEX = re.compile(r"^.*((age1|ssh-(rsa|ed25519) ).*?)(\s|$)")
 
 log = logging.getLogger(__name__)
 
@@ -55,14 +58,20 @@ class KeyType(enum.Enum):
             def maybe_read_from_path(key_path: Path) -> None:
                 try:
                     # as in parse.go in age:
-                    lines = Path(key_path).read_text().strip().splitlines()
+                    content = Path(key_path).read_text().strip()
-                    for private_key in filter(lambda ln: not ln.startswith("#"), lines):
+
-                        public_key = get_public_age_key(private_key)
+                    try:
+                        for public_key in get_public_age_keys(content):
                             log.info(
                                 f"Found age public key from a private key "
                                 f"in {key_path}: {public_key}"
                             )
+
                             keyring.append(public_key)
+                    except ClanError as e:
+                        error_msg = f"Failed to read age keys from {key_path}"
+                        raise ClanError(error_msg) from e
+
                 except FileNotFoundError:
                     return
                 except Exception as ex:
@@ -72,13 +81,19 @@ class KeyType(enum.Enum):
                 # SOPS_AGE_KEY is fed into age.ParseIdentities by Sops, and
                 # reads identities line by line. See age/keysource.go in
                 # Sops, and age/parse.go in Age.
-                for private_key in keys.strip().splitlines():
+                content = keys.strip()
-                    public_key = get_public_age_key(private_key)
+
+                try:
+                    for public_key in get_public_age_keys(content):
                         log.info(
                             f"Found age public key from a private key "
                             f"in the environment (SOPS_AGE_KEY): {public_key}"
                         )
+
                         keyring.append(public_key)
+                except ClanError as e:
+                    error_msg = "Failed to read age keys from SOPS_AGE_KEY"
+                    raise ClanError(error_msg) from e
 
             # Sops will try every location, see age/keysource.go
             elif key_path := os.environ.get("SOPS_AGE_KEY_FILE"):
@@ -176,7 +191,41 @@ class Operation(enum.StrEnum):
     UPDATE_KEYS = "updatekeys"
 
 
+def load_age_plugins(flake_dir: str | Path) -> list[str]:
+    if not flake_dir:
+        msg = "Missing flake directory"
+        raise ClanError(msg)
+
+    cmd = nix_eval(
+        [
+            f"{flake_dir}#clanInternals.secrets.age.plugins",
+            "--json",
+        ]
+    )
+
+    try:
+        result = run(cmd)
+    except Exception as e:
+        msg = f"Failed to load age plugins {flake_dir}"
+        raise ClanError(msg) from e
+
+    json_str = result.stdout.strip()
+
+    try:
+        plugins = json.loads(json_str)
+    except json.JSONDecodeError as e:
+        msg = f"Failed to decode '{json_str}': {e}"
+        raise ClanError(msg) from e
+
+    if isinstance(plugins, list):
+        return plugins
+
+    msg = f"Expected a list of age plugins but {type(plugins)!r} was provided"
+    raise ClanError(msg)
+
+
 def sops_run(
+    flake_dir: str | Path,
     call: Operation,
     secret_path: Path,
     public_keys: Iterable[SopsKey],
@@ -234,7 +283,9 @@ def sops_run(
                 raise ClanError(msg)
         sops_cmd.append(str(secret_path))
 
-        cmd = nix_shell(["sops", "gnupg"], sops_cmd)
+        age_plugins = load_age_plugins(flake_dir)
+
+        cmd = nix_shell(["sops", "gnupg", *age_plugins], sops_cmd)
         opts = (
             dataclasses.replace(run_opts, env=environ)
             if run_opts
@@ -249,7 +300,44 @@ def sops_run(
         return p.returncode, p.stdout
 
 
-def get_public_age_key(privkey: str) -> str:
+def get_public_age_keys(contents: str) -> set[str]:
+    # we use a set as it's possible we may detect the same key twice, once in a `# comment` and once by recovering it
+    # from AGE-SECRET-KEY
+    keys: set[str] = set()
+    recipient: str | None = None
+
+    for line_number, line in enumerate(contents.splitlines()):
+        match = AGE_RECIPIENT_REGEX.match(line)
+
+        if match:
+            recipient = match[1]
+            keys.add(recipient)
+
+        if line.startswith("#"):
+            continue
+
+        if line.startswith("AGE-PLUGIN-"):
+            if not recipient:
+                msg = f"Did you forget to precede line {line_number} with it's corresponding `# recipient: age1xxxxxxxx` entry?"
+                raise ClanError(msg)
+
+            # reset recipient
+            recipient = None
+
+        if line.startswith("AGE-SECRET-KEY-"):
+            try:
+                keys.add(get_public_age_key_from_private_key(line))
+            except Exception as e:
+                msg = "Failed to get public key for age private key. Is the key malformed?"
+                raise ClanError(msg) from e
+
+            # reset recipient
+            recipient = None
+
+    return keys
+
+
+def get_public_age_key_from_private_key(privkey: str) -> str:
     cmd = nix_shell(["age"], ["age-keygen", "-y"])
 
     error_msg = "Failed to get public key for age private key. Is the key malformed?"
@@ -298,23 +386,7 @@ def get_user_name(flake_dir: Path, user: str) -> str:
         print(f"{flake_dir / user} already exists")
 
