Getting started with SMTP component

• Introduction
• Feature map as compared with System.Net.Mail.SmtpClient
• Import namespaces and set license key
• Send e-mail in a single line of code
• Send e-mail to SMTP relay server
• Send HTML e-mail with attachment
• Send e-mail with Reply-To and multiple To, CC and BCC recipients
• Send if server requires SMTP authentication
• Send if server requires SSL
• Send to e-mail address with international domain (IDN)
• Send e-mail directly without SMTP relay server
• Verify e-mail address without sending actual e-mail
• Exceptions and errors
• MS Exchange SMTP issues
• Log file of SMTP conversation
• Troubleshoot common sending errors and non-delivery

Introduction

To create and send e-mails, you can use MailBee.NET SMTP component. That's how it happens:

• You set the message properties like To/From/Subject headers and the body text, add attachments, etc.
• SMTP component creates MIME representation of the e-mail. MIME (RFC2822) is the standard format for e-mail interchange in the Internet and between applications.
• SMTP component sends the MIME data to your relay server using SMTP data transfer protocol. The relay server then should deliver the message to its intended recipients.

There are lots of other options, however. Just to name a few:

• Load the message to be sent from another source (like an XML file or memory).
• Use the classes of MIME component to build complex e-mails.
• Use mail merge over database to produce and send a series of e-mails based on a common template.
• Submit the resulting e-mail to an e-mail pickup service for background delivery, or send directly to intended recipients without an SMTP relay server.
• Upload the e-mail to an IMAP server, save it into a file or memory (not using SMTP component at all).

In the diagram below, you can find what you can feed to MailBee.NET classes on input and which options you have in order to save or send the resulting e-mail.

You can also enable various options and apply a number of transformations to the message being composed. For instance:

• Automatically attach images referenced in the HTML body and generate its plain-text version.
• Sign the message with DKIM and DomainKeys.
• Encrypt and sign the message with S/MIME.
• Request the delivery confirmation.

Now, let's assume the message has been composed and you're about to send it through your SMTP relay server (the most common scenario). A few tips here:

• You can track the operation progress with events.
• You can enable logging SMTP session into a file for troubleshooting or other purposes.
• You may need to unblock SMTP port on MailBee.NET machine or use alternate port (for instance, port 25 is often blocked while port 587 is not and many SMTP servers listen to that port as well).
• For SMTP servers which require authentication or SSL connection, you can enable any of these options.

Once the message has been successfully sent to the SMTP server, MailBee.NET's job is over. This, however, does not guarantee the intended recipient has received the message. The recipient's server may seem to accept the message but then bounce it back, put it into Spam folder or just delete it silently. You can learn more in Troubleshoot common sending errors and non-delivery section if you face such issues.

Feature map as compared with System.Net.Mail.SmtpClient

.NET Framework provides System.Net.Mail classes which can be used to send e-mails to SMTP servers.

The below are comparison tables of MailBee.NET and System.Net.Mail features related to creating and sending e-mails. They also provide quick access to the documentation on all the features.

With regard to creating e-mails, MailBee.NET provides more features such as automatic importing of embedded pictures in HTML content, security facilities like S/MIME and DKIM, mail merge.

Besides that, MailBee.NET gives you much more control how e-mails are generated, how SMTP connection is established, how to react if certain recipients were rejected by the server, and so on.

With MailBee.NET events, you can not only monitor the operation progress (being a passive observer), but also actively interfere into the execution. For instance, you can alter the message which is about to be sent, or cancel sending a particular message in mail merge series, and so on.

MailBee.NET exception model is far more developed in comparison to System.Net.Mail so that you can programmatically respond to many specific errors accordingly their nature. For instance, it's not easily possible to distinguish between "bad login or password" and "bad sender's e-mail address" errors with System.Net.Mail while MailBee.NET provides separate exceptions for them.

However, whether to use MailBee.NET or System.Net.Mail is not "either-or" question. MailBee.NET can work together with System.Net.Mail to let you make the transition process smoother.

For instance, you can export System.Net.Mail.MailMessage into MailBee.Mime.MailMessage and then send the resulting e-mail with MailBee.NET SMTP component. The rest of your code which composes e-mails with the help of System.Net.Mail remains intact. See Send e-mail created from System.Net.Mail.MailMessage topic for details.

