From 9444bab05fb3cf9c80db3b7c2f03ced21262eb65 Mon Sep 17 00:00:00 2001
From: Cipher Vance <hello@ciphervance.com>
Date: Sat, 15 Nov 2025 18:43:51 -0600
Subject: [PATCH] add support for better ssl/tls handling

---
 internal/email/email.go | 13 +++++++++++--
 1 file changed, 11 insertions(+), 2 deletions(-)

diff --git a/internal/email/email.go b/internal/email/email.go
index 5305330..9f550f5 100644
--- a/internal/email/email.go
+++ b/internal/email/email.go
@@ -50,14 +50,23 @@ func SendUpdate(subject, body string) (string, error) {
 func send(subject, body, recipient string) bool {
 	cfg := config.Current
 
-	client, err := mail.NewClient(
-		cfg.SMTPServer,
+	var opts []mail.ClientOption
+	opts = append(opts,
 		mail.WithPort(cfg.SMTPPort),
 		mail.WithSMTPAuth(mail.SMTPAuthPlain),
 		mail.WithUsername(cfg.SMTPUser),
 		mail.WithPassword(cfg.SMTPPassword),
 		mail.WithTimeout(10*time.Second),
 	)
+
+	// Use SSL for port 465, STARTTLS for others
+	if cfg.SMTPPort == 465 {
+		opts = append(opts, mail.WithSSL())
+	} else {
+		opts = append(opts, mail.WithTLSPolicy(mail.TLSMandatory))
+	}
+
+	client, err := mail.NewClient(cfg.SMTPServer, opts...)
 	if err != nil {
 		log.Printf("Failed to create mail client: %v", err)
 		return false