diff --git a/pkgs/clan-cli/clan_cli/machines/install.py b/pkgs/clan-cli/clan_cli/machines/install.py
index d2f04529f..2c57ba4cb 100644
--- a/pkgs/clan-cli/clan_cli/machines/install.py
+++ b/pkgs/clan-cli/clan_cli/machines/install.py
@@ -24,12 +24,14 @@ def install_command(args: argparse.Namespace) -> None:
         # Only if the caller did not specify a target_host via args.target_host
         # Find a suitable target_host that is reachable
         target_host_str = args.target_host
-        deploy_info: DeployInfo | None = ssh_command_parse(args)
+        deploy_info: DeployInfo | None = (
+            ssh_command_parse(args) if target_host_str is None else None
+        )
 
         use_tor = False
-        if deploy_info and not args.target_host:
+        if deploy_info:
             host = find_reachable_host(deploy_info)
-            if host is None:
+            if host is None or host.tor_socks:
                 use_tor = True
                 target_host_str = deploy_info.tor.target
             else:
diff --git a/pkgs/clan-cli/clan_cli/ssh/deploy_info.py b/pkgs/clan-cli/clan_cli/ssh/deploy_info.py
index a3e9619b1..0838844d5 100644
--- a/pkgs/clan-cli/clan_cli/ssh/deploy_info.py
+++ b/pkgs/clan-cli/clan_cli/ssh/deploy_info.py
@@ -154,6 +154,7 @@ def ssh_shell_from_deploy(
 def ssh_command_parse(args: argparse.Namespace) -> DeployInfo | None:
     host_key_check = args.host_key_check
     deploy = None
+
     if args.json:
         json_file = Path(args.json)
         if json_file.is_file():
@@ -161,23 +162,25 @@ def ssh_command_parse(args: argparse.Namespace) -> DeployInfo | None:
             return DeployInfo.from_json(data, host_key_check)
         data = json.loads(args.json)
         deploy = DeployInfo.from_json(data, host_key_check)
-    if args.png:
+    elif args.png:
         deploy = DeployInfo.from_qr_code(Path(args.png), host_key_check)
-
-    if hasattr(args, "machine") and args.machine:
+    elif hasattr(args, "machine") and args.machine:
         machine = Machine(args.machine, args.flake)
         target = machine.target_host().override(
             command_prefix=machine.name, host_key_check=host_key_check
         )
         deploy = DeployInfo(addrs=[target])
-
-    if deploy is None:
+    else:
         return None
 
-    ssh_options = {}
-    for name, value in args.ssh_option or []:
-        ssh_options[name] = value
+    ssh_options = None
+    if hasattr(args, "ssh_option") and args.ssh_option:
+        for name, value in args.ssh_option:
+            ssh_options = {}
+            ssh_options[name] = value
+
     deploy = deploy.overwrite_remotes(ssh_options=ssh_options)
+
     return deploy
 
 
diff --git a/pkgs/clan-cli/clan_cli/ssh/test_deploy_info.py b/pkgs/clan-cli/clan_cli/ssh/test_deploy_info.py
index 0e274539a..30d758311 100644
--- a/pkgs/clan-cli/clan_cli/ssh/test_deploy_info.py
+++ b/pkgs/clan-cli/clan_cli/ssh/test_deploy_info.py
@@ -9,8 +9,6 @@ from clan_lib.ssh.remote import Remote
 from clan_cli.ssh.deploy_info import DeployInfo, find_reachable_host
 from clan_cli.tests.fixtures_flakes import ClanFlake
 from clan_cli.tests.helpers import cli
-from clan_cli.tests.nix_config import ConfigItem
-from clan_cli.tests.stdout import CaptureOutput
 
 
 def test_qrcode_scan(temp_dir: Path) -> None:
@@ -90,13 +88,11 @@ def test_find_reachable_host(hosts: list[Remote]) -> None:
 def test_ssh_shell_from_deploy(
     hosts: list[Remote],
     flake: ClanFlake,
-    nix_config: dict[str, ConfigItem],
-    capture_output: CaptureOutput,
 ) -> None:
     host = hosts[0]
 
     machine1_config = flake.machines["m1_machine"]
-    machine1_config["nixpkgs"]["hostPlatform"] = nix_config["system"].value
+    machine1_config["nixpkgs"]["hostPlatform"] = "x86_64-linux"
     machine1_config["clan"]["networking"]["targetHost"] = host.ssh_url()
     flake.refresh()
 
diff --git a/pkgs/clan-cli/clan_lib/ssh/remote.py b/pkgs/clan-cli/clan_lib/ssh/remote.py
index c42f70af6..9cf0c0cfa 100644
--- a/pkgs/clan-cli/clan_lib/ssh/remote.py
+++ b/pkgs/clan-cli/clan_lib/ssh/remote.py
@@ -454,7 +454,7 @@ class Remote:
 @dataclass(frozen=True)
 class ConnectionOptions:
     timeout: int = 2
-    retries: int = 10
+    retries: int = 5
 
 
 @dataclass
@@ -527,6 +527,10 @@ def check_machine_ssh_reachable(
     if opts is None:
         opts = ConnectionOptions()
 
+    cmdlog.debug(
+        f"Checking SSH reachability for {remote.target} on port {remote.port or 22}",
+    )
+
     address_family = socket.AF_INET6 if ":" in remote.address else socket.AF_INET
     for _ in range(opts.retries):
         with socket.socket(address_family, socket.SOCK_STREAM) as sock: