diff --git a/omop_alchemy/config.py b/omop_alchemy/config.py
index 1f8f0c9..8839fe0 100644
--- a/omop_alchemy/config.py
+++ b/omop_alchemy/config.py
@@ -86,8 +86,19 @@ def get_cdm_context() -> tuple[OmopAlchemyConfig, ResolvedResource]:
 
     The resource is taken from tools.omop_alchemy.default_resource when set;
     otherwise falls back to the canonical CDM_DB resource name.
+
+    Raises
+    ------
+    RuntimeError
+        If no oa-configurator stack config file exists yet.
     """
-    stack = load_stack_config()
+    try:
+        stack = load_stack_config()
+    except FileNotFoundError as exc:
+        raise RuntimeError(
+            "No omop-alchemy configuration found. "
+            "Run `omop-config configure omop_alchemy` to set it up."
+        ) from exc
     pkg_config = OmopAlchemyConfig.from_stack(stack)
     tool = stack.tools.get(OmopAlchemyConfig.tool_name)
     resource_name = (tool.default_resource if tool else None) or OmopAlchemyConfig.CDM_DB.semantic_name
diff --git a/omop_alchemy/maintenance/cli_backup.py b/omop_alchemy/maintenance/cli_backup.py
index 8adbda6..abb28d5 100644
--- a/omop_alchemy/maintenance/cli_backup.py
+++ b/omop_alchemy/maintenance/cli_backup.py
@@ -83,6 +83,11 @@ def create_database_backup(
             raise RuntimeError(
                 "Database backup failed via `pg_dump`." + (f" {stderr}" if stderr else "")
             ) from exc
+        except FileNotFoundError as exc:
+            raise RuntimeError(
+                f"`pg_dump` executable not found at {tool_path!r}. "
+                "It may have been removed from PATH after being resolved."
+            ) from exc
 
     return BackupResult(
         file_path=str(resolved_output_path),
@@ -123,6 +128,11 @@ def restore_database_backup(
             raise RuntimeError(
                 "Database restore failed." + (f" {stderr}" if stderr else "")
             ) from exc
+        except FileNotFoundError as exc:
+            raise RuntimeError(
+                f"Restore executable not found at {tool_path!r}. "
+                "It may have been removed from PATH after being resolved."
+            ) from exc
 
     return BackupResult(
         file_path=str(resolved_input_path),
diff --git a/tests/test_cli_error_handling.py b/tests/test_cli_error_handling.py
new file mode 100644
index 0000000..0916979
--- /dev/null
+++ b/tests/test_cli_error_handling.py
@@ -0,0 +1,74 @@
+"""Tests for missing-config error handling.
+
+get_cdm_context() converts a missing oa-configurator stack file into a clear
+RuntimeError at the source (config.py), rather than handle_error() pattern-
+matching on the raw FileNotFoundError type. This keeps handle_error's
+FileNotFoundError-shaped catch from also swallowing unrelated missing-file
+errors raised elsewhere inside a command body (e.g. a missing pg_dump binary).
+"""
+
+import pytest
+import typer
+
+from omop_alchemy.config import get_cdm_context
+from omop_alchemy.maintenance._cli_utils import handle_error
+from omop_alchemy.maintenance.ui import console
+
+
+@pytest.fixture(autouse=True)
+def _wide_console():
+    """Rich wraps/truncates Panel text at the console's default 80-column
+    width, which is narrower than this message under pytest's captured,
+    non-tty output. Widen it so assertions can match the full text."""
+    original_width = console.width
+    console.width = 200
+    yield
+    console.width = original_width
+
+
+def _raise_file_not_found():
+    raise FileNotFoundError("Config file not found: /home/cava/.config/omop/config.toml")
+
+
+def test_get_cdm_context_raises_runtime_error_when_config_missing(monkeypatch):
+    monkeypatch.setattr("omop_alchemy.config.load_stack_config", _raise_file_not_found)
+    with pytest.raises(RuntimeError, match="omop-config configure omop_alchemy"):
+        get_cdm_context()
+
+
+def test_get_cdm_context_runtime_error_does_not_leak_raw_path(monkeypatch):
+    """The friendly message should not surface the raw exception text."""
+    monkeypatch.setattr("omop_alchemy.config.load_stack_config", _raise_file_not_found)
+    with pytest.raises(RuntimeError) as exc_info:
+        get_cdm_context()
+    assert "/home/cava/.config/omop/config.toml" not in str(exc_info.value)
+
+
+def test_get_cdm_context_runtime_error_chains_original_exception(monkeypatch):
+    monkeypatch.setattr("omop_alchemy.config.load_stack_config", _raise_file_not_found)
+    with pytest.raises(RuntimeError) as exc_info:
+        get_cdm_context()
+    assert isinstance(exc_info.value.__cause__, FileNotFoundError)
+
+
+def test_handle_error_runtime_error_exits_with_code_1_and_prints_hint(capsys):
+    """The RuntimeError from get_cdm_context is handled cleanly, same as any other."""
+    with pytest.raises(typer.Exit) as exc_info:
+        handle_error(
+            RuntimeError(
+                "No omop-alchemy configuration found. "
+                "Run `omop-config configure omop_alchemy` to set it up."
+            )
+        )
+    assert exc_info.value.exit_code == 1
+    captured = capsys.readouterr()
+    assert "omop-config configure omop_alchemy" in captured.out
+
+
+def test_handle_error_does_not_special_case_file_not_found():
+    """A stray FileNotFoundError from elsewhere in a command body must not be
+    mislabeled as a missing-configuration error — it should propagate as-is."""
+    exc = FileNotFoundError("pg_dump: No such file or directory")
+    with pytest.raises(FileNotFoundError) as exc_info:
+        handle_error(exc)
+    assert exc_info.value is exc