Preflight report output filenames

internal/app/generation_test.go

@@ -6,6 +6,7 @@ import (
 	"errors"
 	"os"
 	"path/filepath"
+	"strings"
 	"sync"
 	"testing"
 	"time"
@@ -276,6 +277,26 @@ func TestGenerateDetailedRejectsConfiguredNonDirectoryBeforeWork(t *testing.T) {
 	}
 }
 
+func TestGenerateDetailedRejectsOverlongOutputBeforeWork(t *testing.T) {
+	missingDirectory := filepath.Join(t.TempDir(), "missing")
+	outputPath := filepath.Join(missingDirectory, strings.Repeat("a", 253)+".md")
+	bundle := generationBundle(t)
+	collector := &generationCollector{bundle: &bundle}
+	executor := &generationExecutor{}
+
+	result, err := GenerateDetailed(context.Background(), GenerateRequest{
+		Config: generationConfig(), Report: ReportDaily,
+		Date: generationTime("2026-05-29T12:00:00-05:00"), Now: generationTime("2026-05-29T08:30:00-05:00"),
+		WorkingDir: t.TempDir(), OutputPath: outputPath, Collector: collector, Executor: executor,
+	})
+	if err == nil || result == nil || collector.called || executor.promptInspections != 0 || executor.called {
+		t.Fatalf("GenerateDetailed() result/error/collector/executor = %#v/%v/%t/%#v", result, err, collector.called, executor)
+	}
+	if _, statErr := os.Stat(missingDirectory); !os.IsNotExist(statErr) {
+		t.Fatalf("missing output directory exists after preflight failure: %v", statErr)
+	}
+}
+
 func TestGenerateDetailedReturnsResolvedResultWhenCollectionFails(t *testing.T) {
 	cfg := config.Defaults()
 	cfg.WeatherAPI.Timezone, cfg.Location.ID = "America/Chicago", "home"