diff --git a/milatools/cli/commands.py b/milatools/cli/commands.py
index c38b4e88..891d967d 100644
--- a/milatools/cli/commands.py
+++ b/milatools/cli/commands.py
@@ -31,28 +31,11 @@
 import rich.logging
 from typing_extensions import TypedDict
 
+from milatools.__version__ import __version__
 from milatools.cli import console
-from milatools.utils.local_v1 import LocalV1
-from milatools.utils.remote_v1 import RemoteV1, SlurmRemote
-from milatools.utils.remote_v2 import RemoteV2
-from milatools.utils.vscode_utils import (
-    get_code_command,
-    # install_local_vscode_extensions_on_remote,
-    sync_vscode_extensions,
-    sync_vscode_extensions_with_hostnames,
-)
-
-from ..__version__ import __version__
-from .init_command import (
-    print_welcome_message,
-    setup_keys_on_login_node,
-    setup_passwordless_ssh_access,
-    setup_ssh_config,
-    setup_vscode_settings,
-    setup_windows_ssh_config_from_wsl,
-)
-from .profile import ensure_program, setup_profile
-from .utils import (
+from milatools.cli.init import init
+from milatools.cli.profile import ensure_program, setup_profile
+from milatools.cli.utils import (
     CLUSTERS,
     Cluster,
     CommandNotFoundError,
@@ -69,6 +52,14 @@
     running_inside_WSL,
     with_control_file,
 )
+from milatools.utils.local_v1 import LocalV1
+from milatools.utils.remote_v1 import RemoteV1, SlurmRemote
+from milatools.utils.remote_v2 import RemoteV2
+from milatools.utils.vscode_utils import (
+    get_code_command,
+    sync_vscode_extensions,
+    sync_vscode_extensions_with_hostnames,
+)
 
 if typing.TYPE_CHECKING:
     from typing_extensions import Unpack
@@ -492,32 +483,6 @@ def intranet(search: Sequence[str]) -> None:
     webbrowser.open(url)
 
 
-def init():
-    """Set up your configuration and credentials."""
-
-    #############################
-    # Step 1: SSH Configuration #
-    #############################
-
-    print("Checking ssh config")
-
-    ssh_config = setup_ssh_config()
-
-    # if we're running on WSL, we actually just copy the id_rsa + id_rsa.pub and the
-    # ~/.ssh/config to the Windows ssh directory (taking care to remove the
-    # ControlMaster-related entries) so that the user doesn't need to install Python on
-    # the Windows side.
-    if running_inside_WSL():
-        setup_windows_ssh_config_from_wsl(linux_ssh_config=ssh_config)
-
-    success = setup_passwordless_ssh_access(ssh_config=ssh_config)
-    if not success:
-        exit()
-    setup_keys_on_login_node()
-    setup_vscode_settings()
-    print_welcome_message()
-
-
 def forward(
     remote: str,
     page: str | None,
diff --git a/milatools/cli/init_command.py b/milatools/cli/init.py
similarity index 78%
rename from milatools/cli/init_command.py
rename to milatools/cli/init.py
index c58ebcf5..8829a672 100644
--- a/milatools/cli/init_command.py
+++ b/milatools/cli/init.py
@@ -9,21 +9,24 @@
 import sys
 import warnings
 from logging import getLogger as get_logger
-from pathlib import Path
+from pathlib import Path, PosixPath
 from typing import Any
 
 import questionary as qn
 from invoke.exceptions import UnexpectedExit
-
-from milatools.utils.remote_v2 import SSH_CONFIG_FILE
-
-from ..utils.local_v1 import LocalV1, check_passwordless, display
-from ..utils.remote_v1 import RemoteV1
-from ..utils.vscode_utils import (
+from paramiko.config import SSHConfig as SSHConfigReader
+
+from milatools.cli import console
+from milatools.cli.utils import SSHConfig as SSHConfigWriter
+from milatools.cli.utils import T, running_inside_WSL, yn
+from milatools.utils.local_v1 import display
+from milatools.utils.local_v2 import LocalV2
+from milatools.utils.remote_v1 import RemoteV1
+from milatools.utils.remote_v2 import control_socket_is_running, get_controlpath_for
+from milatools.utils.vscode_utils import (
     get_expected_vscode_settings_json_path,
     vscode_installed,
 )
-from .utils import SSHConfig, T, running_inside_WSL, yn
 
 logger = get_logger(__name__)
 
@@ -68,8 +71,8 @@
         # NOTE: will not work with --gres prior to Slurm 22.05, because srun --overlap
         # cannot share gpus
         "ProxyCommand": (
-            'ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh '
-            'mila-cpu --mem=8G"'
+            "ssh mila "
+            '"/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh mila-cpu --mem=8G"'
         ),
         "RemoteCommand": (
             "/cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu"
@@ -112,9 +115,37 @@
 }
 
 
+def init():
+    """Set up your configuration and credentials."""
+
+    #############################
+    # Step 1: SSH Configuration #
+    #############################
+
+    print("Checking ssh config")
+    ssh_config_path = Path("~/.ssh/config").expanduser()
+
+    setup_ssh_config(ssh_config_path=ssh_config_path)
+
+    # if we're running on WSL, we actually just copy the id_rsa + id_rsa.pub and the
+    # ~/.ssh/config to the Windows ssh directory (taking care to remove the
+    # ControlMaster-related entries) so that the user doesn't need to install Python on
+    # the Windows side.
+    if running_inside_WSL():
+        assert isinstance(ssh_config_path, PosixPath)  # we're running in linux (WSL).
+        setup_windows_ssh_config_from_wsl(linux_ssh_config_path=ssh_config_path)
+
+    success = setup_passwordless_ssh_access(ssh_config_path)
+    if not success:
+        exit()
+    setup_keys_on_login_node()
+    setup_vscode_settings()
+    print_welcome_message()
+
+
 def setup_ssh_config(
     ssh_config_path: str | Path = "~/.ssh/config",
-) -> SSHConfig:
+) -> SSHConfigReader:
     """Interactively sets up some useful entries in the ~/.ssh/config file on the local
     machine.
 