The opposite scenario (export MailBee.Mime.MailMessage into System.Net.Mail.MailMessage) is also supported.

Import namespaces and set license key

Reference MailBee.NET.dll

To start using MailBee.NET in your projects, add MailBee.NET Objects reference to your project. You can use NuGet Packager Manager console for that:

Install-Package MailBee.NET

If NuGet is not an option (for instance, you have older version of Visual Studio), see below.

In Project menu, click Add a reference:

Then, under .NET tab, locate MailBee.NET Objects. If you installed multiple versions of MailBee.NET Objects, select v2.0 in Runtime column if you're using .NET 2.0/3.5. If you're using .NET v4.5 or higher, select v4.0 Runtime:

In newer versions of Visual Studio, Runtime column is not there and path to the dll is not shown by default so you may need to hover mouse cursor over to see the path (and determine the version). In this case, it's .NET 4.5 version of MailBee.NET.dll:

Click OK to add the reference to your project. MailBee.NET entry should appear in References list of your project.

Import MailBee.NET namespaces

Now, import MailBee.NET namespaces to the beginning of your source code files where you'll use MailBee.NET.

When creating and sending e-mails, you'll typically need some of these namespaces:

using MailBee;
using MailBee.Mime;
using MailBee.Security;
using MailBee.SmtpMail;

Imports MailBee
Imports MailBee.Mime
Imports MailBee.Security
Imports MailBee.SmtpMail

If you're using direct send mode (without an SMTP relay server) or your code interoperates with Imap or Pop3 components, you may also need to import these namespaces as well:

using MailBee.DnsMX;
using MailBee.Pop3Mail;
using MailBee.ImapMail;

Imports MailBee.DnsMX
Imports MailBee.Pop3Mail
Imports MailBee.ImapMail

Obtain license key

Now, you need to specify your trial or permanent MailBee.NET license key to unlock the product. If you do not yet have a key, you can generate the trial key with "Get a Trial Key" utility (available in Programs / MailBee.NET Objects menu).

You can specify the key in a number of ways (Windows registry, app.config or web.config file, directly in the code). This guide shows two methods of that: hard-coded key and key stored in app.config (web.config for ASP.NET).

Using Windows registry is not recommended as your application may be lacking permission to access the required registry branches. If you still need to use the registry (e.g. if your application is distributed with the source code so that you cannot embed the key there), refer to Using License Keys topic in MailBee.NET Objects documentation for details.

Option A - specify license key directly in code

Before the first use and creating any instances of Smtp class, set the static MailBee.Global.LicenseKey property to assign the license key. It's assumed you've already imported MailBee.SmtpMail namespace with using (C#) or Imports (VB) directives.

MailBee.Global.LicenseKey = "MN100-0123456789ABCDEF-0123";

MailBee.Global.LicenseKey = "MN100-0123456789ABCDEF-0123"

You can also create and unlock instances of Smtp class, passing the license key as a parameter of Smtp(string) constructor. Again, it's assumed you've already imported MailBee.SmtpMail namespace.

Smtp mailer = new Smtp("MN100-0123456789ABCDEF-0123");

Dim mailer As New Smtp("MN100-0123456789ABCDEF-0123")

Option B - put license key in app.config or web.config

Alternatively, you can add app.config to your project (if you do not already have it there) and specify MailBee.NET SMTP license key there.

For ASP.NET application, web.config is always available so that you can immediately edit it, but for other application types you may have to add app.config manually.

The below we are using Visual Studio 2008 but it's all the same with newer Visual Studio versions as well. For instance, we are using Visual Studio 2010 in similar topic in IMAP and POP3 guide.

In Projects menu, click Add New Item:

Select Application Configuration File and click Add:

In app.config or web.config, locate <appSettings> entry in <configuration> section (if it's not there, create it), and add MailBee.NET license key as follows:

<?xml version="1.0" encoding="utf-8" ?>
  <configuration>
    <appSettings>
      <add key="MailBee.Global.LicenseKey" value="MN100-0123456789ABCDEF-0123"/>
  </appSettings>
</configuration>

Note that <appSettings> may also appear as <applicationSettings> in your case.

If <appSettings> originally looked as <appSettings/> (self-closing tag syntax), you'll need to unfold it to <appSettings></appSettings> so that you could insert <add key .../> there.

You can also specify the key in machine.config file. This will enable access to the license key to all applications on the computer so that there will be no need to specify the license key in each application separately. For instance, this is the preferred way if you a hosting provider willing to let your hosting clients create and run applications which use MailBee.NET without disclosing your license key to them.

Send e-mail in a single line of code

We'll send a simple plain-text e-mail using the static (Shared in VB) Smtp.QuickSend method. No need to create an instance of Smtp class for that:

Smtp.QuickSend("john@domain.com", "jane@company.com", "Question", "How are you?");

Smtp.QuickSend("john@domain.com", "jane@company.com", "Question", "How are you?")

Here and below, we assume that MailBee.SmtpMail namespace is already imported and MailBee.Global.LicenseKey is specified (in the code or in app.config or web.config file).

E-mail addresses can contain display names, and you can specify multiple recipients (comma-separated):

Smtp.QuickSend("John Doe <john@domain.com>",
    "Jane Doe <jane@company.com>, noname@example.com", "Question", "How are you?");

Smtp.QuickSend("John Doe <john@domain.com>", _
    "Jane Doe <jane@company.com>, noname@example.com", "Question", "How are you?"

Other overloads of Smtp.QuickSend method allow you to send HTML e-mails with attachments or user-supplied MailMessage objects, all with a single line of code.

If Smtp.QuickSend method fails, it throws MailBeeException which you can catch and analyze in your code. If the method succeeds, this means the message has reached the end recipient's server.

Smtp.QuickSend sends e-mails via DNS MX lookup, not using any SMTP relay server (so-called "direct send" mode). This mode has some limitations described in Send e-mail directly without SMTP relay server topic. Also, because no instance of Smtp object is created, you cannot configure anything or check the log file in case if trouble-shooting needed, etc.

Send e-mail to SMTP relay server

Now let's create an instance of Smtp class and send a simple plain-text e-mail via an SMTP relay server:

Smtp mailer = new Smtp();
mailer.SmtpServers.Add("mail.here.com");
mailer.From.AsString = "John Doe <john.doe@here.com>";
mailer.To.AsString = "Jane Doe <jane.doe@there.com>";
mailer.Subject = "Meeting request";
mailer.BodyPlainText = "Can we meet today?";
mailer.Send();

Dim mailer As Smtp = New Smtp()
mailer.SmtpServers.Add("mail.here.com")
mailer.From.AsString = "John Doe <john.doe@here.com>"
mailer.To.AsString = "Jane Doe <jane.doe@there.com>"
mailer.Subject = "Meeting request"
mailer.BodyPlainText = "Can we meet today?"
mailer.Send()

mail.here.com is the host name of your SMTP relay server.

No SMTP authentication is used in this sample (anonymous mode). See Send if server requires SMTP authentication topic on how to enable authentication if required.

If Smtp.Send method still throws an exception, you may need to fine-tune SMTP authentication, enable SSL, or open SMTP ports in the firewall. See Send if server requires SSL (like Gmail), MS Exchange SMTP issues or Troubleshoot common sending errors and non-delivery topics for details.

Send HTML e-mail with attachment

This sample sends an HTML e-mail with attachment (MailBee.NET will also auto-generate the plain-text version of the supplied HTML). The e-mail is sent through an SMTP relay server without authentication:

Smtp mailer = new Smtp();
mailer.SmtpServers.Add("mail.here.com");
mailer.From.AsString = "John Doe <john.doe@here.com>";
mailer.To.AsString = "Jane Doe <jane.doe@there.com>";
mailer.Subject = "Meeting request";
mailer.BodyHtmlText = "<html><body>Can we meet today?</body></html>";
mailer.AddAttachment(@"C:\Temp\details.doc");
mailer.Send();

Dim mailer As Smtp = New Smtp()
mailer.SmtpServers.Add("mail.here.com")
mailer.From.AsString = "John Doe <john.doe@here.com>"
mailer.To.AsString = "Jane Doe <jane.doe@there.com>"
mailer.Subject = "Meeting request"
mailer.BodyHtmlText = "<html><body>Can we meet today?</body></html>"
mailer.AddAttachment("C:\Temp\details.doc")
mailer.Send()

If you need more advanced features or control over building HTML e-mails or attaching files, see Compose complex e-mail with multiple parts and attachments guide.

