diff --git a/src/compose_farm/cli/management.py b/src/compose_farm/cli/management.py
index 417b37f..4f779a5 100644
--- a/src/compose_farm/cli/management.py
+++ b/src/compose_farm/cli/management.py
@@ -238,11 +238,16 @@ def _check_ssh_connectivity(cfg: Config) -> list[str]:
 def _check_stack_requirements(
     cfg: Config,
     stacks: list[str],
-) -> tuple[list[tuple[str, str, str]], list[tuple[str, str, str]], list[tuple[str, str, str]]]:
+) -> tuple[
+    list[tuple[str, str, str]],
+    list[tuple[str, str, str]],
+    list[tuple[str, str, str]],
+    list[tuple[str, str, str]],
+]:
     """Check mounts, networks, and devices for all stacks with a progress bar.
 
-    Returns (mount_errors, network_errors, device_errors) where each is a list of
-    (stack, host, missing_item) tuples.
+    Returns (mount_errors, network_errors, device_errors, preflight_errors) where
+    each is a list of (stack, host, item_or_error) tuples.
     """
 
     async def check_stack(
@@ -252,22 +257,23 @@ def _check_stack_requirements(
         list[tuple[str, str, str]],
         list[tuple[str, str, str]],
         list[tuple[str, str, str]],
+        list[tuple[str, str, str]],
     ]:
         """Check requirements for a single stack on all its hosts."""
         host_names = cfg.get_hosts(stack)
         mount_errors: list[tuple[str, str, str]] = []
         network_errors: list[tuple[str, str, str]] = []
         device_errors: list[tuple[str, str, str]] = []
+        preflight_errors: list[tuple[str, str, str]] = []
 
         for host_name in host_names:
-            missing_paths, missing_nets, missing_devs = await check_stack_requirements(
-                cfg, stack, host_name
-            )
-            mount_errors.extend((stack, host_name, p) for p in missing_paths)
-            network_errors.extend((stack, host_name, n) for n in missing_nets)
-            device_errors.extend((stack, host_name, d) for d in missing_devs)
+            preflight = await check_stack_requirements(cfg, stack, host_name)
+            mount_errors.extend((stack, host_name, p) for p in preflight.missing_paths)
+            network_errors.extend((stack, host_name, n) for n in preflight.missing_networks)
+            device_errors.extend((stack, host_name, d) for d in preflight.missing_devices)
+            preflight_errors.extend((stack, host_name, e) for e in preflight.check_errors)
 
-        return stack, mount_errors, network_errors, device_errors
+        return stack, mount_errors, network_errors, device_errors, preflight_errors
 
     results = run_parallel_with_progress(
         "Checking requirements",
@@ -278,12 +284,14 @@ def _check_stack_requirements(
     all_mount_errors: list[tuple[str, str, str]] = []
     all_network_errors: list[tuple[str, str, str]] = []
     all_device_errors: list[tuple[str, str, str]] = []
-    for _, mount_errs, net_errs, dev_errs in results:
+    all_preflight_errors: list[tuple[str, str, str]] = []
+    for _, mount_errs, net_errs, dev_errs, preflight_errs in results:
         all_mount_errors.extend(mount_errs)
         all_network_errors.extend(net_errs)
         all_device_errors.extend(dev_errs)
+        all_preflight_errors.extend(preflight_errs)
 
-    return all_mount_errors, all_network_errors, all_device_errors
+    return all_mount_errors, all_network_errors, all_device_errors, all_preflight_errors
 
 
 def _report_config_status(cfg: Config) -> bool:
@@ -357,6 +365,21 @@ def _report_requirement_errors(errors: list[tuple[str, str, str]], category: str
             console.print(f"    [red]✗[/] {item}")
 
 
+def _report_preflight_check_errors(errors: list[tuple[str, str, str]]) -> None:
+    """Report remote preflight failures grouped by stack."""
+    by_stack: dict[str, list[tuple[str, str]]] = {}
+    for stack, host, error in errors:
+        by_stack.setdefault(stack, []).append((host, error))
+
+    console.print(f"[red]Remote check failures[/] ({len(errors)}):")
+    for stack, items in sorted(by_stack.items()):
+        host = items[0][0]
+        failures = [failure for _, failure in items]
+        console.print(f"  [cyan]{stack}[/] on [magenta]{host}[/]:")
+        for failure in failures:
+            console.print(f"    [red]✗[/] {failure}")
+
+
 def _report_ssh_status(unreachable_hosts: list[str]) -> bool:
     """Report SSH connectivity status. Returns True if there are errors."""
     if unreachable_hosts:
@@ -403,8 +426,13 @@ def _run_remote_checks(cfg: Config, svc_list: list[str], *, show_host_compat: bo
     console.print()  # Spacing before mounts/networks check
 