@@ -134,14 +165,18 @@ def setup_ssh_config(
     """
 
     ssh_config_path = _setup_ssh_config_file(ssh_config_path)
-    ssh_config = SSHConfig(ssh_config_path)
+
+    ssh_config = SSHConfigReader.from_path(str(ssh_config_path))
+    ssh_config_writer = SSHConfigWriter(ssh_config_path)
+
     mila_username: str = _get_mila_username(ssh_config)
     drac_username: str | None = _get_drac_username(ssh_config)
-    orig_config = ssh_config.cfg.config()
+
+    orig_config = ssh_config_writer.cfg.config()
 
     for hostname, entry in MILA_ENTRIES.copy().items():
         entry.update(User=mila_username)
-        _add_ssh_entry(ssh_config, hostname, entry)
+        _add_ssh_entry(ssh_config_writer, hostname, entry)
         _make_controlpath_dir(entry)
 
     if drac_username:
@@ -150,31 +185,31 @@ def setup_ssh_config(
         )
         for hostname, entry in DRAC_ENTRIES.copy().items():
             entry.update(User=drac_username)
-            _add_ssh_entry(ssh_config, hostname, entry)
+            _add_ssh_entry(ssh_config_writer, hostname, entry)
             _make_controlpath_dir(entry)
 
     # Check for *.server.mila.quebec in ssh config, to connect to compute nodes
     old_cnode_pattern = "*.server.mila.quebec"
 
-    if old_cnode_pattern in ssh_config.hosts():
+    if old_cnode_pattern in ssh_config_writer.hosts():
         logger.info(
             f"The '{old_cnode_pattern}' entry in ~/.ssh/config is too general and "
             "should exclude login.server.mila.quebec. Fixing this."
         )
-        ssh_config.remove(old_cnode_pattern)
+        ssh_config_writer.remove(old_cnode_pattern)
 
-    new_config = ssh_config.cfg.config()
+    new_config = ssh_config_writer.cfg.config()
     if orig_config == new_config:
         print("Did not change ssh config")
-    elif not _confirm_changes(ssh_config, previous=orig_config):
+    elif not _confirm_changes(ssh_config_writer, previous=orig_config):
         exit("Did not change ssh config")
     else:
-        ssh_config.save()
+        ssh_config_writer.save()
         print(f"Wrote {ssh_config_path}")
     return ssh_config
 
 
-def setup_windows_ssh_config_from_wsl(linux_ssh_config: SSHConfig):
+def setup_windows_ssh_config_from_wsl(linux_ssh_config_path: PosixPath):
     """Setup the Windows SSH configuration and public key from within WSL.
 
     This copies over the entries from the linux ssh configuration file, except for the
@@ -186,6 +221,8 @@ def setup_windows_ssh_config_from_wsl(linux_ssh_config: SSHConfig):
     This makes it so the user doesn't need to install Python/Anaconda on the Windows
     side in order to use `mila code` from within WSL.
     """
+    linux_ssh_config = SSHConfigWriter(linux_ssh_config_path)
+
     assert running_inside_WSL()
     # NOTE: This also assumes that a public/private key pair has already been generated
     # at ~/.ssh/id_rsa.pub and ~/.ssh/id_rsa.
@@ -193,7 +230,7 @@ def setup_windows_ssh_config_from_wsl(linux_ssh_config: SSHConfig):
     windows_ssh_config_path = windows_home / ".ssh/config"
     windows_ssh_config_path = _setup_ssh_config_file(windows_ssh_config_path)
 
-    windows_ssh_config = SSHConfig(windows_ssh_config_path)
+    windows_ssh_config = SSHConfigWriter(windows_ssh_config_path)
 
     initial_windows_config_contents = windows_ssh_config.cfg.config()
     _copy_valid_ssh_entries_to_windows_ssh_config_file(
@@ -228,7 +265,7 @@ def setup_windows_ssh_config_from_wsl(linux_ssh_config: SSHConfig):
         _copy_if_needed(linux_key_file, windows_key_file)
 
 
-def setup_passwordless_ssh_access(ssh_config: SSHConfig) -> bool:
+def setup_passwordless_ssh_access(ssh_config_path: Path) -> bool:
     """Sets up passwordless ssh access to the Mila and optionally also to DRAC.
 
     Sets up ssh connection to the DRAC clusters if they are present in the SSH config
@@ -236,37 +273,26 @@ def setup_passwordless_ssh_access(ssh_config: SSHConfig) -> bool:
 
     Returns whether the operation completed successfully or not.
     """
-    print("Checking passwordless authentication")
+    print("Setting up passwordless SSH access.")
 
-    here = LocalV1()
-    sshdir = Path.home() / ".ssh"
+    ssh_config = SSHConfigReader.from_path(str(ssh_config_path))
 
-    # Check if there is a public key file in ~/.ssh
-    if not list(sshdir.glob("id*.pub")):
-        if yn("You have no public keys. Generate one?"):
-            # Run ssh-keygen with the given location and no passphrase.
-            ssh_private_key_path = Path.home() / ".ssh" / "id_rsa"
-            create_ssh_keypair(ssh_private_key_path, here)
-        else:
-            print("No public keys.")
-            return False
+    # TODO: Generate SSH keys with ssh-keygen (not setting the passphrase so users can choose to use a passphrase or not).
+    setup_passwordless_ssh_access_to_cluster("mila", ssh_config_path)
 
-    # TODO: This uses the public key set in the SSH config file, which may (or may not)
-    # be the random id*.pub file that was just checked for above.
-    success = setup_passwordless_ssh_access_to_cluster("mila")
-    if not success:
-        return False
-    setup_keys_on_login_node("mila")
+    hosts_in_ssh_config = [
+        hostname
+        for hostname in ssh_config.get_hostnames()
+        if not any(c in hostname for c in "!*?")
+    ]
 
-    drac_clusters_in_ssh_config: list[str] = []
-    hosts_in_config = ssh_config.hosts()
-    for cluster in DRAC_CLUSTERS:
-        if any(cluster in hostname for hostname in hosts_in_config):
-            drac_clusters_in_ssh_config.append(cluster)
+    drac_clusters_in_ssh_config: list[str] = list(
+        set(DRAC_CLUSTERS).intersection(hosts_in_ssh_config)
+    )
 
     if not drac_clusters_in_ssh_config:
         logger.debug(
-            f"There are no DRAC clusters in the SSH config at {ssh_config.path}."
+            f"There are no DRAC clusters in the SSH config at {ssh_config_path}."
         )
         return True
 
@@ -279,14 +305,32 @@ def setup_passwordless_ssh_access(ssh_config: SSHConfig) -> bool:
         "See https://docs.alliancecan.ca/wiki/SSH_Keys#Using_CCDB for more info."
     )
     for drac_cluster in drac_clusters_in_ssh_config:
-        success = setup_passwordless_ssh_access_to_cluster(drac_cluster)
+        success = setup_passwordless_ssh_access_to_cluster(
+            drac_cluster, ssh_config_path
+        )
         if not success:
             return False
         setup_keys_on_login_node(drac_cluster)
     return True
 
 
-def setup_passwordless_ssh_access_to_cluster(cluster: str) -> bool:
+def _get_private_key_path_for_hostname(
+    hostname: str, ssh_config_path: Path
+) -> Path | None:
+    config = SSHConfigReader.from_path(str(ssh_config_path))
+    identity_file = config.lookup(hostname).get("identityfile")
+    if not identity_file:
+        return None
+    # Seems to be a list for some reason?
+    if isinstance(identity_file, list):
+        assert identity_file
+        identity_file = identity_file[0]
+    return Path(identity_file).expanduser()
+
+
+def setup_passwordless_ssh_access_to_cluster(
+    cluster: str, ssh_config_path: Path
+) -> bool:
     """Sets up passwordless SSH access to the given hostname.
 