 
-def maybe_get_user_or_machine(flake_dir: Path, key: SopsKey) -> set[SopsKey] | None:
+def maybe_get_user(flake_dir: Path, key: SopsKey) -> set[SopsKey] | None:
-    folders = [sops_users_folder(flake_dir), sops_machines_folder(flake_dir)]
-
-    for folder in folders:
-        if folder.exists():
-            for user in folder.iterdir():
-                if not (user / "key.json").exists():
-                    continue
-
-                keys = read_keys(user)
-                if key in keys:
-                    return {SopsKey(key.pubkey, user.name, key.key_type)}
-
-    return None
-
-
-def get_user(flake_dir: Path, key: SopsKey) -> set[SopsKey] | None:
     folder = sops_users_folder(flake_dir)
 
     if folder.exists():
@@ -324,20 +396,11 @@ def get_user(flake_dir: Path, key: SopsKey) -> set[SopsKey] | None:
 
             keys = read_keys(user)
             if key in keys:
-                return {SopsKey(key.pubkey, user.name, key.key_type)}
+                return {SopsKey(key.pubkey, user.name, key.key_type) for key in keys}
 
     return None
 
 
-@API.register
-def ensure_user_or_machine(flake_dir: Path, key: SopsKey) -> set[SopsKey]:
-    maybe_keys = maybe_get_user_or_machine(flake_dir, key)
-    if maybe_keys:
-        return maybe_keys
-    msg = f"A sops key is not yet added to the repository. Please add it with 'clan secrets users add youruser {key.pubkey}' (replace youruser with your user name)"
-    raise ClanError(msg)
-
-
 def default_admin_private_key_path() -> Path:
     raw_path = os.environ.get("SOPS_AGE_KEY_FILE")
     if raw_path:
@@ -346,8 +409,9 @@ def default_admin_private_key_path() -> Path:
 
 
 @API.register
-def maybe_get_admin_public_key() -> None | SopsKey:
+def maybe_get_admin_public_key() -> SopsKey | None:
     keyring = SopsKey.collect_public_keys()
+
     if len(keyring) == 0:
         return None
 
@@ -366,19 +430,31 @@ def maybe_get_admin_public_key() -> None | SopsKey:
     return keyring[0]
 
 
-def ensure_admin_public_key(flake_dir: Path) -> set[SopsKey]:
+def ensure_admin_public_keys(flake_dir: Path) -> set[SopsKey]:
     key = maybe_get_admin_public_key()
-    if key:
+
-        return ensure_user_or_machine(flake_dir, key)
+    if not key:
-    msg = "No sops key found. Please generate one with 'clan secrets key generate'."
+        msg = "No SOPS key found. Please generate one with `clan secrets key generate`."
         raise ClanError(msg)
 
+    user_keys = maybe_get_user(flake_dir, key)
 
-def update_keys(secret_path: Path, keys: Iterable[SopsKey]) -> list[Path]:
+    if not user_keys:
+        # todo improve error message
+        msg = f"We could not figure out which Clan secrets user you are with the SOPS key we found: {key.pubkey}"
+        raise ClanError(msg)
+
+    return user_keys
+
+
+def update_keys(
+    flake_dir: str | Path, secret_path: Path, keys: Iterable[SopsKey]
+) -> list[Path]:
     secret_path = secret_path / "secret"
     error_msg = f"Could not update keys for {secret_path}"
 
     rc, _ = sops_run(
+        flake_dir,
         Operation.UPDATE_KEYS,
         secret_path,
         keys,
@@ -389,6 +465,7 @@ def update_keys(secret_path: Path, keys: Iterable[SopsKey]) -> list[Path]:
 
 
 def encrypt_file(
+    flake_dir: str | Path,
     secret_path: Path,
     content: str | IO[bytes] | bytes | None,
     pubkeys: list[SopsKey],
@@ -399,6 +476,7 @@ def encrypt_file(
     if not content:
         # This will spawn an editor to edit the file.
         rc, _ = sops_run(
+            flake_dir,
             Operation.EDIT,
             secret_path,
             pubkeys,
@@ -437,6 +515,7 @@ def encrypt_file(
                 msg = f"Invalid content type: {type(content)}"
                 raise ClanError(msg)
         sops_run(
+            flake_dir,
             Operation.ENCRYPT,
             Path(source.name),
             pubkeys,
@@ -451,11 +530,12 @@ def encrypt_file(
             Path(source.name).unlink()
 
 
-def decrypt_file(secret_path: Path) -> str:
+def decrypt_file(flake_dir: str | Path, secret_path: Path) -> str:
     # decryption uses private keys from the environment or default paths:
     no_public_keys_needed: list[SopsKey] = []
 
     _, stdout = sops_run(
+        flake_dir,
         Operation.DECRYPT,
         secret_path,
         no_public_keys_needed,

pkgs/clan-cli/clan_cli/secrets/types.py

@@ -5,7 +5,7 @@ from pathlib import Path
 
 from clan_cli.errors import ClanError
 
-from .sops import get_public_age_key
+from .sops import get_public_age_keys
 
 VALID_SECRET_NAME = re.compile(r"^[a-zA-Z0-9._-]+$")
 VALID_USER_NAME = re.compile(r"^[a-z_]([a-z0-9_-]{0,31})?$")
@@ -21,14 +21,19 @@ def secret_name_type(arg_value: str) -> str:
 def public_or_private_age_key_type(arg_value: str) -> str:
     if Path(arg_value).is_file():
         arg_value = Path(arg_value).read_text().strip()
-    for line in arg_value.splitlines():
+
-        if line.startswith("#"):
+    public_keys = get_public_age_keys(arg_value)
-            continue
+
-        if line.startswith("age1"):
+    match len(public_keys):
-            return line.strip()
+        case 0:
-        if line.startswith("AGE-SECRET-KEY-"):
+            msg = f"Please provide an age public key starting with age1 or an age private key starting with AGE-SECRET-KEY- or AGE-PLUGIN-, got: '{arg_value}'"
-            return get_public_age_key(line)
+            raise ClanError(msg)
-    msg = f"Please provide an age public key starting with age1 or an age private key AGE-SECRET-KEY-, got: '{arg_value}'"
+
+        case 1:
+            return next(iter(public_keys))
+
+        case n:
+            msg = f"{n} age keys were provided, please provide only 1: '{arg_value}'"
             raise ClanError(msg)
 