     # Check mounts, networks, and devices
-    mount_errors, network_errors, device_errors = _check_stack_requirements(cfg, svc_list)
+    mount_errors, network_errors, device_errors, preflight_errors = _check_stack_requirements(
+        cfg, svc_list
+    )
 
+    if preflight_errors:
+        _report_preflight_check_errors(preflight_errors)
+        has_errors = True
     if mount_errors:
         _report_requirement_errors(mount_errors, "mounts")
         has_errors = True
@@ -414,7 +442,7 @@ def _run_remote_checks(cfg: Config, svc_list: list[str], *, show_host_compat: bo
     if device_errors:
         _report_requirement_errors(device_errors, "devices")
         has_errors = True
-    if not mount_errors and not network_errors and not device_errors:
+    if not preflight_errors and not mount_errors and not network_errors and not device_errors:
         print_success("All mounts, networks, and devices exist")
 
     if show_host_compat:
diff --git a/src/compose_farm/console.py b/src/compose_farm/console.py
index d56dc31..a3f8cf6 100644
--- a/src/compose_farm/console.py
+++ b/src/compose_farm/console.py
@@ -41,6 +41,14 @@ class _LazyConsole:
         """Proxy print calls to the underlying Rich console."""
         self._get().print(*args, **kwargs)
 
+    def __enter__(self) -> Console:
+        """Delegate context-manager use to the underlying Rich console."""
+        return self._get().__enter__()
+
+    def __exit__(self, *args: object) -> Any:
+        """Delegate context-manager use to the underlying Rich console."""
+        return self._get().__exit__(*args)
+
     def __getattr__(self, name: str) -> Any:
         return getattr(self._get(), name)
 
diff --git a/src/compose_farm/executor.py b/src/compose_farm/executor.py
index e4f235a..d2f3b35 100644
--- a/src/compose_farm/executor.py
+++ b/src/compose_farm/executor.py
@@ -116,6 +116,7 @@ def build_ssh_command(host: Host, command: str, *, tty: bool = False) -> list[st
     key_path = get_key_path()
     if key_path:
         ssh_args.extend(["-i", str(key_path)])
+        ssh_args.extend(["-o", "IdentitiesOnly=yes"])
 
     if host.port != _DEFAULT_SSH_PORT:
         ssh_args.extend(["-p", str(host.port)])
@@ -166,6 +167,17 @@ class CommandResult:
         return self.exit_code < 0 or self.exit_code == self._SSH_CONNECTION_CLOSED
 
 
+class RemoteCheckError(RuntimeError):
+    """Raised when a remote preflight check could not be executed."""
+
+    def __init__(self, host: str, context: str, detail: str) -> None:
+        """Initialize the error with host, check context, and failure detail."""
+        self.host = host
+        self.context = context
+        self.detail = detail.strip() or "unknown error"
+        super().__init__(f"{context} failed on {host}: {self.detail}")
+
+
 def is_local(host: Host) -> bool:
     """Check if host should run locally (no SSH)."""
     addr = host.address.lower()
@@ -309,7 +321,7 @@ async def _run_ssh_command(
                 )
     except (OSError, asyncssh.Error) as e:
         err_console.print(f"{format_stack_prefix(stack)} [red]SSH error:[/] {e}")
-        return CommandResult(stack=stack, exit_code=1, success=False)
+        return CommandResult(stack=stack, exit_code=1, success=False, stderr=str(e))
 
 
 async def run_command(
@@ -657,6 +669,9 @@ async def _batch_check_existence(
 
     command = "; ".join(checks)
     result = await run_command(host, command, context, stream=False)
+    if not result.success:
+        detail = result.stderr or result.stdout or f"exit code {result.exit_code}"
+        raise RemoteCheckError(host_name, context, detail)
 
     exists: dict[str, bool] = dict.fromkeys(items, False)
     for raw_line in result.stdout.splitlines():
diff --git a/src/compose_farm/operations.py b/src/compose_farm/operations.py
index 46d9ac2..d2d71a8 100644
--- a/src/compose_farm/operations.py
+++ b/src/compose_farm/operations.py
@@ -20,6 +20,7 @@ from .console import (
 )
 from .executor import (
     CommandResult,
+    RemoteCheckError,
     check_networks_exist,
     check_paths_exist,
     check_stack_running,
@@ -49,11 +50,14 @@ class PreflightResult(NamedTuple):
     missing_paths: list[str]
     missing_networks: list[str]
     missing_devices: list[str]
+    check_errors: list[str]
 