     On Mac/Linux, uses `ssh-copy-id`. Performs the steps of ssh-copy-id manually on
@@ -294,21 +338,31 @@ def setup_passwordless_ssh_access_to_cluster(cluster: str) -> bool:
 
     Returns whether the operation completed successfully or not.
     """
-    here = LocalV1()
+    here = LocalV2()
     # Check that it is possible to connect without using a password.
     print(f"Checking if passwordless SSH access is setup for the {cluster} cluster.")
-    # TODO: Potentially use a custom key like `~/.ssh/id_milatools.pub` instead of
-    # the default.
+    ssh_private_key_path = _get_private_key_path_for_hostname(cluster, ssh_config_path)
+    # TODO: Simplify the code here by assuming that users just accepted the changes to
+    # their SSH config proposed by the first part of `mila init`.
+    # - Instead of making the code complicated with lots of corner cases, just raise an
+    #   error if the SSH config doesn't match what we expect to see after `mila init`.
+    if ssh_private_key_path is None:
+        # TODO: What to do if there isn't a private key set in the SSH config, but there
+        # is already a private key in the SSH dir? (it would be used by ssh).
+        console.log(
+            f"There is no private key set to be used for the {cluster} cluster."
+        )
+        ssh_private_key_path = Path("~/.ssh/id_rsa").expanduser()
+
+    if not ssh_private_key_path.exists():
+        console.log(
+            f"The ssh key to use for host {cluster} does not exist at {ssh_private_key_path}. Creating it now."
+        )
+        create_ssh_keypair(ssh_private_key_path)
+    config_writer = SSHConfigWriter(ssh_config_path)
 
-    from paramiko.config import SSHConfig
+    config_writer.set(cluster, IdentityFile=str(ssh_private_key_path))
 
-    config = SSHConfig.from_path(str(SSH_CONFIG_FILE))
-    identity_file = config.lookup(cluster).get("identityfile", "~/.ssh/id_rsa")
-    # Seems to be a list for some reason?
-    if isinstance(identity_file, list):
-        assert identity_file
-        identity_file = identity_file[0]
-    ssh_private_key_path = Path(identity_file).expanduser()
     ssh_public_key_path = ssh_private_key_path.with_suffix(".pub")
     assert ssh_public_key_path.exists()
 
@@ -345,17 +399,21 @@ def setup_passwordless_ssh_access_to_cluster(cluster: str) -> bool:
             subprocess.run(command, check=True, text=False, stdin=f)
     else:
         here.run(
-            "ssh-copy-id",
-            "-i",
-            str(ssh_private_key_path),
-            "-o",
-            "StrictHostKeyChecking=no",
-            cluster,
-            check=True,
+            (
+                "ssh-copy-id",
+                "-i",
+                str(ssh_private_key_path),
+                "-o",
+                "StrictHostKeyChecking=no",
+                cluster,
+            ),
         )
 
     # double-check that this worked.
-    if not check_passwordless(cluster):
+    if not control_socket_is_running(
+        cluster,
+        control_path=get_controlpath_for(cluster, ssh_config_path=ssh_config_path),
+    ):
         print(f"'ssh-copy-id {cluster}' appears to have failed!")
         return False
     return True
@@ -443,7 +501,7 @@ def get_windows_home_path_in_wsl() -> Path:
 
 def create_ssh_keypair(
     ssh_private_key_path: Path,
-    local: LocalV1 | None = None,
+    local: LocalV2 | None = None,
     passphrase: str | None = "",
 ) -> None:
     """Creates a public/private key pair at the given path using ssh-keygen.
@@ -452,18 +510,17 @@ def create_ssh_keypair(
     Otherwise, if passphrase is an empty string, no passphrase will be used (default).
     If a string is passed, it is passed to ssh-keygen and used as the passphrase.
     """
-    local = local or LocalV1()
-    command = [
+    local = local or LocalV2()
+    command = (
         "ssh-keygen",
         "-f",
         str(ssh_private_key_path.expanduser()),
         "-t",
-        "rsa",
-    ]
+        "rsa",  # note: Could also let the user choose the type of encryption..
+    )
     if passphrase is not None:
-        command.extend(["-N", passphrase])
-    display(command)
-    subprocess.run(command, check=True)
+        command += ("-N", passphrase)
+    local.run(command, display=True)
 
 
 def has_passphrase(ssh_private_key_path: Path) -> bool:
@@ -613,30 +670,18 @@ def ask_to_confirm_changes(before: str, after: str, path: str | Path) -> bool:
     return yn("\nIs this OK?")
 
 
-def _confirm_changes(ssh_config: SSHConfig, previous: str) -> bool:
+def _confirm_changes(ssh_config: SSHConfigWriter, previous: str) -> bool:
     before = previous + "\n"
     after = ssh_config.cfg.config() + "\n"
     return ask_to_confirm_changes(before, after, ssh_config.path)
 
 
-def _get_mila_username(ssh_config: SSHConfig) -> str:
+def _get_mila_username(ssh_config: SSHConfigReader) -> str:
     # Check for a mila entry in ssh config
     # NOTE: This also supports the case where there's a 'HOST mila some_alias_for_mila'
     # entry.
     # NOTE: ssh_config.host(entry) returns an empty dictionary if there is no entry.
-    username: str | None = None
-    hosts_with_mila_in_name_and_a_user_entry = [
-        host
-        for host in ssh_config.hosts()
-        if "mila" in host.split() and "user" in ssh_config.host(host)
-    ]
-    # Note: If there are none, or more than one, then we'll ask the user for their
-    # username, just to be sure.
-    if len(hosts_with_mila_in_name_and_a_user_entry) == 1:
-        username = ssh_config.host(hosts_with_mila_in_name_and_a_user_entry[0]).get(
-            "user"
-        )
-
+    username: str | None = ssh_config.lookup("mila").get("user")
     while not username:
         username = qn.text(
             "What's your username on the mila cluster?\n",
@@ -645,36 +690,32 @@ def _get_mila_username(ssh_config: SSHConfig) -> str:
     return username.strip()
 
