diff --git a/internal/wslstate/command.go b/internal/wslstate/command.go
index 6cdcf7d..609f256 100644
--- a/internal/wslstate/command.go
+++ b/internal/wslstate/command.go
@@ -12,6 +12,7 @@ import (
 	"os"
 	"sort"
 	"strings"
+	"syscall"
 
 	"github.com/AviBackToBlack/container-bin/internal/hostenv"
 	"github.com/AviBackToBlack/container-bin/internal/policy"
@@ -367,6 +368,9 @@ func inspectProjectPath(recorded string, lstat func(string) (os.FileInfo, error)
 		}
 		return "MANAGED", nil
 	}
+	if errors.Is(err, syscall.ENOTDIR) {
+		return "UNSAFE", nil
+	}
 	if !errors.Is(err, fs.ErrNotExist) {
 		return "", fmt.Errorf("inspect recorded native WSL project path %s: %w", recorded, err)
 	}
diff --git a/internal/wslstate/command_test.go b/internal/wslstate/command_test.go
index 8343947..233055c 100644
--- a/internal/wslstate/command_test.go
+++ b/internal/wslstate/command_test.go
@@ -7,6 +7,7 @@ import (
 	"io/fs"
 	"os"
 	"strings"
+	"syscall"
 	"testing"
 	"time"
 
@@ -195,6 +196,18 @@ func TestMissingProjectWithUnsafeBoundaryProofIsNeverOrphaned(t *testing.T) {
 	}
 }
 
+func TestProjectPathWithNonDirectoryAncestorIsUnsafe(t *testing.T) {
+	status, err := inspectProjectPath("/work/file/gone", func(string) (os.FileInfo, error) {
+		return nil, &os.PathError{Op: "lstat", Path: "/work/file/gone", Err: syscall.ENOTDIR}
+	}, func(string) error {
+		t.Fatal("boundary proof ran after a non-directory ancestor was already proven")
+		return nil
+	})
+	if err != nil || status != "UNSAFE" {
+		t.Fatalf("non-directory ancestor classification = (%q, %v)", status, err)
+	}
+}
+
 func TestGCRechecksOrphanImmediatelyBeforeRemoval(t *testing.T) {
 	deps, scope := testDependencies(t)
 	orphan, _ := scope.Project("node24", "modules", "/work/restored")