diff --git a/apps/api/internal/app/app_test.go b/apps/api/internal/app/app_test.go
index 40fc6be..e5c391f 100644
--- a/apps/api/internal/app/app_test.go
+++ b/apps/api/internal/app/app_test.go
@@ -2418,6 +2418,9 @@ func TestWebmailSentWritesMaildirSent(t *testing.T) {
 	if !strings.Contains(filepath.ToSlash(rawPath), "/.Sent/cur/") {
 		t.Fatalf("raw_path=%q, want .Sent/cur", rawPath)
 	}
+	if !strings.Contains(filepath.Base(rawPath), maildirFlagSeparator()+"S") {
+		t.Fatalf("sent raw_path missing seen flag: %s", rawPath)
+	}
 	raw, err := os.ReadFile(rawPath)
 	if err != nil {
 		t.Fatal(err)
@@ -2506,6 +2509,9 @@ func TestDraftWritesAndUpdatesMaildirDrafts(t *testing.T) {
 	if !strings.Contains(filepath.ToSlash(rawPath), "/.Drafts/cur/") {
 		t.Fatalf("raw_path=%q, want .Drafts/cur", rawPath)
 	}
+	if !strings.Contains(filepath.Base(rawPath), maildirFlagSeparator()+"S") {
+		t.Fatalf("draft raw_path missing seen flag: %s", rawPath)
+	}
 	oldRawPath := rawPath
 
 	payload["subject"] = "draft two"
diff --git a/apps/api/internal/app/mail_handlers.go b/apps/api/internal/app/mail_handlers.go
index 069b063..f7f5a88 100644
--- a/apps/api/internal/app/mail_handlers.go
+++ b/apps/api/internal/app/mail_handlers.go
@@ -328,6 +328,10 @@ func (a *App) handleMailMessage(w http.ResponseWriter, r *http.Request) {
 		return
 	}
 	if r.URL.Query().Get("markRead") != "0" && !msg.IsRead && userHasPermission(currentUser(r), PermissionMailOrganize) {
+		read := true
+		if err := a.updateMessageMaildirFlags(r.Context(), msg.ID, &read, nil); err != nil {
+			a.log.Warn("failed to update maildir read flag", "message_id", msg.ID, "error", err)
+		}
 		_, _ = a.db.ExecContext(r.Context(), `UPDATE messages SET is_read=1, updated_at=? WHERE id=?`, a.now().UTC().Format(time.RFC3339Nano), msg.ID)
 		msg.IsRead = true
 	}
diff --git a/apps/api/internal/app/maildir_write.go b/apps/api/internal/app/maildir_write.go
index c695e11..c47780c 100644
--- a/apps/api/internal/app/maildir_write.go
+++ b/apps/api/internal/app/maildir_write.go
@@ -120,6 +120,7 @@ func (a *App) writeRawMessageToMaildirFolder(ctx context.Context, messageID, fol
 	filename := maildirFilename(messageID, state.MessageID)
 	tmpPath := filepath.Join(folderBase, "tmp", filename)
 	finalPath := filepath.Join(folderBase, subdir, filename)
+	finalPath = maildirPathWithFlags(finalPath, state.IsRead, state.IsStarred)
 	if err := os.WriteFile(tmpPath, raw, 0o600); err != nil {
 		return err
 	}
@@ -490,15 +491,17 @@ func maildirPathWithFlags(path string, read, starred bool) string {
 	}
 	base := name
 	sep := maildirFlagSeparator()
+	existingFlags := ""
 	if idx := strings.LastIndex(base, sep); idx >= 0 {
+		existingFlags = base[idx+len(sep):]
 		base = base[:idx]
 	}
-	flags := ""
+	flags := preserveMaildirFlags(existingFlags, "SF")
 	if read {
-		flags += "S"
+		flags = appendMaildirFlag(flags, 'S')
 	}
 	if starred {
-		flags += "F"
+		flags = appendMaildirFlag(flags, 'F')
 	}
 	if flags != "" {
 		base += sep + flags
@@ -506,6 +509,24 @@ func maildirPathWithFlags(path string, read, starred bool) string {
 	return filepath.Join(dir, base)
 }
 
+func preserveMaildirFlags(flags, managed string) string {
+	var b strings.Builder
+	for _, flag := range flags {
+		if strings.ContainsRune(managed, flag) || strings.ContainsRune(b.String(), flag) {
+			continue
+		}
+		b.WriteRune(flag)
+	}
+	return b.String()
+}
+
+func appendMaildirFlag(flags string, flag rune) string {
+	if strings.ContainsRune(flags, flag) {
+		return flags
+	}
+	return flags + string(flag)
+}
+
 func maildirFlagSeparator() string {
 	if runtime.GOOS == "windows" {
 		return "!2,"