diff --git a/src/Core/GlobalSettings.cs b/src/Core/GlobalSettings.cs
index 892ca9ffad..6cfb0e4e6d 100644
--- a/src/Core/GlobalSettings.cs
+++ b/src/Core/GlobalSettings.cs
@@ -116,6 +116,7 @@ namespace Bit.Core
             {
                 public string Host { get; set; }
                 public int Port { get; set; } = 25;
+                public bool StartTls { get; set; } = false;
                 public bool Ssl { get; set; } = false;
                 public bool SslOverride { get; set; } = false;
                 public string Username { get; set; }
diff --git a/src/Core/Services/Implementations/MailKitSmtpMailDeliveryService.cs b/src/Core/Services/Implementations/MailKitSmtpMailDeliveryService.cs
index b3436e388a..4ef2d86709 100644
--- a/src/Core/Services/Implementations/MailKitSmtpMailDeliveryService.cs
+++ b/src/Core/Services/Implementations/MailKitSmtpMailDeliveryService.cs
@@ -67,7 +67,8 @@ namespace Bit.Core.Services
                     client.ServerCertificateValidationCallback = (s, c, h, e) => true;
                 }
 
-                if(!_globalSettings.Mail.Smtp.Ssl && _globalSettings.Mail.Smtp.Port == 25)
+                if(!_globalSettings.Mail.Smtp.StartTls && !_globalSettings.Mail.Smtp.Ssl &&
+                    _globalSettings.Mail.Smtp.Port == 25)
                 {
                     await client.ConnectAsync(_globalSettings.Mail.Smtp.Host, _globalSettings.Mail.Smtp.Port,
                         MailKit.Security.SecureSocketOptions.None);