Send e-mail with Reply-To and multiple To, CC and BCC recipients

Smtp object itself provides a very limited set of e-mail message properties, and Reply-To, CC or BCC headers are not available there. This is because Smtp object is for sending e-mails, not for creating them. The object responsible for creating e-mails is MailMessage of MailBee.Mime namespace. It assembles the message properties into the MIME data which can then be transmitted to the SMTP server.

Smtp object has Smtp.Message property which references the MailMessage object to be sent. For instance, Smtp.Subject is just a shorter form of Smtp.Message.Subject, and Smtp.AddAttachment is a shorter form of Smtp.Message.Attachments.Add.

The code below demonstrates how to set From, Reply-To, To, CC, BCC in different ways:

Smtp mailer = new Smtp();
mailer.SmtpServers.Add("mail.here.com");

// Set From address as a single string.
mailer.Message.From.AsString = "John Doe <john.doe@here.com>";

// Add 1st Reply-To address.
mailer.Message.ReplyTo.AddFromString("John Doe <jdoe@here.com>");

// Add 2nd Reply-To address (no display name).
mailer.Message.ReplyTo.Add("noname@here.com");

// Specify "To" as a single string containing 2 e-mail addresses.
mailer.Message.To.AsString = "Jane Doe <jane.doe@there.com>, Alice <alice@there.com>";

 // Add 3rd and 4th "To" addresses.
mailer.Message.To.AddFromString("mike@nodisplayname.com, Liz <liz@somewhere.com>");

// Specify 2 "CC" addresses separately, with different syntax.
mailer.Message.Cc.AddFromString("Bob Smith <bob@example.com>");
mailer.Message.Cc.Add("john.doe@here.com", "John Doe");

// Specify BCC (no need to supply display name as BCC header will be removed anyway).
mailer.Message.Bcc.Add("boss@here.com");
mailer.Message.Subject = "Meeting request";
mailer.Message.BodyHtmlText = "<html><body>Can we meet today?</body></html>";

mailer.Message.Attachments.Add(@"C:\Temp\details.doc");
mailer.Send();

Dim mailer As Smtp = New Smtp()
mailer.SmtpServers.Add("mail.here.com")
 
' Set From address as a single string.
mailer.Message.From.AsString = "John Doe <john.doe@here.com>"
 
' Add 1st Reply-To address.
mailer.Message.ReplyTo.AddFromString("John Doe <jdoe@here.com>")
 
' Add 2nd Reply-To address (no display name).
mailer.Message.ReplyTo.Add("noname@here.com")
 
' Specify "To" as a single string containing 2 e-mail addresses.
mailer.Message.To.AsString = "Jane Doe <jane.doe@there.com>, Alice <alice@there.com>"
 
' Add 3rd and 4th "To" addresses.
mailer.Message.To.AddFromString("mike@nodisplayname.com, Liz <liz@somewhere.com>")
 
' Specify 2 "CC" addresses separately, with different syntax.
mailer.Message.Cc.AddFromString("Bob Smith <bob@example.com>")
mailer.Message.Cc.Add("john.doe@here.com", "John Doe")
 
' Specify BCC (no need to supply display name as BCC header will be removed anyway).
mailer.Message.Bcc.Add("boss@here.com")
 
mailer.Message.Subject = "Meeting request"
mailer.Message.BodyHtmlText = "<html><body>Can we meet today?</body></html>"
mailer.Message.Attachments.Add("C:\Temp\details.doc")

In other words, it's possible to specify e-mail addresses in many ways so that you can always choose the most convenient method for you (and even combine different methods).

To learn more on setting e-mail headers, refer to Set From, Reply-To, Return-Path, To, CC, BCC, Priority and other headers in e-mail guide.

