Send Email using Hotmail/Live/Outlook/Office 365 in VB.NET

In previous section, I introduced how to send email using Yahoo account. In this section, I will introduce how to send email using Hotmail/Live/Outlook/Office 365 in VB.NET.

Introduction

Hotmail/Live/Outlook.com SMTP server address is smtp.live.com. It requires explicit SSL (TLS) connection to do user authentication, and you should use your Hotmail/Live/Outlook.com email address as the user name for ESMTP authentication. For example: your email is myid@hotmail.com, and then the user name should be myid@hotmail.com.

Server Port SSL/TLS
smtp.live.com 25, 587 TLS

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 using Hotmail/Live/Outlook.com over Explicit SSL (TLS) on 25 or 587 Port - Example]

The following example codes demonstrate how to send email using Hotmail/Live/Outlook.com in VB.NET over TLS 25 or 587 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")

            ' Your hotmail email address
            oMail.From = "liveid@hotmail.com"
            ' Set recipient email address, please change it to yours
            oMail.To = "support@emailarchitect.net"

            ' Set email subject
            oMail.Subject = "test email from hotmail account"
            ' Set email body
            oMail.TextBody = "this is a test email sent from VB.NET project with hotmail"

            ' Hotmail SMTP server address
            Dim oServer As New SmtpServer("smtp.live.com")

            ' Hotmail user authentication should use your
            ' email address as the user name.
            oServer.User = "liveid@hotmail.com"
            oServer.Password = "yourpassword"

            ' set 587 port, if you want to use 25 port, please change 587 to 25
            oServer.Port = 587

            ' detect SSL/TLS connection automatically
            oServer.ConnectType = SmtpConnectType.ConnectSSLAuto

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

            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

Hotmail SMTP OAUTH

If your account enabled two-factor authentication, you cannot login your account by normal user authentication, you should use SMTP OAUTH or App Password.

Microsoft Live SMTP servers (Hotmail, Oultook personal account) have been extended to support authorization via the industry-standard OAuth 2.0 protocol. Using OAUTH protocol, user can do authentication by Microsoft Web OAuth instead of inputting user and password directly in application.

Microsoft will disable traditional user authentication in the future, switching to Microsoft OAuth (Modern Authentication) is strongly recommended now.

Or you can generate App Passwords and use this app password instead of your user password.

Send Email using Office 365

First of all, you should go to Office 365 “Outlook” -> “Options” -> “See All Options” -> “Account” -> “My Account” -> “Settings for POP, IMAP, and SMTP access”. You will get your Office 365 SMTP server address and port. Then you can use your Office 365 SMTP server, port, user/password in the codes.

By default, Office 365 SMTP server uses 587 port and explicit SSL (TLS) connection.

Server Port SSL/TLS
smtp.office365.com 25, 587 (recommended) TLS

[VB.NET - Send Email using Office 365 over Explicit SSL (TLS) on 587 Port - Example]

The following example codes demonstrate how to send email using Office 365 in VB.NET over TLS 587 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")
            ' Your office 365 email address
            oMail.From = "myid@mydomain"
            ' Set recipient email address, please change it to yours
            oMail.To = "support@emailarchitect.net"

            ' Set email subject
            oMail.Subject = "test email from office 365 account"
            ' Set email body
            oMail.TextBody = "this is a test email sent from VB.NET project with hotmail"

            ' Your Office 365 SMTP server address,
            Dim oServer As New SmtpServer(" smtp.office365.com")

            ' user authentication should use your
            ' email address as the user name.
            oServer.User = "myid@mydomain"
            oServer.Password = "yourpassword"

            ' Set 587 port
            oServer.Port = 587

            ' detect SSL/TLS connection automatically
            oServer.ConnectType = SmtpConnectType.ConnectSSLAuto

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

            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

Office365 EWS OAUTH

If your account enabled two-factor authentication, you cannot login your account by normal user authentication, you should use SMTP/EWS OAUTH or App Password.

Microsoft Office365 EWS/SMTP servers have been extended to support authorization via the industry-standard OAuth 2.0 protocol. Using OAUTH protocol, user can do authentication by Microsoft Web OAuth instead of inputting user and password directly in application. This way is more secure, but a little bit complex.

Or you can generate App Passwords and use this app password instead of your user password.

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

Next Section

At next section I will introduce how to send email without specified SMTP server.

Appendix

Comments

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