This document was written using Windows Server 2008 R2 running IIS version 7.5 and ASP.NET scripting technology for sending email. If you require SSL/TLS, you will need to configure those elements separately.
Before you get going, you'll need to set up IIS in order to support SendGrid integration. This tutorial assumes that you have set up a working site and that the root directory tests as valid.
If you want to configure additional security to the localhost IIS 6.0 server you would set it here and match the same authentication in the IIS 6.0 GUI.
Once the SMTP Server service is installed, the IIS 6.0 virtual server technology is activated, and the IIS 6.0 administration snap-in will now be active.
At this point you will need to configure an SMTP domain that relays messages to SendGrid. Please follow Microsoft's instructions.
First, let's test using Telnet. Open up a telnet client within Windows. You do that in the Command Prompt by entering the following:
telnet localhost 25
Now, with telnet running, enter the following commands just as you see them, pressing ENTER for each new line (if configured correctly, the server won't do anything until you enter the period):
EHLO yourdomain.com MAIL FROM: email@example.com RCPT TO: firstname.lastname@example.org DATA This is a test email for SendGrid operations. .
EHLO command with your domain inserted tells the mail server which domain it will be sending from. The
MAIL FROM: command is a standard MIME entry for that inserts the email address of the sender. The
RCPT TO: command tells the server to which address to send the message. The
DATA command tells the server that the next incoming information is the body of the message. Finally, after the data is entered, the period (.) tells the server you are done. When you press Enter, it will send the message. It's quite nice to have servers to handle all this mess, isn't it!
If these manually entered commands work, then you should have the following success code returned:
250….Queued mail for delivery
You can also test using the logging feature we had you activate earlier. You can view the logs by navigating to and opening the IIS 6.0 7.5 log files with a text editor. It will probably be under the C:\Windows\System32\LogFiles directory unless you changed the log file location during installation.
Notice, highlighted in blue below, that the server sent an email and that it went through various OutboundConnectionCommand and Outbound ConnectionResponse steps. These along with the information of the various stages of EHLO, AUTH, MAIL, RCPT, DATA and quit that the email was sent successfully.
Finally, you can confirm that your configuration is working by logging into our site. Login into our web UI using your SendGrid credentials. On the main Dashboard tab you will see a list of messages that were recently sent through our service. This number should increment by one each time you either use telnet to send an email or you use a ASP.NET test script.