Send if server requires SMTP authentication

Most SMTP servers require clients to authenticate themselves in order to relay e-mails to external domains. In most cases, you just need to set your SMTP username and password in addition to the SMTP relay host name:

Smtp mailer = new Smtp();
mailer.SmtpServers.Add("mail.domain.com", "username", "password");

Dim mailer As Smtp = New Smtp()
mailer.SmtpServers.Add("mail.domain.com", "username", "password")

The above enables MailBee.NET to perform ESMTP authentication before sending the e-mail. Note that some servers might require you to use your full e-mail address (username@domain.com or even domain.com\username), not just username.

If your SMTP server requires another sort of authentication (like POP-before-SMTP) or you would like to learn more, refer to SMTP authentication in detail guide.

Send if server requires SSL

Most SMTP relay servers nowadays require clients to establish secure SSL connection with the server. MailBee.NET can automatically enable SSL mode for some popular e-mail services (like Gmail) but in general case you should specify SSL settings manually.

Usually, SMTP-over-SSL port is 465 (while the regular SMTP port is 25). If you specify port 465 for SMTP server, MailBee.NET will automatically enable SSL mode for it:

Smtp mailer = new Smtp();
mailer.SmtpServers.Add("mail.domain.com", "username", "password").Port = 465;

Dim mailer As Smtp = New Smtp()
mailer.SmtpServers.Add("mail.domain.com", "username", "password").Port = 465

By default, MailBee.NET uses the most secure SSL protocol supported by the server (usually, TLS).

You can also explicitly specify SSL mode for any port and set other parameters. To learn more on SMTP-over-SSL configuration, refer to SMTP over SSL (Gmail.com, Live.com, certificates) guide.

Send to e-mail address with international domain (IDN)

You can use EmailAddress.ToIdnAddress, EmailAddressCollection.ToIdnAddress or EmailAddress.EscapeIdnDomain methods to convert domain part of a e-mail address, a collection of addresses or any e-mail string into Punycode format. This translates international domain names to ASCII. You can safely IDN-ize normal Latin e-mail addresses as well, they will be left intact.

// Add IDN-ized email to To list.
mailer.To.Add(new EmailAddress("user@international.domain").ToIdnAddress());

// IDN-ize already existing To list.
mailer.To.AsString = "user@international.domain";
mailer.To = mailer.To.ToIdnAddress();

// IDN-ize From.
mailer.From = new EmailAddress("user@international.domain").ToIdnAddress();

// IDN-ize any string.
mailer.Message.Headers["Some custom header"] = EmailAddress.EscapeIdnDomain("user@international.domain");

' Add IDN-ized email to To list.
mailer.To.Add(New EmailAddress("user@international.domain").ToIdnAddress())

' IDN-ize already existing To list.
mailer.To.AsString = "user@international.domain"
mailer.To = mailer.To.ToIdnAddress()

' IDN-ize From.
mailer.From = New EmailAddress("user@international.domain").ToIdnAddress()

' IDN-ize any string.
mailer.Message.Headers("Some custom header") = EmailAddress.EscapeIdnDomain("user@international.domain")

Account part of e-mail address is not touched. IDN is about domains, not account names. To send to international local names, domain IDN-ize is not enough, you also need to encode e-mail addresses' local parts into UTF-8. To achieve that, you can just tell MailBee to encode all requests it sends to the server in UTF-8 rather than in system's default encoding:

mailer.RequestEncoding = System.Text.Encoding.UTF8;
mailer.Send();

mailer.RequestEncoding = System.Text.Encoding.UTF8
mailer.Send()

Send e-mail directly without SMTP relay server

To send without any SMTP relay server with a single of code and without creating an instance of Smtp class, you can use Smtp.QuickSend method. See Send e-mail in a single line of code topic for examples.

The below is a typical example of sending an e-mail without SMTP relay:

Smtp mailer = new Smtp();
mailer.DnsServers.Autodetect();
mailer.From.Email = "joe@domain.com";
mailer.To.Add("mike@company.com");
mailer.Subject = "Test message";
mailer.BodyPlainText = "Just a test";
mailer.Send();

Dim mailer As Smtp = New Smtp()
mailer.DnsServers.Autodetect()
mailer.From.Email = "joe@domain.com"
mailer.To.Add("mike@company.com")
mailer.Subject = "Test message"
mailer.BodyPlainText = "Just a test"
mailer.Send()

Note that direct send has a number of limitations in comparison with normal send through SMTP relay server. To learn more, refer to Direct send without SMTP relay server guide.

