diff --git a/cmd/bd/staleness.go b/cmd/bd/staleness.go
index 934d2224..5db36691 100644
--- a/cmd/bd/staleness.go
+++ b/cmd/bd/staleness.go
@@ -33,7 +33,8 @@ func ensureDatabaseFresh(ctx context.Context) error {
 	if err != nil {
 		// If we can't determine staleness, allow operation to proceed
 		// (better to show potentially stale data than block user)
-		fmt.Fprintf(os.Stderr, "Warning: could not check database staleness: %v\n", err)
+		fmt.Fprintf(os.Stderr, "Warning: Could not verify database freshness: %v\n", err)
+		fmt.Fprintf(os.Stderr, "Proceeding anyway. Data may be stale.\n\n")
 		return nil
 	}
 
diff --git a/internal/autoimport/autoimport.go b/internal/autoimport/autoimport.go
index 15d7d389..7d74b71b 100644
--- a/internal/autoimport/autoimport.go
+++ b/internal/autoimport/autoimport.go
@@ -262,10 +262,16 @@ func CheckStaleness(ctx context.Context, store storage.Storage, dbPath string) (
 		return false, nil
 	}
 
+	// Empty string means no metadata was set (memory store behavior)
+	if lastImportStr == "" {
+		// No metadata yet - expected for first run
+		return false, nil
+	}
+
 	lastImportTime, err := time.Parse(time.RFC3339, lastImportStr)
 	if err != nil {
-		// Corrupted metadata - not critical, assume not stale
-		return false, nil
+		// Corrupted metadata - this is abnormal and should be reported
+		return false, fmt.Errorf("corrupted last_import_time in metadata (cannot parse as RFC3339): %w", err)
 	}
 
 	// Find JSONL using database directory
diff --git a/internal/autoimport/autoimport_test.go b/internal/autoimport/autoimport_test.go
index fefa2f43..70d02964 100644
--- a/internal/autoimport/autoimport_test.go
+++ b/internal/autoimport/autoimport_test.go
@@ -343,6 +343,30 @@ func TestCheckStaleness_NewerJSONL(t *testing.T) {
 	}
 }
 
+func TestCheckStaleness_CorruptedMetadata(t *testing.T) {
+	store := memory.New("")
+	ctx := context.Background()
+
+	tmpDir, err := os.MkdirTemp("", "bd-stale-test-*")
+	if err != nil {
+		t.Fatal(err)
+	}
+	defer os.RemoveAll(tmpDir)
+
+	dbPath := filepath.Join(tmpDir, "bd.db")
+
+	// Set invalid timestamp format
+	store.SetMetadata(ctx, "last_import_time", "not-a-valid-timestamp")
+
+	_, err = CheckStaleness(ctx, store, dbPath)
+	if err == nil {
+		t.Error("Expected error for corrupted metadata, got nil")
+	}
+	if err != nil && !strings.Contains(err.Error(), "corrupted last_import_time") {
+		t.Errorf("Expected 'corrupted last_import_time' error, got: %v", err)
+	}
+}
+
 func TestCheckForMergeConflicts(t *testing.T) {
 	tests := []struct {
 		name      string