 

pkgs/clan-cli/clan_cli/secrets/users.py

@@ -93,6 +93,7 @@ def list_users(flake_dir: Path) -> list[str]:
 
 def add_secret(flake_dir: Path, user: str, secret: str) -> None:
     updated_paths = secrets.allow_member(
+        flake_dir,
         secrets.users_folder(sops_secrets_folder(flake_dir) / secret),
         sops_users_folder(flake_dir),
         user,
@@ -106,7 +107,7 @@ def add_secret(flake_dir: Path, user: str, secret: str) -> None:
 
 def remove_secret(flake_dir: Path, user: str, secret: str) -> None:
     updated_paths = secrets.disallow_member(
-        secrets.users_folder(sops_secrets_folder(flake_dir) / secret), user
+        flake_dir, secrets.users_folder(sops_secrets_folder(flake_dir) / secret), user
     )
     commit_files(
         updated_paths,

pkgs/clan-cli/clan_cli/tests/age_keys.py

@@ -62,6 +62,10 @@ KEYS = [
         "age1eyyhln9g3cdwtrwpckugvqgtf5p8ugt0426sw38ra3wkc0t4rfhslq7txv",
         "AGE-SECRET-KEY-1567QKA63Y9P62SHF5TCHVCT5GZX2LZ8NS0E9RKA2QHDA662SF5LQ2VJJYX",
     ),
+    KeyPair(
+        "age1e9ufa6wrsr5danka50qp0np0832uz7jca7s00wyeg2nt3aqnvaks7p4jfr",
+        "AGE-SECRET-KEY-1Z89SHU9KAF709TTAZDARUWKC7H9TPZW4L8A2PVYSYAF7QVLCNQZQZ07U5J",
+    ),
 ]
 
 

pkgs/clan-cli/clan_cli/tests/test_import_sops_cli.py

@@ -10,9 +10,10 @@ if TYPE_CHECKING:
     from .age_keys import KeyPair
 
 
+@pytest.mark.with_core
 def test_import_sops(
     test_root: Path,
-    test_flake: FlakeForTest,
+    test_flake_with_core: FlakeForTest,
     capture_output: CaptureOutput,
     monkeypatch: pytest.MonkeyPatch,
     age_keys: list["KeyPair"],
@@ -24,7 +25,7 @@ def test_import_sops(
             "machines",
             "add",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "machine1",
             age_keys[0].pubkey,
         ]
@@ -35,7 +36,7 @@ def test_import_sops(
             "users",
             "add",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "user1",
             age_keys[1].pubkey,
         ]
@@ -46,7 +47,7 @@ def test_import_sops(
             "users",
             "add",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "user2",
             age_keys[2].pubkey,
         ]
@@ -57,7 +58,7 @@ def test_import_sops(
             "groups",
             "add-user",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "group1",
             "user1",
         ]
@@ -68,7 +69,7 @@ def test_import_sops(
             "groups",
             "add-user",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "group1",
             "user2",
         ]
@@ -80,7 +81,7 @@ def test_import_sops(
         "secrets",
         "import-sops",
         "--flake",
-        str(test_flake.path),
+        str(test_flake_with_core.path),
         "--group",
         "group1",
         "--machine",
@@ -90,10 +91,13 @@ def test_import_sops(
 
     cli.run(cmd)
     with capture_output as output:
-        cli.run(["secrets", "users", "list", "--flake", str(test_flake.path)])
+        cli.run(["secrets", "users", "list", "--flake", str(test_flake_with_core.path)])
+
     users = sorted(output.out.rstrip().split())
     assert users == ["user1", "user2"]
 
     with capture_output as output:
-        cli.run(["secrets", "get", "--flake", str(test_flake.path), "secret-key"])
+        cli.run(
+            ["secrets", "get", "--flake", str(test_flake_with_core.path), "secret-key"]
+        )
     assert output.out == "secret-value"

pkgs/clan-cli/clan_cli/tests/test_modules.py

@@ -40,6 +40,8 @@ def test_add_module_to_inventory(
     age_keys: list["KeyPair"],
 ) -> None:
     base_path = test_flake_with_core.path
+
+    with monkeypatch.context():
         monkeypatch.chdir(test_flake_with_core.path)
         monkeypatch.setenv("SOPS_AGE_KEY", age_keys[0].privkey)
 
@@ -60,7 +62,9 @@ def test_add_module_to_inventory(
         )
 
         create_machine(opts)
-    (test_flake_with_core.path / "machines" / "machine1" / "facter.json").write_text(
+        (
+            test_flake_with_core.path / "machines" / "machine1" / "facter.json"
+        ).write_text(
             json.dumps(
                 {
                     "version": 1,
@@ -87,7 +91,13 @@ def test_add_module_to_inventory(
         set_inventory(inventory, base_path, "Add borgbackup service")
 
         # cmd = ["facts", "generate", "--flake", str(test_flake_with_core.path), "machine1"]
-    cmd = ["vars", "generate", "--flake", str(test_flake_with_core.path), "machine1"]
+        cmd = [
+            "vars",
+            "generate",
+            "--flake",
+            str(test_flake_with_core.path),
+            "machine1",
+        ]
 
         cli.run(cmd)
 

pkgs/clan-cli/clan_cli/tests/test_secrets_cli.py

@@ -1,7 +1,9 @@
 import json
 import logging
 import os
+import random
 import re
+import string
 from collections.abc import Iterator
 from contextlib import contextmanager
 from typing import TYPE_CHECKING
@@ -20,14 +22,15 @@ if TYPE_CHECKING:
 log = logging.getLogger(__name__)
 