Verify e-mail address without sending actual e-mail

To check if an e-mail address is valid, you can use Smtp.ValidateEmailAddressSyntax and Smtp.TestSend methods:

To check bulk of addresses, consider using EmailAddressValidator component.

Smtp mailer = new Smtp();

// Get ready for DNS MX lookup.
mailer.DnsServers.Autodetect();

// Set sender and recipient.
mailer.From.Email = "j.doe@domain.com";
mailer.To.Add("lisa@company.com");

// Validate the e-mail address syntax.
Console.WriteLine(
    Smtp.ValidateEmailAddressSyntax("lisa@company.com").ToString());

// Verify the e-mail address.
Console.WriteLine(
    mailer.TestSend(SendFailureThreshold.AnyRecipientsFailed).ToString());

Dim mailer As New Smtp()

' Get ready for DNS MX lookup.
mailer.DnsServers.Autodetect()

' Set sender and recipient.
mailer.From.Email = "j.doe@domain.com"
mailer.To.Add("lisa@company.com")

// Validate the e-mail address syntax.
Console.WriteLine( _
    Smtp.ValidateEmailAddressSyntax("lisa@company.com").ToString())

' Verify the e-mail address.
Console.WriteLine( _
    mailer.TestSend(SendFailureThreshold.AnyRecipientsFailed).ToString())

Refer to Validate e-mail address via syntax check and DNS MX lookup topic for the more advanced sample, and other notes.

Exceptions and errors

The sample below sends an e-mail message and saves it into a file upon sending. All "expected" exceptions are caught. "Expected" are those like SMTP and file I/O errors. However, we don't catch license key errors (although you can do this if you need to). The exception handling is structured, we use different handlers for different exceptions and fall back to the general MailBeeException if nothing more special found:

Smtp mailer = new Smtp();

mailer.SmtpServers.Add("smtp.here.com", "joe@here.com", "secret");

mailer.Message.From.AsString = "Joe D. <joe@here.com>";
mailer.Message.To.AsString = "Carl S. <carl@there.com>";
mailer.Message.Subject = "Greetings from Joe";
mailer.Message.BodyPlainText = "Hi there!";

bool sent = false;

try
{
    mailer.Send();
    sent = true;
    Console.WriteLine("Sent successfully");
}
catch (MailBeeSmtpNegativeResponseException e)
{
    Console.WriteLine("Exception message: " + e.Message);
    Console.WriteLine();
    Console.WriteLine("MailBee.NET error code: " + e.ErrorCode.ToString());
    Console.WriteLine();
    Console.WriteLine("SMTP response code: " + e.ResponseCode.ToString());
    Console.WriteLine();
    Console.WriteLine("SMTP reply: " + e.ResponseString);
    Console.WriteLine();
    Console.WriteLine("Server IP: " + e.RemoteEndPoint.Address.ToString());
}
catch (MailBeeException e)
{
    Console.WriteLine("Exception: " + e.ToString());
    Console.WriteLine();
    Console.WriteLine("Exception message: " + e.Message);
}

if (sent)
{
    try
    {
        mailer.Message.SaveMessage("C:\Temp\message.eml");

        Console.WriteLine("Sent successfully");
    }
    catch (MailBeeIOException e)
    {
        Console.WriteLine("Exception message: " + e.Message);
        Console.WriteLine();
        Console.WriteLine("MailBee.NET error code: " + e.ErrorCode.ToString());
        Console.WriteLine();
        Console.WriteLine("InnerException: " + e.InnerException.ToString());
    }
}

Dim mailer As New Smtp()

mailer.SmtpServers.Add("smtp.here.com", "joe@here.com", "secret")

mailer.Message.From.AsString = "Joe D. <joe@here.com>"
mailer.Message.To.AsString = "Carl S. <carl@there.com>"
mailer.Message.Subject = "Greetings from Joe"
mailer.Message.BodyPlainText = "Hi there!" 