 
-def _get_drac_username(ssh_config: SSHConfig) -> str | None:
+def _get_drac_username(ssh_config: SSHConfigReader) -> str | None:
     """Retrieve or ask the user for their username on the ComputeCanada/DRAC
     clusters."""
     # Check for one of the DRAC entries in ssh config
-    username: str | None = None
-    hosts_with_cluster_in_name_and_a_user_entry = [
-        host
-        for host in ssh_config.hosts()
-        if any(
-            cc_cluster in host.split() or f"!{cc_cluster}" in host.split()
-            for cc_cluster in DRAC_CLUSTERS
-        )
-        and "user" in ssh_config.host(host)
-    ]
-    users_from_drac_config_entries = set(
-        ssh_config.host(host)["user"]
-        for host in hosts_with_cluster_in_name_and_a_user_entry
+    users_from_drac_config_entries: set[str] = set(
+        drac_cluster_username
+        for drac_cluster in DRAC_CLUSTERS
+        if (drac_cluster_username := ssh_config.lookup(drac_cluster).get("user"))
+        is not None
     )
+    if len(users_from_drac_config_entries) == 1:
+        return users_from_drac_config_entries.pop().strip()
+
+    username: str | None = None
     # Note: If there are none, or more than one, then we'll ask the user for their
     # username, just to be sure.
-    if len(users_from_drac_config_entries) == 1:
-        username = users_from_drac_config_entries.pop()
-    elif yn("Do you also have an account on the ComputeCanada/DRAC clusters?"):
-        while not username:
-            username = qn.text(
+    if yn("Do you also have an account on the ComputeCanada/DRAC clusters?"):
+        while not (
+            username := qn.text(
                 "What's your username on the CC/DRAC clusters?\n",
                 validate=functools.partial(
                     _is_valid_username, cluster_name="ComputeCanada/DRAC clusters"
                 ),
             ).unsafe_ask()
+        ):
+            pass
     return username.strip() if username else None
 
 
@@ -693,7 +734,7 @@ def _is_valid_username(text: str, cluster_name: str = "mila cluster") -> bool |
 
 
 def _add_ssh_entry(
-    ssh_config: SSHConfig,
+    ssh_config: SSHConfigWriter,
     host: str,
     entry: dict[str, str | int],
     *,
@@ -728,7 +769,7 @@ def _add_ssh_entry(
 
 
 def _copy_valid_ssh_entries_to_windows_ssh_config_file(
-    linux_ssh_config: SSHConfig, windows_ssh_config: SSHConfig
+    linux_ssh_config: SSHConfigWriter, windows_ssh_config: SSHConfigWriter
 ):
     unsupported_keys_lowercase = set(k.lower() for k in WINDOWS_UNSUPPORTED_KEYS)
 
diff --git a/milatools/utils/local_v1.py b/milatools/utils/local_v1.py
index 6f5520bc..8f465059 100644
--- a/milatools/utils/local_v1.py
+++ b/milatools/utils/local_v1.py
@@ -1,19 +1,14 @@
 from __future__ import annotations
 
 import shlex
-import socket
 import subprocess
-import sys
 from logging import getLogger as get_logger
 from subprocess import CompletedProcess
 from typing import IO, Any
 
-import fabric
-import paramiko.ssh_exception
 from typing_extensions import deprecated
 
-from milatools.cli.utils import CommandNotFoundError, T, cluster_to_connect_kwargs
-from milatools.utils.remote_v2 import SSH_CONFIG_FILE, is_already_logged_in
+from milatools.cli.utils import CommandNotFoundError, T
 
 logger = get_logger(__name__)
 
@@ -69,9 +64,6 @@ def popen(
             cmd, stdout=stdout, stderr=stderr, universal_newlines=True
         )
 
-    def check_passwordless(self, host: str):
-        return check_passwordless(host)
-
 
 def display(split_command: list[str] | tuple[str, ...] | str) -> None:
     if isinstance(split_command, str):
@@ -79,44 +71,3 @@ def display(split_command: list[str] | tuple[str, ...] | str) -> None:
     else:
         command = shlex.join(split_command)
     print(T.bold_green("(local) $ ", command))
-
-
-def check_passwordless(host: str) -> bool:
-    if (
-        sys.platform != "win32"
-        and SSH_CONFIG_FILE.exists()
-        and is_already_logged_in(host, ssh_config_path=SSH_CONFIG_FILE)
-    ):
-        return True
-
-    try:
-        connect_kwargs_for_host = {"allow_agent": False}
-        if host in cluster_to_connect_kwargs:
-            connect_kwargs_for_host.update(cluster_to_connect_kwargs[host])
-        with fabric.Connection(
-            host,
-            connect_kwargs=connect_kwargs_for_host,
-        ) as connection:
-            results: fabric.runners.Result = connection.run(
-                "echo OK",
-                in_stream=False,
-                echo=True,
-                echo_format=T.bold_cyan(f"({host})" + " $ {command}"),
-            )
-
-    except (
-        paramiko.ssh_exception.SSHException,
-        paramiko.ssh_exception.NoValidConnectionsError,
-        socket.gaierror,
-        # BUG: Also getting ValueError("q must be exactlu 160, 224, or 256 bits long")
-        # with older versions of paramiko.
-        # ValueError,
-    ) as err:
-        logger.debug(f"Unable to connect to {host} without a password: {err}")
-        return False
-
-    if "OK" in results.stdout:
-        return True
-    logger.error("Unexpected output from SSH command, output didn't contain 'OK'!")
-    logger.error(f"stdout: {results.stdout}, stderr: {results.stderr}")
-    return False
diff --git a/tests/cli/test_init_command.py b/tests/cli/test_init.py
similarity index 97%
rename from tests/cli/test_init_command.py
rename to tests/cli/test_init.py
index 2825c3cf..2cf3e112 100644
--- a/tests/cli/test_init_command.py
+++ b/tests/cli/test_init.py
@@ -11,7 +11,7 @@
 import textwrap
 from functools import partial
 from logging import getLogger as get_logger
-from pathlib import Path, PurePosixPath
+from pathlib import Path, PosixPath, PurePosixPath
 from unittest.mock import Mock
 
 import invoke
@@ -22,8 +22,8 @@
 from prompt_toolkit.input import PipeInput, create_pipe_input
 from pytest_regressions.file_regression import FileRegressionFixture
 
-from milatools.cli import init_command
-from milatools.cli.init_command import (
+from milatools.cli import init
+from milatools.cli.init import (
     DRAC_CLUSTERS,
     _get_drac_username,
     _get_mila_username,
@@ -42,7 +42,7 @@
     SSHConfig,
     running_inside_WSL,
 )
-from milatools.utils.local_v1 import LocalV1, check_passwordless
+from milatools.utils.local_v1 import LocalV1
 from milatools.utils.remote_v1 import RemoteV1
 from milatools.utils.remote_v2 import (
     SSH_CACHE_DIR,
@@ -542,8 +542,8 @@ def test_with_existing_entries(
                     User Bob
                 """
             ),
-            ["bob\r"],
-            "bob",
+            [],  # user input doesn't matter (won't get asked).
+            "george",
             id="two_matching_entries",
         ),
         pytest.param(
@@ -579,7 +579,7 @@ def test_get_username(
     ssh_config_path = tmp_path / "config"
     with open(ssh_config_path, "w") as f:
         f.write(contents)
-    ssh_config = SSHConfig(ssh_config_path)
+    ssh_config = paramiko.SSHConfig.from_path(str(ssh_config_path))
     if not prompt_inputs:
         input_pipe.close()
     for prompt_input in prompt_inputs:
@@ -639,8 +639,8 @@ def test_get_username(
                     User Bob
                 """
             ),
-            ["y", "bob\r"],
-            "bob",
+            [],  # will not get asked for input.
+            "george",
             id="two_matching_entries",
         ),
         pytest.param(
@@ -675,7 +675,7 @@ def test_get_drac_username(
     ssh_config_path = tmp_path / "config"
     with open(ssh_config_path, "w") as f:
         f.write(contents)
-    ssh_config = SSHConfig(ssh_config_path)
+    ssh_config = paramiko.SSHConfig.from_path(str(ssh_config_path))
     if not prompt_inputs:
         input_pipe.close()
     for prompt_input in prompt_inputs:
@@ -845,12 +845,12 @@ def test_setup_windows_ssh_config_from_wsl(
     windows_ssh_config_path = windows_home / ".ssh" / "config"
 