     @property
     def ok(self) -> bool:
         """Return True if all checks passed."""
-        return not (self.missing_paths or self.missing_networks or self.missing_devices)
+        return not (
+            self.missing_paths or self.missing_networks or self.missing_devices or self.check_errors
+        )
 
 
 async def _run_compose_step(
@@ -125,26 +129,37 @@ async def check_stack_requirements(
 
     Verifies that all required paths (volumes), networks, and devices exist.
     """
+    check_errors: list[str] = []
+
     # Check mount paths
     paths = get_stack_paths(cfg, stack)
-    path_exists = await check_paths_exist(cfg, host_name, paths)
-    missing_paths = [p for p, found in path_exists.items() if not found]
+    try:
+        path_exists = await check_paths_exist(cfg, host_name, paths)
+        missing_paths = [p for p, found in path_exists.items() if not found]
+    except RemoteCheckError as e:
+        return PreflightResult([], [], [], [str(e)])
 
     # Check external networks
     networks = parse_external_networks(cfg, stack)
     missing_networks: list[str] = []
     if networks:
-        net_exists = await check_networks_exist(cfg, host_name, networks)
-        missing_networks = [n for n, found in net_exists.items() if not found]
+        try:
+            net_exists = await check_networks_exist(cfg, host_name, networks)
+            missing_networks = [n for n, found in net_exists.items() if not found]
+        except RemoteCheckError as e:
+            check_errors.append(str(e))
 
     # Check devices
     devices = parse_devices(cfg, stack)
     missing_devices: list[str] = []
     if devices:
-        dev_exists = await check_paths_exist(cfg, host_name, devices)
-        missing_devices = [d for d, found in dev_exists.items() if not found]
+        try:
+            dev_exists = await check_paths_exist(cfg, host_name, devices)
+            missing_devices = [d for d, found in dev_exists.items() if not found]
+        except RemoteCheckError as e:
+            check_errors.append(str(e))
 
-    return PreflightResult(missing_paths, missing_networks, missing_devices)
+    return PreflightResult(missing_paths, missing_networks, missing_devices, check_errors)
 
 
 async def _cleanup_and_rollback(
@@ -182,6 +197,8 @@ def _report_preflight_failures(
 ) -> None:
     """Report pre-flight check failures."""
     print_error(f"{format_stack_prefix(stack)} Cannot start on [magenta]{target_host}[/]:")
+    for err in preflight.check_errors:
+        print_error(f"  remote check failed: {err}")
     for path in preflight.missing_paths:
         print_error(f"  missing path: {path}")
     for net in preflight.missing_networks:
diff --git a/tests/test_cli_management.py b/tests/test_cli_management.py
new file mode 100644
index 0000000..6ad36cc
--- /dev/null
+++ b/tests/test_cli_management.py
@@ -0,0 +1,37 @@
+"""Tests for CLI management helpers."""
+
+from pathlib import Path
+from unittest.mock import AsyncMock, patch
+
+from compose_farm.cli import management
+from compose_farm.config import Config, Host
+from compose_farm.operations import PreflightResult
+
+
+def test_check_stack_requirements_aggregates_remote_check_errors(tmp_path: Path) -> None:
+    """Cf check should keep remote check failures separate from missing resources."""
+    config = Config(
+        compose_dir=tmp_path,
+        hosts={"host1": Host(address="localhost")},
+        stacks={"svc": "host1"},
+    )
+    preflight = PreflightResult(
+        missing_paths=[],
+        missing_networks=[],
+        missing_devices=[],
+        check_errors=["mount-check failed on host1: Permission denied"],
+    )
+
+    with patch(
+        "compose_farm.cli.management.check_stack_requirements",
+        new_callable=AsyncMock,
+        return_value=preflight,
+    ):
+        mount_errors, network_errors, device_errors, preflight_errors = (
+            management._check_stack_requirements(config, ["svc"])
+        )
+
+    assert mount_errors == []
+    assert network_errors == []
+    assert device_errors == []
+    assert preflight_errors == [("svc", "host1", "mount-check failed on host1: Permission denied")]
diff --git a/tests/test_console.py b/tests/test_console.py
new file mode 100644
index 0000000..b3b5f3a
--- /dev/null
+++ b/tests/test_console.py
@@ -0,0 +1,11 @@
+"""Tests for console helpers."""
+
+from compose_farm.console import _LazyConsole
+
+
+def test_lazy_console_supports_context_manager() -> None:
+    """Rich Progress enters the provided console as a context manager."""
+    console = _LazyConsole()
+
+    with console as rich_console:
+        assert rich_console is not None
diff --git a/tests/test_executor.py b/tests/test_executor.py
index a987423..d192a22 100644
--- a/tests/test_executor.py
+++ b/tests/test_executor.py
@@ -11,8 +11,10 @@ import pytest
 from compose_farm.config import Config, Host
 from compose_farm.executor import (
     CommandResult,
+    RemoteCheckError,
     _run_local_command,
     _stream_output_lines,
+    build_ssh_command,
     check_networks_exist,
     check_paths_exist,
     check_stack_running,
@@ -129,6 +131,24 @@ class TestRunCommand:
         assert result.success is True
 
