Setup and Configure SMTP Server on Windows Server 2012

The steps to setup and configure an SMTP Server or mail relay on Windows Server 2012 are very similar to those for Windows Server 2008 except for a few differences. Confusion has arisen due to GUI changes in Server 2012, which has led me to create this post to help anyone that requires explicit step-by-step instructions.

Note: The exact steps for installing SMTP Server on Windows Server 2008 can be found in this previous post of mine.

Installing the SMTP feature

1. Click on the Server Manager icon in the bottom left-hand corner to load the Server Manager Dashboard:

20141101005404

Alternatively, click on the Powershell icon to its right and enter servermanager.exe at the prompt to load the Server Manager Dashboard:

PS C:\Users\Admin> servermanager.exe

2. When the Server Manager Dashboard loads, click on Add roles and features in the center pane as highlighted below:

20141101010748

The Add Roles and Features Wizard will load, click Next to go past the initial Before You Begin Page:

20140924014048

3. In the Installation Type section, select Role-based or feature-based installation and click Next:

20140924014128

4. In the Server Selection section, select your server, in my example below, my server is called 2012, then click Next to proceed:

20140924014215

5. In the Server Roles section select Web Server (IIS) as highlighted below and click Next:

20140924014306

Doing so will initiate a prompt to install the required IIS Management Console. Ensure you check the Include management tools (if applicable) box per the below and click Add Features to proceed:

20140924014441

6. In the Features section, select the SMTP Server feature then click Install to proceed:

20140924014555

You will prompted to install services and features required by the SMTP Server. Ensure you check the Include management tools (if applicable) box per the below and click Add Features to proceed:

20140924014632

7. You will now be presented with the Web Server Role (IIS) section. Click Next to proceed:

20140924014741

In the Role Services section, scroll down and under Management Tools select the services to match those checked in screenshot below then click Next to proceed:

20140924015141

8. The Confirmation section will show all the role and feature configuration options you previously selected:

20140924015230

Click Install to start the installation:

20140924015320

The installation should complete shortly. You nay need to reboot your server to fully complete the installation.

Configuring the SMTP Server

The next step is to configure SMTP. To do so we will need to open Internet Information Services (IIS) Manager 6. 10. Click on the Server Manager icon per step 1 to load the Server Manager Dashboard. Then click Tools and then click on Internet Information Services (IIS) 6.0 Manager to load IIS Manager 6:

20140924022404

9. In IIS 6 Manager, expand the server name, in my example below it is 2012, then right-click on SMTP Server and select Properties:

20140924022612

10. In the General tab, unless you want the SMTP Server to use a specific IP address,  leave the settings as they are so that the IP address is set to (All Unassigned):

20140924023027

11. To proceed, click on the Access tab:

20140924023125

12. Click on the Authentication button and ensure Anonymous access is checked and then click OK:

20140924023219

13. Once back in the Access tab, click on the Connection button. Select Only the list below and then click Add. Enter 127.0.0.1 as the IP address and then click OK:

20140924023339

The Connection setting controls which computers can connect to the SMTP server and send mail. By granting only localhost (127.0.0.1) access, limits only the server itself the ability to connect to the SMTP server. This is a requirement for security. Click OK to return to the Access tab and then click on the Relay button. Enter 127.0.0.1 as the IP address and then click OK:

20140924023442

The Relay section determines which computers can relay mail through this SMTP server. By only allowing the localhost IP address (127.0.0.1) relay permissions it means that only the server itself can relay mail. Conversely, it prevents the SMTP server from being an open relay and being used to send unsolicited spam email by other computers on the internet, which could lead to the SMTP server being blacklisted.

14. Next, go to the Messages tab. Here you can enter an email address where copies of non-delivery reports are sent to. You can also configure the location of the Badmail director, however, the default setting should suffice:

20140924023556

15. Next, go to the Delivery tab:

20140924023648

16. Click on the Outbound Security button and ensure Anonymous access is selected. As the only server that can connect and relay mail through the SMTP server is localhost this security settings is fine:

20140924023728

17. Click OK to return to the Delivery tab and then click on Outbound Connections. Leave the defaults as they are:

20140924023810

18. Click OK to return to the Delivery tab and then click on Outbound Connections, then click on the Advanced button:

20140924023903

Here you will need to enter the fully-qualified domain name of the SMTP server. This will be the host name or A record that has been created in your DNS zone file. This is straight-forward to do but you will have to confirm how you do this with the party that manages DNS for your domain. I have entered mail.vsysad.com as this is fully-qualified. If you click on the Check DNS button you can confirm whether your chosen name resolves successfully. In my case it does as I see the following:

20140924023952

19. Click OK and then OK again to exit the SMTP Virtual Server Properties. You can also perform this test by running nslookup to confirm the existence of the host name as well as confirming the IP address it resolves to – which should the IP address of your server:

20141105035933

You can also load the nslookup command from PowerShell also:

20141105040434

Please note that DNS is crucial to successful email delivery. If your SMTP server cannot resolve the domains it is trying to send messages to then it will fail. Ensure that the DNS servers you have configured are able to resolve DNS queries successfully. From the above screenshot you can see that the DNS server I have configured, cachens2.dfw1.rackspace.com, was able to successfully resolve my SMTP server’s hostname, mail.vsysad.com. This is one of Rackspace’s many DNS servers and I am 100% confident it works fine.

The reason I am highlighting this is because if your SMTP Server sits within a corporate network it will likely use an internal DNS server. Often these are only configured to resolve internal namespaces therefore resolving external hostnames may fail. Also, firewall rules may block your SMTP Server from querying any DNS servers so please check and ensure DNS queries are resolved successfully and if not make sure it get fixed before going onto the testing phase below.

Another very important point about DNS is that you must ensure that you have a PTR record for reverse DNS lookups configured. The PTR record allows your SMTP Server’s public IP address to be resolved back to your hostname. Some of the major email providers perform revers DNS lookups of  mail servers connecting to them as a security measure to check their credibility or reputation. Your web host should have a control panel that allows you to configure reverse DNS if you have a dedicated public IP address. Not having a PTR record will not guarantee email delivery failure but it will very likely delay email delivery and at worst may result in your messages being blocked and your host being blacklisted. I highly recommend you you configure a PTR record for your server.

Follow the instructions in this post which shows you how to verify correct DNS configuration using the SMTPDIAG tool.

20. The last configuration step will be to set the SMTP Service to Automatic so that it automatically starts when the server boots up. Open up the Powershell console and run the command below to enable this setting:

PS C:\Users\Admin> set-service smtpsvc -StartupType Automatic

Then run the command below to confirm that the service is actually running:

PS C:\Users\Admin> get-service smtpsvc

Status   Name               DisplayName
------   ----               -----------
Running  smtpsvc            Simple Mail Transfer Protocol (SMTP)

If the SMTP Service is not running the command will return a status of Stopped. If that is the case then run the command below to start it:

PS C:\Users\Admin> start-service smtpsvc

We are now ready to test the configuration.

 Testing the SMTP Server

The next step is to verify that the SMTP server is able to send email successfully. To do this follow the steps below:

21. Create a text file on your desktop called email.txt and paste the following into it, remembering to change the email address information to reflect your own details:

From: blog@yourdomain.com
To: email@yourdomain.com
Subject: Email test

This is the test body of the email

.

22. Save the changes to email.txt and then copy the file to C:\inetpub\mailroot\Pickup. The SMTP server monitors this folder and when it detects the email.txt file, it will read the contents and send the email to the address in the To: section. This should happen almost immediately.

23. Check the email address the email was sent to and it should arrive shortly – the email was sent to my Gmail account:

20130429184511

A much easier, alternative way of doing this is to use PowerShell. To do so, launch the console and simply run the command below, ensuring that you complete the sending and receiving email addresses plus the subject and body text:

PS C:\Users\admin> Send-MailMessage -SMTPServer localhost -To xxxxx@gmail.com -From blog@vsysad.com -Subject "This is a test email" -Body "Hi Japinator, this is a test email sent via PowerShell"

The above command sent an email to my Gmail account, a screenshot of the email generated is below:

20131031223718

You can save the above command in a file with a .ps1 (PowerShell) file extension and run it whenever you need to test sending/routing of mail.

Apparently there’s more than one way to skin a cat. There’s also another way to test your mail relay server. You can use an email web form application which is similar to a contact us page on a website which allows you to post some feedback, which then uses an SMTP Server to deliver the messages to specific email contacts such as info@yourdomain.com that monitor this information. See this post to learn how to do this using an ASP.NET 4.0 C# email web form application.

That’s all there is to it! Now you have a fully functioning STMP server that can successfully send emails. Many of the companies that I have worked with use this method to send emails generated by their web applications.