 
+@pytest.mark.with_core
 def _test_identities(
     what: str,
-    test_flake: FlakeForTest,
+    test_flake_with_core: FlakeForTest,
     capture_output: CaptureOutput,
     age_keys: list["KeyPair"],
     monkeypatch: pytest.MonkeyPatch,
 ) -> None:
-    sops_folder = test_flake.path / "sops"
+    sops_folder = test_flake_with_core.path / "sops"
 
     what_singular = what[:-1]
     test_secret_name = f"{what_singular}_secret"
@@ -43,7 +46,7 @@ def _test_identities(
             what,
             "add",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "foo",
             age_keys[0].pubkey,
         ]
@@ -56,7 +59,7 @@ def _test_identities(
             "users",
             "add",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "admin",
             admin_age_key.pubkey,
         ]
@@ -69,28 +72,30 @@ def _test_identities(
                 what,
                 "add",
                 "--flake",
-                str(test_flake.path),
+                str(test_flake_with_core.path),
                 "foo",
                 age_keys[0].pubkey,
             ]
         )
 
-    with monkeypatch.context():
+    with monkeypatch.context() as m:
-        monkeypatch.setenv("SOPS_NIX_SECRET", "deadfeed")
+        m.setenv("SOPS_NIX_SECRET", "deadfeed")
-        monkeypatch.setenv("SOPS_AGE_KEY", admin_age_key.privkey)
+        m.setenv("SOPS_AGE_KEY", admin_age_key.privkey)
+
         cli.run(
             [
                 "secrets",
                 "set",
                 "--flake",
-                str(test_flake.path),
+                str(test_flake_with_core.path),
                 f"--{what_singular}",
                 "foo",
                 test_secret_name,
             ]
         )
+
     assert_secrets_file_recipients(
-        test_flake.path,
+        test_flake_with_core.path,
         test_secret_name,
         expected_age_recipients_keypairs=[age_keys[0], admin_age_key],
     )
@@ -103,14 +108,14 @@ def _test_identities(
                 what,
                 "add",
                 "--flake",
-                str(test_flake.path),
+                str(test_flake_with_core.path),
                 "-f",
                 "foo",
                 age_keys[1].privkey,
             ]
         )
     assert_secrets_file_recipients(
-        test_flake.path,
+        test_flake_with_core.path,
         test_secret_name,
         expected_age_recipients_keypairs=[age_keys[1], admin_age_key],
     )
@@ -122,24 +127,35 @@ def _test_identities(
                 what,
                 "get",
                 "--flake",
-                str(test_flake.path),
+                str(test_flake_with_core.path),
                 "foo",
             ]
         )
     assert age_keys[1].pubkey in output.out
 
     with capture_output as output:
-        cli.run(["secrets", what, "list", "--flake", str(test_flake.path)])
+        cli.run(["secrets", what, "list", "--flake", str(test_flake_with_core.path)])
     assert "foo" in output.out
 
-    cli.run(["secrets", what, "remove", "--flake", str(test_flake.path), "foo"])
+    cli.run(
+        ["secrets", what, "remove", "--flake", str(test_flake_with_core.path), "foo"]
+    )
     assert not (sops_folder / what / "foo" / "key.json").exists()
 
     with pytest.raises(ClanError):  # already removed
-        cli.run(["secrets", what, "remove", "--flake", str(test_flake.path), "foo"])
+        cli.run(
+            [
+                "secrets",
+                what,
+                "remove",
+                "--flake",
+                str(test_flake_with_core.path),
+                "foo",
+            ]
+        )
 
     with capture_output as output:
-        cli.run(["secrets", what, "list", "--flake", str(test_flake.path)])
+        cli.run(["secrets", what, "list", "--flake", str(test_flake_with_core.path)])
     assert "foo" not in output.out
 
     user_or_machine_symlink = sops_folder / "secrets" / test_secret_name / what / "foo"
@@ -151,112 +167,186 @@ def _test_identities(
     assert not user_or_machine_symlink.exists(follow_symlinks=False), err_msg
 
 
+@pytest.mark.with_core
 def test_users(
-    test_flake: FlakeForTest,
+    test_flake_with_core: FlakeForTest,
     capture_output: CaptureOutput,
     age_keys: list["KeyPair"],
     monkeypatch: pytest.MonkeyPatch,
 ) -> None:
-    _test_identities("users", test_flake, capture_output, age_keys, monkeypatch)
+    with monkeypatch.context():
+        _test_identities(
+            "users", test_flake_with_core, capture_output, age_keys, monkeypatch
+        )
 
-    # some additional user-specific tests
 
-    admin_key = age_keys[2]
+@pytest.mark.with_core
-    sops_folder = test_flake.path / "sops"
+def test_multiple_user_keys(
+    test_flake_with_core: FlakeForTest,
+    capture_output: CaptureOutput,
+    age_keys: list["KeyPair"],
+    monkeypatch: pytest.MonkeyPatch,
+) -> None:
+    sops_folder = test_flake_with_core.path / "sops"
 
-    user_keys = {
+    users_keys = {
-        "bob": [age_keys[0], age_keys[1]],
+        "bob": {age_keys[0], age_keys[1]},
-        "alice": [age_keys[2]],
+        "alice": {age_keys[2]},
-        "charlie": [age_keys[3], age_keys[4]],
+        "charlie": {age_keys[3], age_keys[4], age_keys[5]},
     }
 
-    for user, keys in user_keys.items():
+    for user, user_keys in users_keys.items():
-        key_args = [f"--age-key={key.pubkey}" for key in keys]
+        # add the user
-
-        # add the user keys
         cli.run(
             [
                 "secrets",
                 "users",
                 "add",
                 "--flake",
-                str(test_flake.path),
+                str(test_flake_with_core.path),
                 user,
-                *key_args,
+                *[f"--age-key={key.pubkey}" for key in user_keys],
             ]
         )
         assert (sops_folder / "users" / user / "key.json").exists()
 
         # check they are returned in get
         with capture_output as output:
-            cli.run(["secrets", "users", "get", "--flake", str(test_flake.path), user])
+            cli.run(
+                [
+                    "secrets",
+                    "users",
+                    "get",
+                    "--flake",
+                    str(test_flake_with_core.path),
+                    user,
+                ]
+            )
 