     monkeypatch.setattr(
-        init_command,
+        init,
         running_inside_WSL.__name__,
         Mock(spec=running_inside_WSL, return_value=True),
     )
     monkeypatch.setattr(
-        init_command,
+        init,
         get_windows_home_path_in_wsl.__name__,
         Mock(spec=get_windows_home_path_in_wsl, return_value=windows_home),
     )
@@ -863,7 +863,9 @@ def test_setup_windows_ssh_config_from_wsl(
     for prompt in user_inputs:
         input_pipe.send_text(prompt)
 
-    setup_windows_ssh_config_from_wsl(linux_ssh_config=linux_ssh_config)
+    setup_windows_ssh_config_from_wsl(
+        linux_ssh_config_path=PosixPath(linux_ssh_config.path)
+    )
 
     assert windows_ssh_config_path.exists()
     assert windows_ssh_config_path.stat().st_mode & 0o777 == 0o600
@@ -921,15 +923,15 @@ def test_setup_vscode_settings(
             json.dump(initial_settings, f, indent=4)
 
     monkeypatch.setattr(
-        init_command,
-        init_command.vscode_installed.__name__,
-        Mock(spec=init_command.vscode_installed, return_value=True),
+        init,
+        init.vscode_installed.__name__,
+        Mock(spec=init.vscode_installed, return_value=True),
     )
     monkeypatch.setattr(
-        init_command,
-        init_command.get_expected_vscode_settings_json_path.__name__,
+        init,
+        init.get_expected_vscode_settings_json_path.__name__,
         Mock(
-            spec=init_command.get_expected_vscode_settings_json_path,
+            spec=init.get_expected_vscode_settings_json_path,
             return_value=vscode_settings_json_path,
         ),
     )
@@ -1005,12 +1007,12 @@ def test_setup_windows_ssh_config_from_wsl_copies_keys(
     monkeypatch.setattr(Path, "home", Mock(spec=Path.home, return_value=linux_home))
 
     monkeypatch.setattr(
-        init_command,
+        init,
         running_inside_WSL.__name__,
         Mock(spec=running_inside_WSL, return_value=True),
     )
     monkeypatch.setattr(
-        init_command,
+        init,
         get_windows_home_path_in_wsl.__name__,
         Mock(spec=get_windows_home_path_in_wsl, return_value=windows_home),
     )
@@ -1029,7 +1031,9 @@ def test_setup_windows_ssh_config_from_wsl_copies_keys(
     input_pipe.send_text("y")  # accept creating the Windows config file
     input_pipe.send_text("y")  # accept the changes
 
-    setup_windows_ssh_config_from_wsl(linux_ssh_config=linux_ssh_config)
+    setup_windows_ssh_config_from_wsl(
+        linux_ssh_config_path=PosixPath(linux_ssh_config.path)
+    )
 
     windows_private_key_path = windows_home / ".ssh" / "id_rsa"
     windows_public_key_path = windows_private_key_path.with_suffix(".pub")
@@ -1283,8 +1287,6 @@ def test_setup_passwordless_ssh_access_to_cluster(
     assert ssh_public_key_path.exists()
 
     def have_passwordless_ssh_access_to(cluster: str) -> bool:
-        if sys.platform == "win32":
-            return check_passwordless(cluster)
         return is_already_logged_in(cluster, ssh_config_path=SSH_CONFIG_FILE)
 
     def _exists(file: PurePosixPath | Path):
@@ -1340,7 +1342,7 @@ def temporarily_disable_ssh_access_to_cluster():
                 # subprocess.check_call(
                 #     ["ssh", "-O", "exit", f"-oControlPath={control_path}", cluster]
                 # )
-            assert not check_passwordless(cluster)
+            assert not is_already_logged_in(cluster)
         else:
             assert passwordless_ssh_was_previously_setup
             if _exists(authorized_keys_file):
@@ -1356,7 +1358,7 @@ def temporarily_disable_ssh_access_to_cluster():
                     hide=False,
                 )
             # todo: might not work well for the DRAC clusters!
-            assert not check_passwordless(cluster)
+            assert not is_already_logged_in(cluster)
 
     def reenable_ssh_access_to_cluster():
         if cluster == "localhost":
@@ -1376,7 +1378,7 @@ def reenable_ssh_access_to_cluster():
                 ssh_dir.mkdir(exist_ok=True, mode=0o700)
                 assert not passwordless_ssh_was_previously_setup
                 shutil.copy(backup_authorized_keys_file, authorized_keys_file)
-            assert check_passwordless(cluster)
+            assert is_already_logged_in(cluster)
         else:
             logger.info(
                 f"Restoring the original {authorized_keys_file} from backup at "
@@ -1570,16 +1572,16 @@ def test_setup_passwordless_ssh_access(
         spec=setup_passwordless_ssh_access_to_cluster,
         side_effect=[accept_mila, *(accept_drac for _ in drac_clusters_in_ssh_config)],
     )
-    import milatools.cli.init_command
+    import milatools.cli.init
 
     monkeypatch.setattr(
-        milatools.cli.init_command,
+        milatools.cli.init,
         setup_passwordless_ssh_access_to_cluster.__name__,
         mock_setup_passwordless_ssh_access_to_cluster,
     )
 