Dim sent As Boolean = False 

Try
    mailer.Send()
    sent = True
    Console.WriteLine("Sent successfully")
Catch e As MailBeeSmtpNegativeResponseException
    Console.WriteLine("Exception message: " & e.Message)
    Console.WriteLine()
    Console.WriteLine("MailBee.NET error code: " & e.ErrorCode.ToString())
    Console.WriteLine()
    Console.WriteLine("SMTP response code: " & e.ResponseCode.ToString())
    Console.WriteLine()
    Console.WriteLine(("SMTP reply: " & e.ResponseString))
    Console.WriteLine()
    Console.WriteLine("Server IP: " & e.RemoteEndPoint.Address.ToString())
Catch e As MailBeeException
    Console.WriteLine(("Exception: " & e.ToString()))
    Console.WriteLine()
    Console.WriteLine(("Exception message: " & e.Message))
End Try 

If sent Then
    Try
        mailer.Message.SaveMessage("C:\Temp\message.eml")

        Console.WriteLine("Sent successfully")
    Catch e As MailBeeIOException
        Console.WriteLine(("Exception message: " & e.Message))
        Console.WriteLine()
        Console.WriteLine("MailBee.NET error code: " & e.ErrorCode.ToString())
        Console.WriteLine()
        Console.WriteLine("InnerException: " & e.InnerException.ToString())
    End Try
End If

The special case is asynchronous methods. If the method which executes on a worker thread throws an unhandled exception, the thread silently dies and the application never knows what happened. Always catch all exceptions in worker threads and analyze them.

For more details on processing errors and exceptions in MailBee.NET, refer to Handle exceptions and errors guide.

MS Exchange SMTP issues

When your SMTP relay server is MS Exchange, keep in mind the following facts:

1. MS Exchange by default does not even run SMTP service. Make sure it's started.
2. Often, SMTP service operates on SSL ports only. If so, refer to Send if server requires SSL (like Gmail) topic on how to send over SSL.
3. Even if SMTP service operates on a regular port 25, MS Exchange might require you to use STARTTLS to enable SSL on the connection. Refer to SMTP over SSL (Gmail and others) guide for details.
4. SMTP service may require you to use secure authentication (e.g. NTLM or GSSAPI). Refer to SMTP authentication in detail guide for details.
5. MS Exchange may be configured to require you to authenticate as "domain\account" or even "domain\workstation\account" while most other servers accept "account@domain" or simply "account".
6. With MS Exchange, you may need to increase timeout value. This is because MS Exchange may send "the message was accepted" response after more than 30 seconds since it had received the message data. The default timeout in MailBee.NET is 20 seconds but it's increased to 40 seconds when waiting for response to DATA command. Still, 40 seconds may be not enough in some cases.
7. SMTP service of MS Exchange claims that it supports ESMTP CHUNKING extension (and thus MailBee.NET takes advantage of that) but in fact Exchange's CHUNKING can slow down the performance due to SMTP Tar Pitting or even not work at all. SMTP Tar Pitting is a setting of MS Exchange for limiting the throughput of the server. It you experience any issues, disable CHUNKING:

server.SmtpOptions = ExtendedSmtpOptions.NoChunking (assuming server is SmtpServer object instance).

Log file of SMTP conversation

You can enable logging of SMTP conversation between MailBee.NET client and the server in a number of ways. You can use logging into a file or memory, subscribe to Smtp.LogNewEntry event which raises each time a new log record is about to be created, and much more.

Logging is useful for trouble-shooting and tracking all the activity for later use. The code below enables logging of all the activity of Smtp object into a file and clears that file:

Smtp mailer = new Smtp();
mailer.Log.Enabled = true;
mailer.Log.Filename = @"C:\Temp\log.txt";
mailer.Log.Clear();

Dim mailer As Smtp = New Smtp()
mailer.Log.Enabled = True
mailer.Log.Filename = "C:\Temp\log.txt"
mailer.Log.Clear()

To learn more on file or memory logging, refer to Log files and memory logs in detail guide.