-        for key in keys:
+        for user_key in user_keys:
-            assert key.pubkey in output.out
+            assert user_key.pubkey in output.out
+
+        # let's do some setting and getting of secrets
+
+        def random_str() -> str:
+            return "".join(random.choices(string.ascii_letters, k=10))
+
+        for user_key in user_keys:
+            # set a secret using each of the user's private keys
+            with monkeypatch.context():
+                secret_name = f"{user}_secret_{random_str()}"
+                secret_value = random_str()
+
+                monkeypatch.setenv("SOPS_AGE_KEY", user_key.privkey)
+                monkeypatch.setenv("SOPS_NIX_SECRET", secret_value)
 
-        # set a secret
-        secret_name = f"{user}_secret"
                 cli.run(
                     [
                         "secrets",
                         "set",
                         "--flake",
-                str(test_flake.path),
+                        str(test_flake_with_core.path),
-                "--user",
-                user,
                         secret_name,
                     ]
                 )
 
                 # check the secret has each of our user's keys as a recipient
-        # in addition the admin key should be there
                 assert_secrets_file_recipients(
-            test_flake.path,
+                    test_flake_with_core.path,
                     secret_name,
-            expected_age_recipients_keypairs=[admin_key, *keys],
+                    expected_age_recipients_keypairs=[*user_keys],
                 )
 
-        if len(keys) == 1:
+                # check we can get the secret
+                with capture_output as output:
+                    cli.run(
+                        [
+                            "secrets",
+                            "get",
+                            "--flake",
+                            str(test_flake_with_core.path),
+                            secret_name,
+                        ]
+                    )
+
+                assert secret_value in output.out
+
+        if len(user_keys) == 1:
             continue
 
-        # remove one of the keys
+        # remove one of the user keys,
+        user_keys_iter = iter(user_keys)
+
+        key_to_remove = next(user_keys_iter)
+        key_to_encrypt_with = next(user_keys_iter)
+
+        with monkeypatch.context():
+            monkeypatch.setenv("SOPS_AGE_KEY", key_to_encrypt_with.privkey)
+            monkeypatch.setenv("SOPS_NIX_SECRET", "deafbeef")
+
             cli.run(
                 [
                     "secrets",
                     "users",
                     "remove-key",
                     "--flake",
-                str(test_flake.path),
+                    str(test_flake_with_core.path),
                     user,
-                keys[0].pubkey,
+                    key_to_remove.pubkey,
                 ]
             )
 
             # check the secret has been updated
             assert_secrets_file_recipients(
-            test_flake.path,
+                test_flake_with_core.path,
                 secret_name,
-            expected_age_recipients_keypairs=[admin_key, *keys[1:]],
+                expected_age_recipients_keypairs=list({*user_keys} - {key_to_remove}),
+            )
+
+            # add the key back
+            cli.run(
+                [
+                    "secrets",
+                    "users",
+                    "add-key",
+                    "--flake",
+                    str(test_flake_with_core.path),
+                    user,
+                    key_to_remove.pubkey,
+                ]
+            )
+
+            # check the secret has been updated
+            assert_secrets_file_recipients(
+                test_flake_with_core.path,
+                secret_name,
+                expected_age_recipients_keypairs=user_keys,
             )
 
 
+@pytest.mark.with_core
 def test_machines(
-    test_flake: FlakeForTest,
+    test_flake_with_core: FlakeForTest,
     capture_output: CaptureOutput,
     age_keys: list["KeyPair"],
     monkeypatch: pytest.MonkeyPatch,
 ) -> None:
-    _test_identities("machines", test_flake, capture_output, age_keys, monkeypatch)
+    _test_identities(
+        "machines", test_flake_with_core, capture_output, age_keys, monkeypatch
+    )
 
 
+@pytest.mark.with_core
 def test_groups(
-    test_flake: FlakeForTest,
+    test_flake_with_core: FlakeForTest,
     capture_output: CaptureOutput,
     age_keys: list["KeyPair"],
     monkeypatch: pytest.MonkeyPatch,
 ) -> None:
     with capture_output as output:
-        cli.run(["secrets", "groups", "list", "--flake", str(test_flake.path)])
+        cli.run(
+            ["secrets", "groups", "list", "--flake", str(test_flake_with_core.path)]
+        )
     assert output.out == ""
 
     machine1_age_key = age_keys[0]
@@ -270,7 +360,7 @@ def test_groups(
                 "groups",
                 "add-machine",
                 "--flake",
-                str(test_flake.path),
+                str(test_flake_with_core.path),
                 "group1",
                 "machine1",
             ]
@@ -282,7 +372,7 @@ def test_groups(
                 "groups",
                 "add-user",
                 "--flake",
-                str(test_flake.path),
+                str(test_flake_with_core.path),
                 "groupb1",
                 "user1",
             ]
@@ -293,7 +383,7 @@ def test_groups(
             "machines",
             "add",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "machine1",
             machine1_age_key.pubkey,
         ]
@@ -304,7 +394,7 @@ def test_groups(
             "groups",
             "add-machine",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "group1",
             "machine1",
         ]
@@ -317,7 +407,7 @@ def test_groups(
             "groups",
             "add-machine",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "group1",
             "machine1",
         ]
@@ -329,7 +419,7 @@ def test_groups(
             "users",
             "add",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "user1",
             user1_age_key.pubkey,
         ]
@@ -340,7 +430,7 @@ def test_groups(
             "users",
             "add",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "admin",
             admin_age_key.pubkey,
         ]
@@ -351,14 +441,16 @@ def test_groups(
             "groups",
             "add-user",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "group1",
             "user1",
         ]
     )
 
