How to properly configure Microsoft IIS 7.5 with VMA Emailer

Windows 2008 R2 runs IIS version 7.5 and ASP.NET script that sends an email. If you use SSL/TLS, you will need separate configuration.

First what you'll need to configure is IIS in order to support VMA Emailer integration. This documentation assumes that you have configured a working site and its root directory have valid tests.

1. Start IIS 7.0/7.5 Manager in Windows.
2. Click on your working site and then the main configuration options page will be displayed on the right.
3. Double-click on the “SMTP E-mail” under the ASP.NET section.
4. In the email address field: type the email address that will be the “sender”.
5. Click on the “Deliver e-mail to SMTP server” radio button if not already enabled.
6. In the SMTP Server field: type localhost.
7. In the Port field: type 25.
8. In Authentication Settings click the “Not required” option.
9. On the right side “Actions” pane: click Apply.

How To Enable SMTP Service

1. Go to Start > All Programs > Administrative Tools > Server Manager.
2. Click on the Features item in the navigation panel.
3. Click the Add Features link to start the wizard.
4. Scroll down the list to the SMTP Server, and check the box. The Required Role Services dialog will appear, listing all of the dependencies that the SMTP server depends on to operate. Click Add Require Role Services.
5. Click Next twice.
6. Review the list of available IIS Role Services and check any that you would like to add.
7. Click Next then click Install.

The IIS 6.0 administration snap-in will be active and the IIS 6.0 virtual server technology once the SMTP Server service is installed.

How to Configure IIS 6.0 to Outbound Email Relay to VMA Emailer

1. Go to Start > All Programs > Administrative Tools > IIS 6.0 Manager.
2. Right click on the SMTP Virtual Server #1 and select the Properties option.
3. Click the box to enable logging section to assist you in configuring the server.
4. Click on Properties and check the box to activate Use Local Time For File Naming And Rollover option.
5. Click on the Advanced tab and check the following items: Date, Time, Client IP Address, User Name, Service Name, Server Name, Server IP Address, Server Port, Method, Protocol Status, Bytes Sent, Protocol Version, and Host.
6. Click OK.
7. Click on the Access tab then click the Relay button in the Relay Restrictions section.
8. Click Add, enter 127.0.0.1 and click OK. The IP will appear in the list with Access Granted.
9. Click OK Only The List Below radio button and enter 127.0.0.1 in the IP address field.
10. Click on OK to return to the Access tab as shown in the previous screenshots.
11. Select the Delivery tab and click the Outbound Security button.
12. Click on Basic Authentication where the Username will be your VMA Emailer username and the password will be your VMA Emailer password.
13. Click OK.
14. Click the Advanced button.
15. In the Smart host field: enter smtp.elasticemail.com
16. Click on OK twice and you can close the IIS 6.0 admin MMC.

How to Configure Domains

At this point, you will need to configure an SMTP domain that relays messages to VMA Emailer. Please follow Microsoft’s instructions.

Testing Your New Configuration

First, let’s test using Telnet. Open up a telnet client within Windows. You can 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: test@yourdomain.com

RCPT TO: recipient@anotherdomain.com

DATA

This is a test email for VMA Emailer operations.

The EHLO command set up with your domain shows the mail server which domain will be the from address. The MAIL FROM: command is an ideal MIME entry which inserts the sender's email address. The RCPT TO: command shows which address the message will be sent to. The DATA command tells the next information is the body of the message. Finally, after data is entered, the period (.) tells the server that you are done.

If these commands' (that were manually entered) format is correct, then you should see the success code returned:

250….Queued mail for delivery

You may also test logging feature that you activated earlier. You can see logs by navigating to the text editor and opening IIS 6.0 7.5 log files. It will be under the log file you set during installation or probably under C:\Windows\System32\LogFiles directory.

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 VMA Emailer credentials. On the main Dashboard reports 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 an ASP.NET test script.

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