(SQL Server) Send Email with Hotmail (live.com) -- smtp-mail.outlook.com

Demonstrates the SMTP settings required for sending email through Hotmail (A live.com email address). The Hotmail SMTP server is smtp-mail.outlook.com and receives connections on the SMTP port 587. It expects STARTTLS to establish an explicit TLS connection.

Note: When I first tested this code, I received the following error:

550 5.3.4 554-554 5.2.0 STOREDRV.Deliver; delivery result banner

Mozilla Thunderbird also encountered the same error. I then started a browser, visited outlook.live.com, and logged in to my account. I probably hadn't done that for a very long time. I then retried running this example, and everything worked.

Also, it seems that the SMTP server hostname can be either "smtp-mail.outlook.com" or "smtp.live.com". Both worked.

Chilkat ActiveX Downloads ActiveX for 32-bit and 64-bit Windows

// Important: See this note about string length limitations for strings returned by sp_OAMethod calls.
//
CREATE PROCEDURE ChilkatSample
AS
BEGIN
    DECLARE @hr int
    DECLARE @iTmp0 int
    DECLARE @sTmp0 nvarchar(4000)
    -- This example requires the Chilkat API to have been previously unlocked.
    -- See Global Unlock Sample for sample code.

    -- The mailman object is used for sending (SMTP) and receiving (POP3) email.
    DECLARE @mailman int
    EXEC @hr = sp_OACreate 'Chilkat_9_5_0.MailMan', @mailman OUT
    IF @hr <> 0
    BEGIN
        PRINT 'Failed to create ActiveX component'
        RETURN
    END

    -- Set the SMTP server.
    -- Apparently, both "smtp-mail.outlook.com" and "smtp.live.com" are valid.
    EXEC sp_OASetProperty @mailman, 'SmtpHost', 'smtp.live.com'
    EXEC sp_OASetProperty @mailman, 'SmtpPort', 587

    -- Set the SMTP login/password (if required)
    EXEC sp_OASetProperty @mailman, 'SmtpUsername', 'myLogin@live.com'
    EXEC sp_OASetProperty @mailman, 'SmtpPassword', 'MY-HOTMAIL-PASSWORD'

    -- Create a new email object
    DECLARE @email int
    EXEC @hr = sp_OACreate 'Chilkat_9_5_0.Email', @email OUT

    EXEC sp_OASetProperty @email, 'Subject', 'This is a test'
    EXEC sp_OASetProperty @email, 'Body', 'This is a test'
    EXEC sp_OASetProperty @email, 'From', 'My Hotmail Account <myLogin@live.com>'
    DECLARE @success int
    EXEC sp_OAMethod @email, 'AddTo', @success OUT, 'Chilkat Admin', 'admin@chilkatsoft.com'

    EXEC sp_OAMethod @mailman, 'OpenSmtpConnection', @success OUT
    IF @success <> 1
      BEGIN
        EXEC sp_OAGetProperty @mailman, 'LastErrorText', @sTmp0 OUT
        PRINT @sTmp0

        EXEC sp_OAGetProperty @mailman, 'ConnectFailReason', @iTmp0 OUT
        PRINT 'ConnectFailReason = ' + @iTmp0
        EXEC @hr = sp_OADestroy @mailman
        EXEC @hr = sp_OADestroy @email
        RETURN
      END

    EXEC sp_OAMethod @mailman, 'SmtpAuthenticate', @success OUT
    IF @success <> 1
      BEGIN
        EXEC sp_OAGetProperty @mailman, 'LastErrorText', @sTmp0 OUT
        PRINT @sTmp0
        EXEC @hr = sp_OADestroy @mailman
        EXEC @hr = sp_OADestroy @email
        RETURN
      END

    EXEC sp_OAMethod @mailman, 'SendEmail', @success OUT, @email
    IF @success <> 1
      BEGIN
        EXEC sp_OAGetProperty @mailman, 'LastErrorText', @sTmp0 OUT
        PRINT @sTmp0
        EXEC @hr = sp_OADestroy @mailman
        EXEC @hr = sp_OADestroy @email
        RETURN
      END

    EXEC sp_OAMethod @mailman, 'CloseSmtpConnection', @success OUT


    PRINT 'Email Sent.'

    EXEC @hr = sp_OADestroy @mailman
    EXEC @hr = sp_OADestroy @email


END
GO