     with capture_output as output:
-        cli.run(["secrets", "groups", "list", "--flake", str(test_flake.path)])
+        cli.run(
+            ["secrets", "groups", "list", "--flake", str(test_flake_with_core.path)]
+        )
     out = output.out
     assert "user1" in out
     assert "machine1" in out
@@ -368,12 +460,13 @@ def test_groups(
     with monkeypatch.context():
         monkeypatch.setenv("SOPS_NIX_SECRET", "deafbeef")
         monkeypatch.setenv("SOPS_AGE_KEY", admin_age_key.privkey)
+
         cli.run(
             [
                 "secrets",
                 "set",
                 "--flake",
-                str(test_flake.path),
+                str(test_flake_with_core.path),
                 "--group",
                 "group1",
                 secret_name,
@@ -381,7 +474,7 @@ def test_groups(
         )
 
     assert_secrets_file_recipients(
-        test_flake.path,
+        test_flake_with_core.path,
         secret_name,
         expected_age_recipients_keypairs=[
             machine1_age_key,
@@ -400,13 +493,13 @@ def test_groups(
             "groups",
             "remove-user",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "group1",
             "user1",
         ]
     )
     assert_secrets_file_recipients(
-        test_flake.path,
+        test_flake_with_core.path,
         secret_name,
         expected_age_recipients_keypairs=[machine1_age_key, admin_age_key],
         err_msg=(
@@ -422,13 +515,13 @@ def test_groups(
             "groups",
             "add-user",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "group1",
             "user1",
         ]
     )
     assert_secrets_file_recipients(
-        test_flake.path,
+        test_flake_with_core.path,
         secret_name,
         expected_age_recipients_keypairs=[
             machine1_age_key,
@@ -444,12 +537,12 @@ def test_groups(
             "users",
             "remove",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "user1",
         ]
     )
     assert_secrets_file_recipients(
-        test_flake.path,
+        test_flake_with_core.path,
         secret_name,
         expected_age_recipients_keypairs=[machine1_age_key, admin_age_key],
         err_msg=(
@@ -464,13 +557,13 @@ def test_groups(
             "groups",
             "remove-machine",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "group1",
             "machine1",
         ]
     )
     assert_secrets_file_recipients(
-        test_flake.path,
+        test_flake_with_core.path,
         secret_name,
         expected_age_recipients_keypairs=[admin_age_key],
         err_msg=(
@@ -479,11 +572,11 @@ def test_groups(
         ),
     )
 
-    first_group = next((test_flake.path / "sops" / "groups").iterdir(), None)
+    first_group = next((test_flake_with_core.path / "sops" / "groups").iterdir(), None)
     assert first_group is None
 
     # Check if the symlink to the group was removed from our foo test secret:
-    group_symlink = test_flake.path / "sops/secrets/foo/groups/group1"
+    group_symlink = test_flake_with_core.path / "sops/secrets/foo/groups/group1"
     err_msg = (
         "Symlink to group1's key in foo secret "
         "was not cleaned up after group1 was removed"
@@ -520,61 +613,105 @@ def use_gpg_key(key: GpgKey, monkeypatch: pytest.MonkeyPatch) -> Iterator[None]:
             monkeypatch.setenv("SOPS_AGE_KEY", old_key)
 
 
+@pytest.mark.with_core
 def test_secrets(
-    test_flake: FlakeForTest,
+    test_flake_with_core: FlakeForTest,
     capture_output: CaptureOutput,
     monkeypatch: pytest.MonkeyPatch,
     gpg_key: GpgKey,
     age_keys: list["KeyPair"],
 ) -> None:
     with capture_output as output:
-        cli.run(["secrets", "list", "--flake", str(test_flake.path)])
+        cli.run(["secrets", "list", "--flake", str(test_flake_with_core.path)])
     assert output.out == ""
 
     # Generate a new key for the clan
-    monkeypatch.setenv("SOPS_AGE_KEY_FILE", str(test_flake.path / ".." / "age.key"))
+    monkeypatch.setenv(
+        "SOPS_AGE_KEY_FILE", str(test_flake_with_core.path / ".." / "age.key")
+    )
     with capture_output as output:
-        cli.run(["secrets", "key", "generate", "--flake", str(test_flake.path)])
+        cli.run(
+            ["secrets", "key", "generate", "--flake", str(test_flake_with_core.path)]
+        )
     assert "age private key" in output.out
     # Read the key that was generated
     with capture_output as output:
-        cli.run(["secrets", "key", "show", "--flake", str(test_flake.path)])
+        cli.run(["secrets", "key", "show", "--flake", str(test_flake_with_core.path)])
-    key = json.loads(output.out)["publickey"]
+
-    assert key.startswith("age1")
+    key = json.loads(output.out)
+    assert key["publickey"].startswith("age1")
     # Add testuser with the key that was generated for the clan
     cli.run(
-        ["secrets", "users", "add", "--flake", str(test_flake.path), "testuser", key]
+        [
+            "secrets",
+            "users",
+            "add",
+            "--flake",
+            str(test_flake_with_core.path),
+            "testuser",
+            key["publickey"],
+        ]
     )
 
     with pytest.raises(ClanError):  # does not exist yet
-        cli.run(["secrets", "get", "--flake", str(test_flake.path), "nonexisting"])
+        cli.run(
+            ["secrets", "get", "--flake", str(test_flake_with_core.path), "nonexisting"]
+        )
     monkeypatch.setenv("SOPS_NIX_SECRET", "foo")
-    cli.run(["secrets", "set", "--flake", str(test_flake.path), "initialkey"])
+    cli.run(["secrets", "set", "--flake", str(test_flake_with_core.path), "initialkey"])
     with capture_output as output:
-        cli.run(["secrets", "get", "--flake", str(test_flake.path), "initialkey"])
+        cli.run(
+            ["secrets", "get", "--flake", str(test_flake_with_core.path), "initialkey"]
+        )
     assert output.out == "foo"
     with capture_output as output:
-        cli.run(["secrets", "users", "list", "--flake", str(test_flake.path)])
+        cli.run(["secrets", "users", "list", "--flake", str(test_flake_with_core.path)])
     users = output.out.rstrip().split("\n")
     assert len(users) == 1, f"users: {users}"
     owner = users[0]
 
     monkeypatch.setenv("EDITOR", "cat")
-    cli.run(["secrets", "set", "--edit", "--flake", str(test_flake.path), "initialkey"])
+    cli.run(
+        [
+            "secrets",
+            "set",
+            "--edit",
+            "--flake",
+            str(test_flake_with_core.path),
+            "initialkey",
+        ]
+    )
     monkeypatch.delenv("EDITOR")
 
