diff --git a/internal/smtp/user.go b/internal/smtp/user.go
index ff905866..ae14f30f 100644
--- a/internal/smtp/user.go
+++ b/internal/smtp/user.go
@@ -290,6 +290,9 @@ func (su *smtpUser) Send(from string, to []string, messageReader io.Reader) (err
 		}
 
 		sendPreferences, err := su.getSendPreferences(email, message.MIMEType, mailSettings)
+		if !sendPreferences.Encrypt {
+			containsUnencryptedRecipients = true
+		}
 		if err != nil {
 			return err
 		}