Based on feedback we changed the default port back to 587 and added an encryption setting

Thanks @caesay :)

Author: niemyjski

src/Exceptionless.Api/Web.config

@@ -22,12 +22,15 @@
     <!-- Controls whether daily summary emails are sent -->
     <add key="EnableDailySummary" value="false" />
 
-    <!-- Email Client Settings (Uncomment the section below to configure email settings) -->
     <!--
-    <add key="SmtpHost" value="localhost" />
-    <add key="SmtpPort" value="25" />
-    <add key="SmtpEnableSSL" value="false" />
-    <add key="SmtpUser" value="" />
+      Email Client Settings (Uncomment the section below to change the default email settings)
+      There are three valid SmtpEncryption settings: None, SSL and StartTLS
+    -->
+    <!--
+    <add key="SmtpHost" value="domain.com" />
+    <add key="SmtpPort" value="587" />
+    <add key="SmtpEncryption" value="StartTLS" />
+    <add key="SmtpUser" value="user@domain.com" />
     <add key="SmtpPassword" value="" />
     -->
 

src/Exceptionless.Core/Settings.cs

@@ -140,7 +140,7 @@ public class Settings : SettingsBase<Settings> {
 
         public int SmtpPort { get; private set; }
 
-        public bool SmtpEnableSSL { get; private set; }
+        public SmtpEncryption SmtpEncryption { get; private set; }
 
         public string SmtpUser { get; private set; }
 
@@ -203,8 +203,8 @@ public override void Initialize() {
             TestEmailAddress = GetString(nameof(TestEmailAddress), "noreply@exceptionless.io");
             SmtpFrom = GetString(nameof(SmtpFrom), "Exceptionless <noreply@exceptionless.io>");
             SmtpHost = GetString(nameof(SmtpHost), "localhost");
-            SmtpPort = GetInt(nameof(SmtpPort), String.Equals(SmtpHost, "localhost") ? 25 : 465);
-            SmtpEnableSSL = GetBool(nameof(SmtpEnableSSL), !String.Equals(SmtpHost, "localhost"));
+            SmtpPort = GetInt(nameof(SmtpPort), String.Equals(SmtpHost, "localhost") ? 25 : 587);
+            SmtpEncryption = GetEnum<SmtpEncryption>(nameof(SmtpEncryption), GetDefaultSmtpEncryption(SmtpPort));
             SmtpUser = GetString(nameof(SmtpUser));
             SmtpPassword = GetString(nameof(SmtpPassword));
 
@@ -232,8 +232,21 @@ public override void Initialize() {
             Version = FileVersionInfo.GetVersionInfo(typeof(Settings).Assembly.Location).ProductVersion;
         }
 
+        private SmtpEncryption GetDefaultSmtpEncryption(int port) {
+            switch (port) {
+                case 465:
+                    return SmtpEncryption.SSL;
+                case 587:
+                case 2525:
+                    return SmtpEncryption.StartTLS;
+                default:
+                    return SmtpEncryption.None;
+            }
+        }
+
         public const string JobBootstrappedServiceProvider = "Exceptionless.Insulation.Jobs.JobBootstrappedServiceProvider,Exceptionless.Insulation";
 
+
         public LoggerFactory GetLoggerFactory() {
             return new LoggerFactory();
         }
@@ -244,4 +257,10 @@ public enum WebsiteMode {
         QA,
         Dev
     }
-}
+
+    public enum SmtpEncryption {
+        None,
+        StartTLS,
+        SSL
+    }
+}

src/Exceptionless.Insulation/Mail/MailKitMailSender.cs

@@ -6,15 +6,12 @@
 using Exceptionless.Core.Mail;
 using Foundatio.Utility;
 using MailKit.Net.Smtp;
+using MailKit.Security;
 using MimeKit;
 using MailMessage = Exceptionless.Core.Queues.Models.MailMessage;
 
 namespace Exceptionless.Insulation.Mail {
     public class MailKitMailSender : IMailSender {
-        private long _totalSent;
-
-        public long TotalSent => _totalSent;
-
         public async Task SendAsync(MailMessage model) {
             var message = CreateMailMessage(model);
             message.Headers.Add("X-Mailer-Machine", Environment.MachineName);
@@ -25,7 +22,7 @@ public async Task SendAsync(MailMessage model) {
             using (var client = new SmtpClient()) {
                 client.ServerCertificateValidationCallback = (s, c, h, e) => true;
 
-                await client.ConnectAsync(Settings.Current.SmtpHost, Settings.Current.SmtpPort, Settings.Current.SmtpEnableSSL).AnyContext();
+                await client.ConnectAsync(Settings.Current.SmtpHost, Settings.Current.SmtpPort, GetSecureSocketOption(Settings.Current.SmtpEncryption)).AnyContext();
 
                 // Note: since we don't have an OAuth2 token, disable the XOAUTH2 authentication mechanism.
                 client.AuthenticationMechanisms.Remove("XOAUTH2");
@@ -34,13 +31,21 @@ public async Task SendAsync(MailMessage model) {
                     await client.AuthenticateAsync(Settings.Current.SmtpUser, Settings.Current.SmtpPassword).AnyContext();
 
                 await client.SendAsync(message).AnyContext();
-
-                // we don't care if there is an error at this point.
-                Interlocked.Increment(ref _totalSent);
                 await client.DisconnectAsync(true).AnyContext();
             }
         }
 
+        private SecureSocketOptions GetSecureSocketOption(SmtpEncryption encryption) {
+            switch (encryption) {
+                case SmtpEncryption.StartTLS:
+                    return SecureSocketOptions.StartTls;
+                case SmtpEncryption.SSL:
+                    return SecureSocketOptions.SslOnConnect;
+                default:
+                    return SecureSocketOptions.Auto;
+            }
+        }
+
         private MimeMessage CreateMailMessage(MailMessage notification) {
             var message = new MimeMessage { Subject = notification.Subject };
             var builder = new BodyBuilder();

src/Jobs/App.config

@@ -19,12 +19,15 @@
     <!-- Controls whether daily summary emails are sent -->
     <add key="EnableDailySummary" value="false" />
 
-    <!-- Email Client Settings (Uncomment the section below to configure email settings) -->
     <!--
-    <add key="SmtpHost" value="localhost" />
-    <add key="SmtpPort" value="25" />
-    <add key="SmtpEnableSSL" value="false" />
-    <add key="SmtpUser" value="" />
+      Email Client Settings (Uncomment the section below to change the default email settings)
+      There are three valid SmtpEncryption settings: None, SSL and StartTLS
+    -->
+    <!--
+    <add key="SmtpHost" value="domain.com" />
+    <add key="SmtpPort" value="587" />
+    <add key="SmtpEncryption" value="StartTLS" />
+    <add key="SmtpUser" value="user@domain.com" />
     <add key="SmtpPassword" value="" />
     -->