     monkeypatch.setattr(
-        milatools.cli.init_command,
+        milatools.cli.init,
         setup_keys_on_login_node.__name__,
         Mock(spec=setup_keys_on_login_node),
     )
diff --git a/tests/cli/test_init_command/test_fixes_overly_general_entry.txt b/tests/cli/test_init/test_fixes_overly_general_entry.txt
similarity index 100%
rename from tests/cli/test_init_command/test_fixes_overly_general_entry.txt
rename to tests/cli/test_init/test_fixes_overly_general_entry.txt
diff --git a/tests/cli/test_init_command/test_setup_passwordless_ssh_access_to_cluster_localhost_accept_registering_key_already_setup_.md b/tests/cli/test_init/test_setup_passwordless_ssh_access_to_cluster_localhost_accept_registering_key_already_setup_.md
similarity index 100%
rename from tests/cli/test_init_command/test_setup_passwordless_ssh_access_to_cluster_localhost_accept_registering_key_already_setup_.md
rename to tests/cli/test_init/test_setup_passwordless_ssh_access_to_cluster_localhost_accept_registering_key_already_setup_.md
diff --git a/tests/cli/test_init_command/test_setup_passwordless_ssh_access_to_cluster_localhost_accept_registering_key_not_already_setup_.md b/tests/cli/test_init/test_setup_passwordless_ssh_access_to_cluster_localhost_accept_registering_key_not_already_setup_.md
similarity index 100%
rename from tests/cli/test_init_command/test_setup_passwordless_ssh_access_to_cluster_localhost_accept_registering_key_not_already_setup_.md
rename to tests/cli/test_init/test_setup_passwordless_ssh_access_to_cluster_localhost_accept_registering_key_not_already_setup_.md
diff --git a/tests/cli/test_init_command/test_setup_passwordless_ssh_access_to_cluster_localhost_reject_registering_key_already_setup_.md b/tests/cli/test_init/test_setup_passwordless_ssh_access_to_cluster_localhost_reject_registering_key_already_setup_.md
similarity index 100%
rename from tests/cli/test_init_command/test_setup_passwordless_ssh_access_to_cluster_localhost_reject_registering_key_already_setup_.md
rename to tests/cli/test_init/test_setup_passwordless_ssh_access_to_cluster_localhost_reject_registering_key_already_setup_.md
diff --git a/tests/cli/test_init_command/test_setup_passwordless_ssh_access_to_cluster_localhost_reject_registering_key_not_already_setup_.md b/tests/cli/test_init/test_setup_passwordless_ssh_access_to_cluster_localhost_reject_registering_key_not_already_setup_.md
similarity index 100%
rename from tests/cli/test_init_command/test_setup_passwordless_ssh_access_to_cluster_localhost_reject_registering_key_not_already_setup_.md
rename to tests/cli/test_init/test_setup_passwordless_ssh_access_to_cluster_localhost_reject_registering_key_not_already_setup_.md
diff --git a/tests/cli/test_init_command/test_setup_ssh_empty_confirm_changes_drac_.md b/tests/cli/test_init/test_setup_ssh_empty_confirm_changes_drac_.md
similarity index 100%
rename from tests/cli/test_init_command/test_setup_ssh_empty_confirm_changes_drac_.md
rename to tests/cli/test_init/test_setup_ssh_empty_confirm_changes_drac_.md
diff --git a/tests/cli/test_init_command/test_setup_ssh_empty_confirm_changes_no_drac_.md b/tests/cli/test_init/test_setup_ssh_empty_confirm_changes_no_drac_.md
similarity index 100%
rename from tests/cli/test_init_command/test_setup_ssh_empty_confirm_changes_no_drac_.md
rename to tests/cli/test_init/test_setup_ssh_empty_confirm_changes_no_drac_.md
diff --git a/tests/cli/test_init_command/test_setup_ssh_empty_reject_changes_drac_.md b/tests/cli/test_init/test_setup_ssh_empty_reject_changes_drac_.md
similarity index 100%
rename from tests/cli/test_init_command/test_setup_ssh_empty_reject_changes_drac_.md
rename to tests/cli/test_init/test_setup_ssh_empty_reject_changes_drac_.md
diff --git a/tests/cli/test_init_command/test_setup_ssh_empty_reject_changes_no_drac_.md b/tests/cli/test_init/test_setup_ssh_empty_reject_changes_no_drac_.md
similarity index 100%
rename from tests/cli/test_init_command/test_setup_ssh_empty_reject_changes_no_drac_.md
rename to tests/cli/test_init/test_setup_ssh_empty_reject_changes_no_drac_.md
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_confirm_changes_drac_.md b/tests/cli/test_init/test_setup_ssh_has_comment_and_entry_confirm_changes_drac_.md
similarity index 100%
rename from tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_confirm_changes_drac_.md
rename to tests/cli/test_init/test_setup_ssh_has_comment_and_entry_confirm_changes_drac_.md
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_confirm_changes_no_drac_.md b/tests/cli/test_init/test_setup_ssh_has_comment_and_entry_confirm_changes_no_drac_.md
similarity index 100%
rename from tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_confirm_changes_no_drac_.md
rename to tests/cli/test_init/test_setup_ssh_has_comment_and_entry_confirm_changes_no_drac_.md
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_reject_changes_drac_.md b/tests/cli/test_init/test_setup_ssh_has_comment_and_entry_reject_changes_drac_.md
similarity index 100%
rename from tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_reject_changes_drac_.md
rename to tests/cli/test_init/test_setup_ssh_has_comment_and_entry_reject_changes_drac_.md
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_reject_changes_no_drac_.md b/tests/cli/test_init/test_setup_ssh_has_comment_and_entry_reject_changes_no_drac_.md
similarity index 100%
rename from tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_reject_changes_no_drac_.md
rename to tests/cli/test_init/test_setup_ssh_has_comment_and_entry_reject_changes_no_drac_.md
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_with_extra_space_confirm_changes_drac_.md b/tests/cli/test_init/test_setup_ssh_has_comment_and_entry_with_extra_space_confirm_changes_drac_.md
similarity index 100%
rename from tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_with_extra_space_confirm_changes_drac_.md
rename to tests/cli/test_init/test_setup_ssh_has_comment_and_entry_with_extra_space_confirm_changes_drac_.md
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_with_extra_space_confirm_changes_no_drac_.md b/tests/cli/test_init/test_setup_ssh_has_comment_and_entry_with_extra_space_confirm_changes_no_drac_.md
similarity index 100%
rename from tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_with_extra_space_confirm_changes_no_drac_.md
rename to tests/cli/test_init/test_setup_ssh_has_comment_and_entry_with_extra_space_confirm_changes_no_drac_.md
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_with_extra_space_reject_changes_drac_.md b/tests/cli/test_init/test_setup_ssh_has_comment_and_entry_with_extra_space_reject_changes_drac_.md
similarity index 100%
rename from tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_with_extra_space_reject_changes_drac_.md
rename to tests/cli/test_init/test_setup_ssh_has_comment_and_entry_with_extra_space_reject_changes_drac_.md
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_with_extra_space_reject_changes_no_drac_.md b/tests/cli/test_init/test_setup_ssh_has_comment_and_entry_with_extra_space_reject_changes_no_drac_.md
similarity index 100%
rename from tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_with_extra_space_reject_changes_no_drac_.md
rename to tests/cli/test_init/test_setup_ssh_has_comment_and_entry_with_extra_space_reject_changes_no_drac_.md
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_comment_confirm_changes_drac_.md b/tests/cli/test_init/test_setup_ssh_has_comment_confirm_changes_drac_.md
similarity index 100%
rename from tests/cli/test_init_command/test_setup_ssh_has_comment_confirm_changes_drac_.md
rename to tests/cli/test_init/test_setup_ssh_has_comment_confirm_changes_drac_.md
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_comment_confirm_changes_no_drac_.md b/tests/cli/test_init/test_setup_ssh_has_comment_confirm_changes_no_drac_.md
similarity index 100%
rename from tests/cli/test_init_command/test_setup_ssh_has_comment_confirm_changes_no_drac_.md
rename to tests/cli/test_init/test_setup_ssh_has_comment_confirm_changes_no_drac_.md
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_comment_reject_changes_drac_.md b/tests/cli/test_init/test_setup_ssh_has_comment_reject_changes_drac_.md
similarity index 100%
rename from tests/cli/test_init_command/test_setup_ssh_has_comment_reject_changes_drac_.md
rename to tests/cli/test_init/test_setup_ssh_has_comment_reject_changes_drac_.md
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_comment_reject_changes_no_drac_.md b/tests/cli/test_init/test_setup_ssh_has_comment_reject_changes_no_drac_.md
similarity index 100%
rename from tests/cli/test_init_command/test_setup_ssh_has_comment_reject_changes_no_drac_.md
rename to tests/cli/test_init/test_setup_ssh_has_comment_reject_changes_no_drac_.md
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_different_indent_confirm_changes_drac_.md b/tests/cli/test_init/test_setup_ssh_has_different_indent_confirm_changes_drac_.md
similarity index 100%
rename from tests/cli/test_init_command/test_setup_ssh_has_different_indent_confirm_changes_drac_.md
rename to tests/cli/test_init/test_setup_ssh_has_different_indent_confirm_changes_drac_.md
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_different_indent_confirm_changes_no_drac_.md b/tests/cli/test_init/test_setup_ssh_has_different_indent_confirm_changes_no_drac_.md
similarity index 100%
rename from tests/cli/test_init_command/test_setup_ssh_has_different_indent_confirm_changes_no_drac_.md
rename to tests/cli/test_init/test_setup_ssh_has_different_indent_confirm_changes_no_drac_.md
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_different_indent_reject_changes_drac_.md b/tests/cli/test_init/test_setup_ssh_has_different_indent_reject_changes_drac_.md
similarity index 100%
rename from tests/cli/test_init_command/test_setup_ssh_has_different_indent_reject_changes_drac_.md
rename to tests/cli/test_init/test_setup_ssh_has_different_indent_reject_changes_drac_.md
