Send Email over SSL/TLS in VB.NET

In previous section, I introduced how to send email in a simple VB project. In this section, I will introduce how to send email over SSL/TLS connection in VB.NET.

SSL and TLS Introduction

SSL connection encrypts data between the SMTP component and SMTP server to protects user, password and email content in TCP/IP level. Now this technology is commonly used and many SMTP servers are deployed with SSL such as Gmail, Yahoo and Hotmail. There are two ways to deploy SSL on SMTP server:

  • Explicit SSL (TLS)

    Using STARTTLS command to switch SSL channel on normal SMTP port (25 or 587);

  • Implicit SSL

    Deploying SSL on another port (465 or other port, you may query it from your server administrator

EASendMail SMTP component supports both ways. The connection can be specified by EASendMail.SmtpConnectType enumeration. Please see the following example code.

TLS 1.2

TLS is the successor of SSL, more and more SMTP servers require TLS 1.2 encryption now.

If your operating system is Windows XP/Vista/Windows 7/Windows 2003/2008/2008 R2/2012/2012 R2, and you got connection error with SSL/TLS connection, you need to enable TLS 1.2 protocol in your operating system like this:

Enable TLS 1.2 on Windows XP/Vista/7/10/Windows 2008/2008 R2/2012

[VB.NET - Send Email over SSL/TLS Setting - Example]

The following example codes demonstrates how to set SSL/TLS connection.

' Send email by normal TCP/IP without SSL connection
Dim oServer As New SmtpServer("localhost 25")
oServer.ConnectType = SmtpConnectType.ConnectNormal

' Send email by SSL connection with STARTTLS command switching
Dim oServer As New SmtpServer("localhost 25")
oServer.ConnectType = SmtpConnectType.ConnectSTARTTLS

' Send email by SSL connection with direct SSL.
Dim oServer As New SmtpServer("localhost 465")
oServer.ConnectType = SmtpConnectType.ConnectDirectSSL

' Send email by SSL connection with auto-detect.
' If port is 25 or 587, STARTTLS SSL will be used; otherwise direct SSL will be used.
Dim oServer As New SmtpServer("localhost 465")
oServer.ConnectType = SmtpConnectType.ConnectSSLAuto

Dim oServer As New SmtpServer("localhost 25")
oServer.ConnectType = SmtpConnectType.ConnectSSLAuto

' If server supports SSL/TLS, then SSL/TLS is used, otherwise normal TCP is used.
Dim oServer As New SmtpServer("localhost 25")
oServer.ConnectType = SmtpConnectType.ConnectTryTLS

Dim oServer As New SmtpServer("localhost 587")
oServer.ConnectType = SmtpConnectType.ConnectTryTLS

Note

Remarks: All of samples in this section are based on first section: Send email in a simple VB.NET project. To compile and run the following example codes successfully, please click here to learn how to create the test project and add reference of EASendMail to your project.

[VB.NET - Send Email over Implicit SSL on 465 port - Example]

The following example codes demonstrate how to send email over SSL connection on 465 port.

Note

To get the full sample projects, please refer to Samples section.

Imports EASendMail 'Add EASendMail namespace

Module Module1
    Sub Main()

        Try

            Dim oMail As New SmtpMail("TryIt")
            ' Set sender email address, please change it to yours
            oMail.From = "test@emailarchitect.net"
            ' Set recipient email address, please change it to yours
            oMail.To = "support@emailarchitect.net"

            ' Set email subject
            oMail.Subject = "test email from VB.NET project"
            ' Set email body
            oMail.TextBody = "this is a test email sent from VB.NET project, do not reply"

            ' Your SMTP server address
            Dim oServer As New SmtpServer("smtp.emailarchitect.net")

            ' User and password for ESMTP authentication
            oServer.User = "test@emailarchitect.net"
            oServer.Password = "testpassword"

            ' Set SSL 465 port
            oServer.Port = 465

            ' Set direct SSL connection, you can also use ConnectSSLAuto
            oServer.ConnectType = SmtpConnectType.ConnectDirectSSL

            Console.WriteLine("start to send email ...")

            Dim oSmtp As New SmtpClient()
            oSmtp.SendMail(oServer, oMail)

            Console.WriteLine("email was sent successfully!")
        Catch ep As Exception
            Console.WriteLine("failed to send email with the following error:")
            Console.WriteLine(ep.Message)
        End Try
    End Sub
End Module

[VB.NET - Send Email over TLS (Explicit SSL) on 25 or 587 port - Example]

The following example codes demonstrate how to send email over TLS (STARTTLS command, Explicit SSL) connection on 25 port.

Note

To get the full sample projects, please refer to Samples section.

Imports EASendMail 'Add EASendMail namespace

Module Module1

    Sub Main()

        Try
            Dim oMail As New SmtpMail("TryIt")

            ' Set sender email address, please change it to yours
            oMail.From = "test@emailarchitect.net"
            ' Set recipient email address, please change it to yours
            oMail.To = "support@emailarchitect.net"

            ' Set email subject
            oMail.Subject = "test email from VB.NET project"
            ' Set email body
            oMail.TextBody = "this is a test email sent from VB.NET project, do not reply"

            ' Your SMTP server address
            Dim oServer As New SmtpServer("smtp.emailarchitect.net")

            ' User and password for ESMTP authentication
            oServer.User = "test@emailarchitect.net"
            oServer.Password = "testpassword"

            ' Set 25 port, if your server uses 587 port, please change 25 to 587
            oServer.Port = 25

            ' Set TLS connection, you can also use ConnectSSLAuto
            oServer.ConnectType = SmtpConnectType.ConnectSTARTTLS

            Console.WriteLine("start to send email ...")

            Dim oSmtp As New SmtpClient()
            oSmtp.SendMail(oServer, oMail)

            Console.WriteLine("email was sent successfully!")
        Catch ep As Exception
            Console.WriteLine("failed to send email with the following error:")
            Console.WriteLine(ep.Message)
        End Try

    End Sub

End Module

SMTP Server SSL Certificate

To send email over SSL/TLS connection, you don’t need to install a certificate on your machine. The data is encrypted by server certificate public/private key pair.

SMTP Setting for Gmail, Yahoo, Hotmail and Office 365

Because most popluar email providers support or require SSL/TLS connection, so I will introduce specific setting for Gmail, Yahoo, Hotmail and Office 365 in the coming sections.

Next Section

At next section I will introduce how to send email using Gmail account in VB.NET.

Appendix

Comments

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