-    cli.run(["secrets", "rename", "--flake", str(test_flake.path), "initialkey", "key"])
+    cli.run(
+        [
+            "secrets",
+            "rename",
+            "--flake",
+            str(test_flake_with_core.path),
+            "initialkey",
+            "key",
+        ]
+    )
 
     with capture_output as output:
-        cli.run(["secrets", "list", "--flake", str(test_flake.path)])
+        cli.run(["secrets", "list", "--flake", str(test_flake_with_core.path)])
     assert output.out == "key\n"
 
     with capture_output as output:
-        cli.run(["secrets", "list", "--flake", str(test_flake.path), "nonexisting"])
+        cli.run(
+            [
+                "secrets",
+                "list",
+                "--flake",
+                str(test_flake_with_core.path),
+                "nonexisting",
+            ]
+        )
     assert output.out == ""
 
     with capture_output as output:
-        cli.run(["secrets", "list", "--flake", str(test_flake.path), "key"])
+        cli.run(["secrets", "list", "--flake", str(test_flake_with_core.path), "key"])
     assert output.out == "key\n"
 
     # using the `age_keys` KeyPair, add a machine and rotate its key
@@ -585,7 +722,7 @@ def test_secrets(
             "machines",
             "add",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "machine1",
             age_keys[1].pubkey,
         ]
@@ -596,18 +733,22 @@ def test_secrets(
             "machines",
             "add-secret",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "machine1",
             "key",
         ]
     )
     with capture_output as output:
-        cli.run(["secrets", "machines", "list", "--flake", str(test_flake.path)])
+        cli.run(
+            ["secrets", "machines", "list", "--flake", str(test_flake_with_core.path)]
+        )
     assert output.out == "machine1\n"
 
     with use_age_key(age_keys[1].privkey, monkeypatch):
         with capture_output as output:
-            cli.run(["secrets", "get", "--flake", str(test_flake.path), "key"])
+            cli.run(
+                ["secrets", "get", "--flake", str(test_flake_with_core.path), "key"]
+            )
         assert output.out == "foo"
 
     # rotate machines key
@@ -617,7 +758,7 @@ def test_secrets(
             "machines",
             "add",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "-f",
             "machine1",
             age_keys[0].privkey,
@@ -627,7 +768,9 @@ def test_secrets(
     # should also rotate the encrypted secret
     with use_age_key(age_keys[0].privkey, monkeypatch):
         with capture_output as output:
-            cli.run(["secrets", "get", "--flake", str(test_flake.path), "key"])
+            cli.run(
+                ["secrets", "get", "--flake", str(test_flake_with_core.path), "key"]
+            )
         assert output.out == "foo"
 
     cli.run(
@@ -636,7 +779,7 @@ def test_secrets(
             "machines",
             "remove-secret",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "machine1",
             "key",
         ]
@@ -648,7 +791,7 @@ def test_secrets(
             "users",
             "add",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "user1",
             age_keys[1].pubkey,
         ]
@@ -659,13 +802,13 @@ def test_secrets(
             "users",
             "add-secret",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "user1",
             "key",
         ]
     )
     with capture_output as output, use_age_key(age_keys[1].privkey, monkeypatch):
-        cli.run(["secrets", "get", "--flake", str(test_flake.path), "key"])
+        cli.run(["secrets", "get", "--flake", str(test_flake_with_core.path), "key"])
     assert output.out == "foo"
     cli.run(
         [
@@ -673,7 +816,7 @@ def test_secrets(
             "users",
             "remove-secret",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "user1",
             "key",
         ]
@@ -686,7 +829,7 @@ def test_secrets(
                 "groups",
                 "add-secret",
                 "--flake",
-                str(test_flake.path),
+                str(test_flake_with_core.path),
                 "admin-group",
                 "key",
             ]
@@ -697,7 +840,7 @@ def test_secrets(
             "groups",
             "add-user",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "admin-group",
             "user1",
         ]
@@ -708,7 +851,7 @@ def test_secrets(
             "groups",
             "add-user",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "admin-group",
             owner,
         ]
@@ -719,7 +862,7 @@ def test_secrets(
             "groups",
             "add-secret",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "admin-group",
             "key",
         ]
@@ -730,7 +873,7 @@ def test_secrets(
             "secrets",
             "set",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "--group",
             "admin-group",
             "key2",
@@ -739,7 +882,9 @@ def test_secrets(
 
     with use_age_key(age_keys[1].privkey, monkeypatch):
         with capture_output as output:
-            cli.run(["secrets", "get", "--flake", str(test_flake.path), "key"])
+            cli.run(
+                ["secrets", "get", "--flake", str(test_flake_with_core.path), "key"]
+            )
         assert output.out == "foo"
 
     # Add an user with a GPG key
@@ -749,7 +894,7 @@ def test_secrets(
             "users",
             "add",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "--pgp-key",
             gpg_key.fingerprint,
             "user2",
@@ -763,7 +908,7 @@ def test_secrets(
             "groups",
             "add-user",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "admin-group",
             "user2",
         ]
@@ -771,7 +916,9 @@ def test_secrets(
 
     with use_gpg_key(gpg_key, monkeypatch):  # user2
         with capture_output as output:
-            cli.run(["secrets", "get", "--flake", str(test_flake.path), "key"])
+            cli.run(
+                ["secrets", "get", "--flake", str(test_flake_with_core.path), "key"]
+            )
         assert output.out == "foo"
 
     cli.run(
@@ -780,7 +927,7 @@ def test_secrets(
             "groups",
             "remove-user",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "admin-group",
             "user2",
         ]
@@ -791,7 +938,7 @@ def test_secrets(
         capture_output as output,
     ):
         # user2 is not in the group anymore
-        cli.run(["secrets", "get", "--flake", str(test_flake.path), "key"])
+        cli.run(["secrets", "get", "--flake", str(test_flake_with_core.path), "key"])
     print(output.out)
 
     cli.run(
@@ -800,22 +947,23 @@ def test_secrets(
             "groups",
             "remove-secret",
             "--flake",
-            str(test_flake.path),
+            str(test_flake_with_core.path),
             "admin-group",
             "key",
         ]
     )
 