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_different_indent_reject_changes_no_drac_.md b/tests/cli/test_init/test_setup_ssh_has_different_indent_reject_changes_no_drac_.md
similarity index 100%
rename from tests/cli/test_init_command/test_setup_ssh_has_different_indent_reject_changes_no_drac_.md
rename to tests/cli/test_init/test_setup_ssh_has_different_indent_reject_changes_no_drac_.md
diff --git a/tests/cli/test_init_command/test_setup_vscode_settings_accept_None_.md b/tests/cli/test_init/test_setup_vscode_settings_accept_None_.md
similarity index 100%
rename from tests/cli/test_init_command/test_setup_vscode_settings_accept_None_.md
rename to tests/cli/test_init/test_setup_vscode_settings_accept_None_.md
diff --git a/tests/cli/test_init_command/test_setup_vscode_settings_accept_initial_settings1_.md b/tests/cli/test_init/test_setup_vscode_settings_accept_initial_settings1_.md
similarity index 100%
rename from tests/cli/test_init_command/test_setup_vscode_settings_accept_initial_settings1_.md
rename to tests/cli/test_init/test_setup_vscode_settings_accept_initial_settings1_.md
diff --git a/tests/cli/test_init_command/test_setup_vscode_settings_accept_initial_settings2_.md b/tests/cli/test_init/test_setup_vscode_settings_accept_initial_settings2_.md
similarity index 100%
rename from tests/cli/test_init_command/test_setup_vscode_settings_accept_initial_settings2_.md
rename to tests/cli/test_init/test_setup_vscode_settings_accept_initial_settings2_.md
diff --git a/tests/cli/test_init_command/test_setup_vscode_settings_accept_initial_settings3_.md b/tests/cli/test_init/test_setup_vscode_settings_accept_initial_settings3_.md
similarity index 100%
rename from tests/cli/test_init_command/test_setup_vscode_settings_accept_initial_settings3_.md
rename to tests/cli/test_init/test_setup_vscode_settings_accept_initial_settings3_.md
diff --git a/tests/cli/test_init_command/test_setup_vscode_settings_accept_initial_settings4_.md b/tests/cli/test_init/test_setup_vscode_settings_accept_initial_settings4_.md
similarity index 100%
rename from tests/cli/test_init_command/test_setup_vscode_settings_accept_initial_settings4_.md
rename to tests/cli/test_init/test_setup_vscode_settings_accept_initial_settings4_.md
diff --git a/tests/cli/test_init_command/test_setup_windows_ssh_config_from_wsl_accept_.md b/tests/cli/test_init/test_setup_windows_ssh_config_from_wsl_accept_.md
similarity index 100%
rename from tests/cli/test_init_command/test_setup_windows_ssh_config_from_wsl_accept_.md
rename to tests/cli/test_init/test_setup_windows_ssh_config_from_wsl_accept_.md
diff --git a/tests/cli/test_init_command/test_setup_windows_ssh_config_from_wsl_reject_.md b/tests/cli/test_init/test_setup_windows_ssh_config_from_wsl_reject_.md
similarity index 100%
rename from tests/cli/test_init_command/test_setup_windows_ssh_config_from_wsl_reject_.md
rename to tests/cli/test_init/test_setup_windows_ssh_config_from_wsl_reject_.md
diff --git a/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_has_drac_entries_.md b/tests/cli/test_init/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_has_drac_entries_.md
similarity index 100%
rename from tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_has_drac_entries_.md
rename to tests/cli/test_init/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_has_drac_entries_.md
diff --git a/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_no_drac_entries_.md b/tests/cli/test_init/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_no_drac_entries_.md
similarity index 100%
rename from tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_no_drac_entries_.md
rename to tests/cli/test_init/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_no_drac_entries_.md
diff --git a/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_has_drac_entries_.md b/tests/cli/test_init/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_has_drac_entries_.md
similarity index 100%
rename from tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_has_drac_entries_.md
rename to tests/cli/test_init/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_has_drac_entries_.md
diff --git a/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_no_drac_entries_.md b/tests/cli/test_init/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_no_drac_entries_.md
similarity index 100%
rename from tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_no_drac_entries_.md
rename to tests/cli/test_init/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_no_drac_entries_.md
diff --git a/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_has_drac_entries_.md b/tests/cli/test_init/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_has_drac_entries_.md
similarity index 100%
rename from tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_has_drac_entries_.md
rename to tests/cli/test_init/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_has_drac_entries_.md
diff --git a/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_no_drac_entries_.md b/tests/cli/test_init/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_no_drac_entries_.md
similarity index 100%
rename from tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_no_drac_entries_.md
rename to tests/cli/test_init/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_no_drac_entries_.md
diff --git a/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_has_drac_entries_.md b/tests/cli/test_init/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_has_drac_entries_.md
similarity index 100%
rename from tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_has_drac_entries_.md
rename to tests/cli/test_init/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_has_drac_entries_.md
diff --git a/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_no_drac_entries_.md b/tests/cli/test_init/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_no_drac_entries_.md
similarity index 100%
rename from tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_no_drac_entries_.md
rename to tests/cli/test_init/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_no_drac_entries_.md
diff --git a/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_has_drac_entries_.md b/tests/cli/test_init/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_has_drac_entries_.md
similarity index 100%
rename from tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_has_drac_entries_.md
rename to tests/cli/test_init/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_has_drac_entries_.md
diff --git a/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_no_drac_entries_.md b/tests/cli/test_init/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_no_drac_entries_.md
similarity index 100%
rename from tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_no_drac_entries_.md
rename to tests/cli/test_init/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_no_drac_entries_.md
diff --git a/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_has_drac_entries_.md b/tests/cli/test_init/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_has_drac_entries_.md
similarity index 100%
rename from tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_has_drac_entries_.md
rename to tests/cli/test_init/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_has_drac_entries_.md
diff --git a/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_no_drac_entries_.md b/tests/cli/test_init/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_no_drac_entries_.md
similarity index 100%
rename from tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_no_drac_entries_.md
rename to tests/cli/test_init/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_no_drac_entries_.md
diff --git a/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_has_drac_entries_.md b/tests/cli/test_init/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_has_drac_entries_.md
similarity index 100%
rename from tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_has_drac_entries_.md
rename to tests/cli/test_init/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_has_drac_entries_.md
diff --git a/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_no_drac_entries_.md b/tests/cli/test_init/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_no_drac_entries_.md
similarity index 100%
rename from tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_no_drac_entries_.md
rename to tests/cli/test_init/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_no_drac_entries_.md
diff --git a/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_has_drac_entries_.md b/tests/cli/test_init/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_has_drac_entries_.md
similarity index 100%
rename from tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_has_drac_entries_.md
rename to tests/cli/test_init/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_has_drac_entries_.md
diff --git a/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_no_drac_entries_.md b/tests/cli/test_init/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_no_drac_entries_.md
similarity index 100%
rename from tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_no_drac_entries_.md
rename to tests/cli/test_init/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_no_drac_entries_.md
diff --git a/tests/conftest.py b/tests/conftest.py
index f74a8177..2c379b9f 100644
--- a/tests/conftest.py
+++ b/tests/conftest.py
@@ -25,7 +25,7 @@
 import milatools.utils.parallel_progress
 import milatools.utils.remote_v2
 from milatools.cli import console
-from milatools.cli.init_command import setup_ssh_config
+from milatools.cli.init import setup_ssh_config
 from milatools.cli.utils import SSH_CONFIG_FILE
 from milatools.utils.compute_node import get_queued_milatools_job_ids
 from milatools.utils.remote_v1 import RemoteV1
@@ -379,7 +379,7 @@ def ssh_config_file(
     monkeypatch: pytest.MonkeyPatch,
 ) -> Path:
     """Fixture that creates the SSH config as setup by `mila init`."""
-    from milatools.cli.init_command import yn
+    from milatools.cli.init import yn
 
