I just migrated an ASP.NET 4 application that sends an email attachment from a Win Server 2008 R2 to 2012. I'm using Visual Studio 2010 and when I debug the project works and I get the email with the attachment but this is through the localhost. I'm using a pod51008.outlook.com account in my smtp settings within the web.config and I can't get it send the email. Technically, I'm able to access the URL and login. Once I login I should be able to click button with the instructions to send email with attachment to my user account but instead I get my user-defined error message.

Here is the web.config file:

  <smtp from="online_account@domain.org">
    <network host="pod51008.outlook.com" port="587" userName="online_account@domain.org" password="password" enableSsl="true" />

Here is the email subroutine code:

Private Sub email(ByVal att As String)
        Dim sendfrom As MailAddress = New MailAddress("online_account@domain.org", "Email with attachment")

        Dim sendto As MailAddress = New MailAddress(EMP.Email)
        Dim attachmentFile As New Attachment(att)
        Dim mymessage As New MailMessage(sendfrom, sendto)
        With mymessage
            .Subject = "Email with attachment "
            .Body = "<br/></br/> Email message"
            .IsBodyHtml = True
        End With
        Dim smtpclient As New SmtpClient()
        smtpclient.EnableSsl = True
    Catch ex As Exception
        errormsg.Text = "Error Sending Email, please contact Help Desk"
    End Try
    errormsg.Text = "<div align='center'>An email has been sent to " & EMP.User_Email & ".</div><br/>"
End Sub

SMTP is enabled within the Win Server 2012 I don't think I need this since I'm using the outlook account to send the email (please correct me if I'm mistaken). At least that's the way I had it in Win 2008 R2 and this was working properly.

I've been looking everywhere but all I could find where SMTP configurations to test within the server. Any help will be greatly appreciated!

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