-    cli.run(["secrets", "remove", "--flake", str(test_flake.path), "key"])
+    cli.run(["secrets", "remove", "--flake", str(test_flake_with_core.path), "key"])
-    cli.run(["secrets", "remove", "--flake", str(test_flake.path), "key2"])
+    cli.run(["secrets", "remove", "--flake", str(test_flake_with_core.path), "key2"])
 
     with capture_output as output:
-        cli.run(["secrets", "list", "--flake", str(test_flake.path)])
+        cli.run(["secrets", "list", "--flake", str(test_flake_with_core.path)])
     assert output.out == ""
 
 
+@pytest.mark.with_core
 def test_secrets_key_generate_gpg(
-    test_flake: FlakeForTest,
+    test_flake_with_core: FlakeForTest,
     capture_output: CaptureOutput,
     monkeypatch: pytest.MonkeyPatch,
     gpg_key: GpgKey,
@@ -830,14 +978,16 @@ def test_secrets_key_generate_gpg(
                     "key",
                     "generate",
                     "--flake",
-                    str(test_flake.path),
+                    str(test_flake_with_core.path),
                 ]
             )
         assert "age private key" not in output.out
         assert re.match(r"PGP key.+is already set", output.err) is not None
 
         with capture_output as output:
-            cli.run(["secrets", "key", "show", "--flake", str(test_flake.path)])
+            cli.run(
+                ["secrets", "key", "show", "--flake", str(test_flake_with_core.path)]
+            )
         key = json.loads(output.out)
         assert key["type"] == "pgp"
         assert key["publickey"] == gpg_key.fingerprint
@@ -849,12 +999,13 @@ def test_secrets_key_generate_gpg(
                 "users",
                 "add",
                 "--flake",
-                str(test_flake.path),
+                str(test_flake_with_core.path),
                 "--pgp-key",
                 gpg_key.fingerprint,
                 "testuser",
             ]
         )
+
         with capture_output as output:
             cli.run(
                 [
@@ -862,7 +1013,7 @@ def test_secrets_key_generate_gpg(
                     "users",
                     "get",
                     "--flake",
-                    str(test_flake.path),
+                    str(test_flake_with_core.path),
                     "testuser",
                 ]
             )
@@ -873,8 +1024,26 @@ def test_secrets_key_generate_gpg(
         assert key["type"] == "pgp"
         assert key["publickey"] == gpg_key.fingerprint
 
-        monkeypatch.setenv("SOPS_NIX_SECRET", "secret-value")
+        with monkeypatch.context() as m:
-        cli.run(["secrets", "set", "--flake", str(test_flake.path), "secret-name"])
+            m.setenv("SOPS_NIX_SECRET", "secret-value")
+
+            cli.run(
+                [
+                    "secrets",
+                    "set",
+                    "--flake",
+                    str(test_flake_with_core.path),
+                    "secret-name",
+                ]
+            )
             with capture_output as output:
-            cli.run(["secrets", "get", "--flake", str(test_flake.path), "secret-name"])
+                cli.run(
+                    [
+                        "secrets",
+                        "get",
+                        "--flake",
+                        str(test_flake_with_core.path),
+                        "secret-name",
+                    ]
+                )
             assert output.out == "secret-value"

pkgs/clan-cli/clan_cli/tests/test_secrets_upload.py

@@ -44,6 +44,8 @@ def test_secrets_upload(
     config["clan"]["networking"]["targetHost"] = addr
     config["clan"]["core"]["facts"]["secretUploadDirectory"] = str(flake.path / "facts")
     flake.refresh()
+
+    with monkeypatch.context():
         monkeypatch.chdir(str(flake.path))
         monkeypatch.setenv("SOPS_AGE_KEY", age_keys[0].privkey)
 
@@ -81,7 +83,10 @@ def test_secrets_upload(
                 age_keys[1].pubkey,
             ]
         )
-    monkeypatch.setenv("SOPS_NIX_SECRET", age_keys[0].privkey)
+
+        with monkeypatch.context() as m:
+            m.setenv("SOPS_NIX_SECRET", age_keys[0].privkey)
+
             cli.run(["secrets", "set", "--flake", str(flake.path), "vm1-age.key"])
 
             flake_path = flake.path.joinpath("flake.nix")

pkgs/clan-cli/clan_cli/tests/test_vms_cli.py

@@ -32,8 +32,10 @@ def test_run(
     test_flake_with_core: FlakeForTest,
     age_keys: list["KeyPair"],
 ) -> None:
+    with monkeypatch.context():
         monkeypatch.chdir(test_flake_with_core.path)
         monkeypatch.setenv("SOPS_AGE_KEY", age_keys[0].privkey)
+
         cli.run(
             [
                 "secrets",

pkgs/clan-cli/clan_cli/vars/secret_modules/sops.py

@@ -302,6 +302,7 @@ class SecretStore(StoreBase):
 
                 for group in self.machine.deployment["sops"]["defaultGroups"]:
                     allow_member(
+                        self.machine.flake_dir,
                         groups_folder(secret_path),
                         sops_groups_folder(self.machine.flake_dir),
                         group,
@@ -310,6 +311,7 @@ class SecretStore(StoreBase):
                     )
 
                 update_keys(
+                    self.machine.flake_dir,
                     secret_path,
                     collect_keys_for_path(secret_path),
                 )