     # NOTE: might want to put this in a fixture if we wanted the "real" mila / drac
     # usernames in the config.
@@ -400,9 +400,9 @@ def _yn(question: str) -> bool:
 
     mock_yn = Mock(spec=yn, side_effect=_yn)
 
-    import milatools.cli.init_command
+    import milatools.cli.init
 
-    monkeypatch.setattr(milatools.cli.init_command, yn.__name__, mock_yn)
+    monkeypatch.setattr(milatools.cli.init, yn.__name__, mock_yn)
 
     def _mock_unsafe_ask(question: str, *args, **kwargs) -> str:
         question = question.strip()
diff --git a/tests/utils/test_local_v1.py b/tests/utils/test_local_v1.py
index 6d04ae50..fa1f1f3d 100644
--- a/tests/utils/test_local_v1.py
+++ b/tests/utils/test_local_v1.py
@@ -1,22 +1,17 @@
 from __future__ import annotations
 
-import sys
 from subprocess import PIPE
 
 import pytest
 from pytest_regressions.file_regression import FileRegressionFixture
 
-from milatools.cli.utils import SSH_CONFIG_FILE
-from milatools.utils.local_v1 import CommandNotFoundError, LocalV1, check_passwordless
-from milatools.utils.remote_v2 import is_already_logged_in
+from milatools.utils.local_v1 import CommandNotFoundError, LocalV1
 
 from ..cli.common import (
     in_github_CI,
     in_self_hosted_github_CI,
     output_tester,
-    passwordless_ssh_connection_to_localhost_is_setup,
     requires_no_s_flag,
-    skip_if_on_github_cloud_CI,
     xfails_on_windows,
 )
 
@@ -129,70 +124,3 @@ def test_popen(
         "and raises a ValueError."
     ),
 )
-
-
-# @PARAMIKO_SSH_BANNER_BUG
-# @paramiko_openssh_key_parsing_issue
-@pytest.mark.xfail(
-    reason="TODO: `check_passwordless` is incredibly flaky and needs to be reworked."
-)
-@pytest.mark.parametrize(
-    ("hostname", "expected"),
-    [
-        pytest.param(
-            "localhost",
-            passwordless_ssh_connection_to_localhost_is_setup,
-        ),
-        ("blablabob@localhost", False),
-        pytest.param(
-            "mila",
-            True if (in_self_hosted_github_CI or not in_github_CI) else False,
-        ),
-        pytest.param(
-            "bobobobobobo@mila",
-            False,
-            marks=[
-                paramiko_openssh_key_parsing_issue,
-                skip_if_on_github_cloud_CI,
-            ],
-        ),
-        # For the clusters with 2FA, we expect `check_passwordless` to return True if
-        # we've already setup the shared SSH connection.
-        pytest.param(
-            "blablabob@narval",
-            False,
-            marks=[
-                skip_if_on_github_cloud_CI,
-                paramiko_openssh_key_parsing_issue,
-            ],
-        ),
-        *(
-            # note: can't properly test for the False case because of the 2FA
-            # prompt!
-            pytest.param(
-                drac_cluster,
-                True,
-                marks=pytest.mark.skipif(
-                    sys.platform == "win32"
-                    or not is_already_logged_in(
-                        drac_cluster, ssh_config_path=SSH_CONFIG_FILE
-                    ),
-                    reason="Should give True when we're already logged in.",
-                ),
-            )
-            for drac_cluster in ["narval", "beluga", "cedar", "graham"]
-        ),
-        pytest.param(
-            "niagara",
-            False,
-            marks=[
-                skip_if_on_github_cloud_CI,
-                paramiko_openssh_key_parsing_issue,
-            ],
-        ),  # SSH access to niagara isn't enabled by default.
-    ],
-)
-def test_check_passwordless(hostname: str, expected: bool):
-    # TODO: Maybe also test how `check_passwordless` behaves when using a key with a
-    # passphrase.
-    assert check_passwordless(hostname) == expected