If emails are not being successfully delivered you may notice that messages are building up in specific SMTP folders. Visit this post to understand the purpose of each SMTP folder and how to approach issues when messages are queuing up in those folders.

References:
How to test outbound mail flow with a file in the Pickup folder
IIS SMTP Folder Structure and how SMTP service works

Create a WordPress blog on Windows Server 2008 R2, IIS 7.5 and MySQL

20130502200705I think it is fitting that my first ever post on this WordPress Blog would be about setting up a WIMP server (Windows Server 2008 R2, IIS, MySQL & PHP).

Being a former Windows Systems Administrator I wanted to keep as many components running on familiar Microsoft applications (IIS 7.5 & SQL Server 2008 R2) and found this article explaining how to do it. However, at the time of writing this article I found that the WordPress on SQL Server (wp-sqlsrv) distribution was unavailable* so the only option was to use MySQL. In retrospect I am very happy with this outcome as the process of learning about MySQL has been very enjoyable and so far has proven to be a very stable and easy-to-use database application .

* Please note that the WordPress on SQL Server (wp-sqlsrv) distribution is now available.

The Environment

  • Server: Rackspace Cloud VM running Windows Server 2008 R2
  • Web server: IIS 7.5
  • Database application: MySQL

This blog you are reading is running off the environment above. So far I have found it to be an excellent blogging platform.

Install IIS 7.5

Logically, the first step is to install the web server application, IIS 7.5. From this point onwards I will simply refer to it as IIS.  To do so, perform the folowing steps:

1. Click Start > Run then enter servermanager.msc in the Open dialogue box then click OK  to load Server Manager:

C:\>servermanager.msc

2. Once Server Manager has loaded, right-click on Roles and click Add Roles, which initiates the Add Roles Wizard:

3. Click Next in the Before You Begin section:

4. Select Web Server (IIS) on the Select Server Role section and click Next:

20120416220536

5. Select the IIS services to be installed on the Select Role Services page. Keep the defaults but also select the CGI check box under Application Development. This enables both the CGI and FastCGI services which is required to use PHP:

6. Click Next and on the Confirmation page click Install.

7. Once the installation has completed, click Start > Run and then enter inetmgr in the dialogue box then click OK to load Internet Information Services (IIS) Manager. This will fire up IIS Manager and you will see IIS running and configured according to the options you selected earlier:

For more information, this article shows how to install IIS 7.5 with default settings and this article shows how add the CGI feature as described above.

Configure IIS 7.5

We now need to configure IIS in preparation for WordPress:

8. Click Start > Run and enter CMD in the dialogue box and then click OK.

9. At the command prompt enter the following and then hit enter on the keyboard:

md C:\Websites\Wordpress

This creates the directory where the new WordPress site will be located.

10. Open IIS Manager and click on Sites.

11. Right-click on Sites and then click Add Web Site:

In the Add Web Site dialogue box enter these details:

  • Name: WordPress
  • Physical path: C:\Websites\Wordpress
  • Bindings: All Unassigned. If your server has multiple IP addresses and you want the site to listen on a specific IP address select it from the drop-down box.
  • Host name: www.yourdomain.name. This should contain the fully-qualified domain name for your blog site.

Once all the sections have been completed click OK. You will now see the WordPress site under the Sites folder.

12. Click on Application Pools and in the middle pane you will see an application pool named WordPress. Right-click on it and select Advanced Settings:

13. Find the setting Enable 32-Bit Applications and click the drop-down box and click True. Click OK to save the settings:

20120417065550

We will leverage the improved security in IIS 7.5 by utilising ApplicationPoolIdentity. More information about this can be found here.

14. Select the WordPress site in the Connections pane and then double-click Authentication:

15. Select Anonymous Authentication and in the Actions pane on the right side click Edit:

16. Then select Application Pool Identity and click OK:

17. Click Start > Run and then enter CMD in the Open dialogue box then click OK  to load a command prompt enter the following and hit enter:

icacls "C:\Websites\Wordpress" /grant "IIS APPPOOL\Wordpress":(OI)(CI)(RX,W)

This configures the WordPress application pool to have write permissions to the directory where the new WordPress site is located.

IIS is now configured and ready for PHP to be installed!