Troubleshoot common sending errors and non-delivery

Typical issues you may face and their possible remedy:

• The application does not run
  • The license key is not set correctly. See Import namespaces and set license key topic.
• The web application does not run
  • ASP.NET virtual directory is not configured as an application in IIS. In IIS Manager, enable Application for the given web site or virtual directory.
  • ASP.NET v2.0 or v4.0 is disabled (although it may be installed). In IIS Manager for the given web site of virtual directory, check that ASP.NET version being used is 2.0 or higher (4.0 or higher is you're using .NET 4.5 optimized version, MailBee.NET.45.dll).
  • Make sure MailBee.NET.dll actually exists in /bin folder and the application does have permission to read this file.
• Can't send e-mail at all
  • SMTP port 25 blocked, open it (may not be possible if the port is blocked by your ISP). Some SMTP servers support alternate ports like 587 or SMTP-over-SSL port 465.
  • Your relay server requires SSL connection, use dedicated SSL port 465 or use STARTTLS over regular port 25. See Send if server requires SSL (like Gmail) topic for details.
  • You're trying to send to SSL port as if it were a regular port, or vice versa. See above on how to correctly send via dedicated SSL port or via "SSL over regular port" (STARTTLS).
  • SMTP authentication required. See Send if server requires SMTP authentication topic on now to enable it.
  • SMTP authentication failed due to incorrect username or password. The server may expect username as "account@domain" while you supplied just "account", or vice versa.
  • Secure SMTP authentication failed due to errors in its implementation on the server. See Fine-tune SMTP authentication process topic to tell MailBee.NET to use insecure authentication methods.
  • MS Exchange specific issue. See MS Exchange SMTP issues topic for further suggestions.
  • Check if you can send this e-mail with another SMTP client which is installed on the same computer as MailBee.NET. Another SMTP client should use exactly the same settings like ports, SSL mode, authentication, etc. Note that MS Outlook is not an SMTP client because it usually works via MAPI rather than SMTP. Mozilla Thunderbird is a good example of an SMTP client.
• Can't send e-mail to external domains
  • SMTP authentication required. See above.
• E-mail is sent but never appears in the recipient's inbox
  • Check if you can send exactly the same e-mail with another SMTP client which is installed on the same computer as MailBee.NET, and that e-mail gets delivered.
  • Check Spam folder of the recipient. If the e-mail is there, the receiving host thinks it's spam (maybe, you got black-listed or the e-mail content looks spam-alike).
  • Set SmtpServer.HelloDomain property to the external domain name or IP address of the sending machine. E.g. mailer.SmtpServers[0].HelloDomain = "sending.host.com" in C# syntax (assuming mailer is Smtp instance and there is an SmtpServer object already in the collection). See Send custom Hello message to server topic for details.
  • In case of "direct send" mode, set DirectSendServerConfig.HelloDomain property instead. E.g. mailer.DirectSendDefaults.HelloDomain = "sending.host.com".
  • Make sure the IP address of the SMTP relay server is not black-listed.
  • Make sure the sending host has all the required DNS records including MX, PTR, SPF, and they are all properly configured.
• E-mail gets sent too slowly
  • If your server is MS Exchange, see MS Exchange SMTP issues topic on how to disable CHUNKING.
  • Gmail and many other servers insert significant delays between SMTP commands. They do this intentionally to limit the throughput, as a security and anti-spam measure (if the client sends spam, smaller throughput won't allow sending large volumes of it). See Log file of SMTP conversation topic on how to enable logging and see if the server delays its responses to the client.
• Can send single e-mail but 2nd (10th, 300th, etc) e-mail fails
  • The server may be configured to limit the maximum number of e-mails per session or from a single IP address per hour. Consider using MailBee.NET Queue. To learn more, refer to Submit to MailBee.NET Queue for increased or limited throughput topic.
• E-mail looks incorrect (international characters garbled, pictures not displayed in HTML, etc)
  • If there is a problem with international characters, set Smtp.Charset property. Read more in Compose international e-mail guide.
  • If HTML e-mail is missing inline pictures, refer to Send HTML e-mail with embedded pictures and Send e-mail created from web page content topics on how to properly embed inline pictures and other linked resources.

As a general suggestion, read carefully the exception message as it may already provide some useful information, and always enable logging when you face sending errors. The log file is a very helpful source of the debug information which you can use to understand and fix the issue or send it to AfterLogic Support Team for further analysis.

To learn how to deal with logging, see Log file of SMTP conversation topic. To submit the log file to AfterLogic, create a ticket at http://helpdesk.afterlogic.com and upload the file there.

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