diff --git a/medeia_macina/cli_entry.py b/medeia_macina/cli_entry.py
index e34ea03..8dce23d 100644
--- a/medeia_macina/cli_entry.py
+++ b/medeia_macina/cli_entry.py
@@ -12,6 +12,34 @@ from pathlib import Path
 import shlex
 
 
+def _ensure_repo_root_on_sys_path(pkg_file: Optional[Path] = None) -> None:
+    """Ensure the repository root (where top-level modules live) is importable.
+
+    The project currently keeps key modules like `CLI.py` at the repo root.
+    When `mm` is invoked from a different working directory, that repo root is
+    not necessarily on `sys.path`, which breaks `import CLI`.
+
+    We infer the repo root by walking up from this package location and looking
+    for a sibling `CLI.py`.
+
+    `pkg_file` exists for unit tests; production uses this module's `__file__`.
+    """
+    try:
+        pkg_dir = (pkg_file or Path(__file__)).resolve().parent
+    except Exception:
+        return
+
+    for parent in pkg_dir.parents:
+        try:
+            if (parent / "CLI.py").exists():
+                parent_str = str(parent)
+                if parent_str not in sys.path:
+                    sys.path.insert(0, parent_str)
+                return
+        except Exception:
+            continue
+
+
 def _parse_mode_and_strip_args(args: List[str]) -> Tuple[Optional[str], List[str]]:
     """Parse --gui/--cli/--mode flags and return (mode, cleaned_args).
 
@@ -103,6 +131,7 @@ def _import_medeia_entry_module():
     the repository (searching for .egg-link, walking parents, or checking CWD).
     """
     try:
+        _ensure_repo_root_on_sys_path()
         return importlib.import_module("medeia_entry")
     except ImportError:
         # Try to find the project root next to this installed package
@@ -165,6 +194,7 @@ def _run_cli(clean_args: List[str]) -> int:
     else:
         # Try importing the top-level `CLI` module directly (editable/repo mode).
         try:
+            _ensure_repo_root_on_sys_path()
             from CLI import MedeiaCLI as _M  # type: ignore
             MedeiaCLI = _M
         except Exception:
diff --git a/scripts/bootstrap.sh b/scripts/bootstrap.sh
index 0c6030e..b470a6a 100644
--- a/scripts/bootstrap.sh
+++ b/scripts/bootstrap.sh
@@ -553,11 +553,16 @@ VENV="$REPO/.venv"
 # Ensure tools installed into the venv are discoverable to subprocess-based providers
 export PATH="$VENV/bin:$PATH"
 
+# Ensure top-level repo modules (e.g. CLI.py) are importable even when 'mm' is
+# invoked from outside the repo directory.
+export PYTHONPATH="$REPO${PYTHONPATH+:$PYTHONPATH}"
+
 # Debug mode: set MM_DEBUG=1 to print repository, venv, and import diagnostics
 if [ -n "${MM_DEBUG:-}" ]; then
   echo "MM_DEBUG: diagnostics" >&2
   echo "Resolved REPO: $REPO" >&2
   echo "Resolved VENV: $VENV" >&2
+  echo "PYTHONPATH: ${PYTHONPATH:-}" >&2
   echo "VENV exists: $( [ -d "$VENV" ] && echo yes || echo no )" >&2
   echo "Candidates:" >&2
   echo "  VENV/bin/mm: $( [ -x "$VENV/bin/mm" ] && echo yes || echo no )" >&2