Install PHP 5.3.10 for Windows

WordPress uses PHP therefore it is the next component to be installed. We require a ‘Non Thread Safe’ version and facilitate the installation we will use the latest version that comes with an ‘Installer’. At the time of writing, version 5.3.10, has an Installer. To proceed, perform the following:

18. Go to http://windows.php.net/download/.  Find version 5.3.10, under VC9 x86 Non Thread Safe, click the Installer version to download it. Click here for a direct download.

19. Once downloaded, run the .msi setup file, click Next at the first screen and accept the EULA (End User License Agreement)  and then click Next again.

20. Keep the default installation directory, which is C:\Program Files (x86)\PHP:

21. At the Web Server Setup step select IIS FastCGI:

22. Install the following features also; Script Executable, Register *.php files to open automatically and PEAR Install:

23. Click Next then Install and then click on Finish to complete the setup:

Install PHP Manager 1.2

PHP Manager is a plugin for IIS that allows you to manage and configure PHP settings and installations.

24. Go to http://phpmanager.codeplex.com/ and click on ‘View all downloads’ and download and install the x64 version.

25. Open IIS Manager and in the Connections pane select the server name. In the middle pane you will see all installed features within IIS. Select and open PHP Manager:

26. Under the PHP Setup section select View Recommendations:

27. Select all of the recommendations and hit the OK button:

Install MySQL

At the time of writing, MySQL 5.5.21, is the most recent version available.

28. Go to http://dev.mysql.com/downloads/mysql/ and download the 64-bit MSI Installer and run the setup (mysql-5.5.21-winx64.msi)

29. Accept the EULA and click Next.

30. In the Choose Setup Type section select Typical and click Next:

31. In the Ready To Install MySQL 5.5 section click Install:

32. When the installation completes ensure Launch the MySQL Instance Configuration Wizard is ticked and then click Finish:

33. Select Standard Configuration as the configuration type and then Next:

34. Select Server Machine as the server type and then click Next:

35. In the Windows Options section ensure the settings match the image below:

36. In the security options section check Modify Security Settings, enter the root password of your choice and then click Next:

37. In the configuration section shown below click Execute:

38. Once the process completes click Finish:

Configure MySQL for WordPress

We will now create the database for WordPress within MySQL. We will do this via the command line client.

39. Click Start > All Programs > MySQL > MySQL Server 5.5 > MySQL 5.5 Command Line Client to open a MySQL command prompt:

40. Enter the root password you chose earlier in the MySQL setup and hit enter:

41. To create the WordPressDB database type the following and hit enter:

CREATE DATABASE WordPressDB;

You will receive a confirmation that the command was successful:

Query OK, 1 row affected (0.00 sec)

41. To create the wp_user and grant it access and requisite permissions to the WordPressDB database type the following and hit enter:

GRANT ALL PRIVILEGES ON WordPressDB.* TO "wp_user"@"localhost" IDENTIFIED BY "password";

Please note that the “;” signals the end of the command. To go to a second line just hit Enter without a “;” at the end of a line.

42. Type Exit and hit enter to exit the MySQL command line client.

The confirugration of MySQL is now complete. We should now have the following information available for the WordPress install:

  • Database Name: WordPressDB
  • Database User: wp_user
  • DB User Password: password

Install WordPress

Go to http://wordpress.org/download/ and download the latest version of WordPress (currently 3.3.1) and then folllow these steps:

43. Extract the WordPress files to the location of the WordPress site we created earlier in IIS – C:\Websites\Wordpress.

44. Navigate to C:\Websites\Wordpress and find the file named wp-config-sample.php and open it with Notepad, as per below:

45. Ammend the following fields in wp-config-sample.php with the MySQL database info we created earlier :

  • DB_NAME: WordPressDB
  • DB_USER: wp_user
  • DB_PASSWORD: password

The screen shot below shows the variables that need to be changed. This is telling WordPress which database (WordPressDB) to store the configuration data in MySQL and also the connection information (wp_user and password) to be used:

46. Save the file as wp-config.php

47. Type in the following into your browser to start the WordPress installation script:

http://www.yourdomain.com/wp-admin/install.php

Be sure to replace www.yourdomain.com with your domain.

48. You will now see the WordPress welcome screen:

You need to configure the following fields with your own personal information:

  • Site Title: My First WordPress Blog
  • Username: choose your username (default is admin)
  • Password: choose your password
  • Your E-mail: email@yourdomain.com

49. Click the Install WordPress button and the setup script will run and you should see the following page soon after:

20120417114254

50. Click Login to go to the Admin Login page then enter your WordPress username and password you created earlier and start blogging!