 
+class TestBuildSshCommand:
+    """Tests for native SSH command construction."""
+
+    def test_uses_only_compose_farm_key_when_present(self, tmp_path: Path) -> None:
+        """Native ssh should match asyncssh by not falling back to agent keys."""
+        key_path = tmp_path / "id_ed25519"
+        host = Host(address="192.168.1.10", user="me")
+
+        with patch("compose_farm.executor.get_key_path", return_value=key_path):
+            args = build_ssh_command(host, "true")
+
+        assert args[0] == "ssh"
+        assert "-i" in args
+        assert str(key_path) in args
+        assert "-o" in args
+        assert "IdentitiesOnly=yes" in args
+
+
 class TestRunCompose:
     """Tests for compose command execution."""
 
@@ -383,6 +403,28 @@ class TestCheckPathsExist:
         result = await check_paths_exist(config, "local", [])
         assert result == {}
 
+    async def test_remote_command_failure_raises(self, tmp_path: Path) -> None:
+        """SSH/preflight failures should not look like every path is missing."""
+        config = Config(
+            compose_dir=tmp_path,
+            hosts={"remote": Host(address="192.168.1.10")},
+            stacks={},
+        )
+        failed = CommandResult(
+            stack="mount-check",
+            exit_code=1,
+            success=False,
+            stderr="Permission denied for user basnijholt",
+        )
+
+        with patch("compose_farm.executor.run_command", new_callable=AsyncMock) as mock_run:
+            mock_run.return_value = failed
+            with pytest.raises(RemoteCheckError) as exc_info:
+                await check_paths_exist(config, "remote", ["/opt/stacks"])
+
+        assert "mount-check failed on remote" in str(exc_info.value)
+        assert "Permission denied" in str(exc_info.value)
+
 
 @linux_only
 class TestCheckNetworksExist:
diff --git a/tests/test_operations.py b/tests/test_operations.py
index 712000e..702ec14 100644
--- a/tests/test_operations.py
+++ b/tests/test_operations.py
@@ -10,11 +10,14 @@ import pytest
 
 from compose_farm.cli import lifecycle
 from compose_farm.config import Config, Host
-from compose_farm.executor import CommandResult
+from compose_farm.executor import CommandResult, RemoteCheckError
 from compose_farm.operations import (
+    PreflightResult,
     _migrate_stack,
+    _report_preflight_failures,
     build_discovery_results,
     build_up_cmd,
+    check_stack_requirements,
 )
 
 
@@ -126,6 +129,52 @@ class TestBuildUpCmd:
         )
 
 
+class TestPreflightRequirements:
+    """Tests for stack preflight checks."""
+
+    async def test_remote_check_error_is_not_reported_as_missing_paths(
+        self, basic_config: Config
+    ) -> None:
+        """A failed SSH check should be distinct from real missing paths."""
+        with patch(
+            "compose_farm.operations.check_paths_exist",
+            side_effect=RemoteCheckError(
+                "host2",
+                "mount-check",
+                "Permission denied for user basnijholt",
+            ),
+        ):
+            result = await check_stack_requirements(basic_config, "test-service", "host2")
+
+        assert result.ok is False
+        assert result.missing_paths == []
+        assert result.missing_networks == []
+        assert result.missing_devices == []
+        assert result.check_errors == [
+            "mount-check failed on host2: Permission denied for user basnijholt"
+        ]
+
+    def test_report_preflight_failures_includes_remote_check_error(
+        self, capsys: pytest.CaptureFixture[str]
+    ) -> None:
+        """User-facing preflight output should show the real remote-check cause."""
+        _report_preflight_failures(
+            "test-service",
+            "host2",
+            PreflightResult(
+                missing_paths=[],
+                missing_networks=[],
+                missing_devices=[],
+                check_errors=["mount-check failed on host2: Permission denied"],
+            ),
+        )
+
+        captured = capsys.readouterr()
+        assert "remote check failed" in captured.err
+        assert "Permission denied" in captured.err
+        assert "missing path" not in captured.err
+
+
 class TestUpdateCommandSequence:
     """Tests for update command sequence."""