diff --git a/agent/tools/email.py b/agent/tools/email.py
index 45fd355ff1..14a6eb241d 100644
--- a/agent/tools/email.py
+++ b/agent/tools/email.py
@@ -19,6 +19,7 @@ from abc import ABC
 import json
 import smtplib
 import logging
+import ssl
 from email.mime.text import MIMEText
 from email.mime.multipart import MIMEMultipart
 from email.header import Header
@@ -116,11 +117,17 @@ class Email(ToolBase, ABC):
                 if self.check_if_canceled("Email processing"):
                     return
 
-                context = smtplib.ssl.create_default_context()
-                with smtplib.SMTP(self._param.smtp_server, self._param.smtp_port) as server:
-                    server.ehlo()
-                    server.starttls(context=context)
+                context = ssl.create_default_context()
+                if int(self._param.smtp_port) == 465:
+                    server = smtplib.SMTP_SSL(self._param.smtp_server, self._param.smtp_port, timeout=10, context=context)
+                else:
+                    server = smtplib.SMTP(self._param.smtp_server, self._param.smtp_port, timeout=10)
+
+                with server:
                     server.ehlo()
+                    if int(self._param.smtp_port) != 465:
+                        server.starttls(context=context)
+                        server.ehlo()
 
                     # Login
                     smtp_username = self._param.smtp_username or self._param.email
diff --git a/api/utils/web_utils.py b/api/utils/web_utils.py
index d561e944d1..c0ab4b00d7 100644
--- a/api/utils/web_utils.py
+++ b/api/utils/web_utils.py
@@ -162,7 +162,8 @@ async def send_email_html(to_email: str, subject: str, template_key: str, **cont
     smtp = aiosmtplib.SMTP(
         hostname=settings.MAIL_SERVER,
         port=settings.MAIL_PORT,
-        use_tls=True,
+        use_tls=settings.MAIL_USE_SSL,
+        start_tls=settings.MAIL_USE_TLS,
         timeout=10,
     )