Most may not realize that there is actually a free SMTP server builtin to Windows Server all the way back to Windows 2003 and is IIS 6 technology (I know, try to suppress your nausea). The SMTP server is a feature that can be added to modern Windows Server versions via the Server Manager. Out of curiosity and due to working on a project recently utilizing the SMTP server on a Windows 2012 box, I wanted to see if the SMTP server was still an option in Windows Server 2016 TP4 and the answer is yes.
Installing the SMTP server
This is a feature found in the Add Roles and Features Wizard and is simply listed as SMTP Server.
By default, the feature wizard will add the Management tools for IIS 6 since this is an IIS 6 technology.
A reboot will not be prompted for adding this feature.
Using the SMTP Server
The SMTP Server is administered through the IIS 6 Management Console. An easy way to get there is to go to a run or command prompt and type inetmgr6.exe. You will see the IIS 6 SMTP Virtual Server manager as show below. If you right click on SMTP Virtual Server, you get a configuration box where you can configure most everything affecting mailflow.
One of the more important areas of the configuration is under Delivery and Advanced where you will see the Advanced Delivery options. Here is where you configure your mail domain.
Testing mailflow
Using powershell we can test mailflow from our SMTP server using the send-mailmessage commandlet. By default however, the server is not set to allow any open relays out of the box.
If you run the send-mailmessage commandlet from the server itself, you need to add the server’s assigned IP address to the allowed to relay list before you test. Below is the default configuration.
After you have added the appropriate IP address, you can open up a powershell prompt and use the following to test SMTP relay
Final Thoughts
The SMTP relay included in Windows Server from 2008 forward is a no frills SMTP relay that doesn’t include many options, however, if you are looking for SMTP functionality for an application or for testing, it can come in very handy. It is good to see this feature is still hanging around in Windows Server 2016.
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When you set up a multifunction device or application to send email through Office 365, there are some cases where the device or application can't connect directly to Office 365. In these cases, you need to set up Internet Information Services (IIS) to work as an intermediary.
You might want to do this in the following scenarios:
Before proceeding, review How to set up a multifunction device or application to send email using Office 365 as there may be an available option that doesn't require setting up an additional server to relay.
Note
These instructions can be modified for other SMTP relays that you might have in your organization.
What you need to know before you begin
Set up Exchange Online as an SMTP Relay Using Windows Server 2012Step 1: Install Internet Information Services (IIS)
Step 2: Install SMTP
Step 3: Set up SMTP
Step 4: Restart the IIS service and the SMTP serviceSet up Exchange Online as an SMTP Relay Using Windows Server 2008Step 1: Install Internet Information Services (IIS)
Step 2: Install SMTP
Step 3: Set up SMTP
Step 4 Restart the IIS service and the SMTP serviceHow do you know this worked?
You can test SMTP relay services without using an separate LOB application or device.
To test SMTP relay services, use the following steps.
Related Topics
Windows Server Essentials (formerly Windows Small Business Server or SBS[2]) is an integrated server suite from Microsoft designed for running network infrastructure (both intranet management and Internet access) of small and midsize businesses having no more than 25 users or 50 devices. Application server technologies are tightly integrated to provide and offer management benefits such as integrated setup, enhanced monitoring, Remote Web Workplace, a unified management console, and remote access.
Since the release of SBS 2003, the same service packs as those for Windows Server or other server products can be used to update the OS.[3][4]
Editions[edit]
Windows Server 2019 Essentials, based on Windows Server 2019, is the current version of Server Essentials, initially released in October 2018. Due to the discovery of significant issues, it was re-released with general availability on November 13, 2018.[5]
Windows Server 2016 Essentials, based on Windows Server 2016, is the previous version of Server Essentials, released in September 2016 with general availability October 12, 2016.
Windows Server 2012 R2 Essentials and Windows Server 2012 Essentials were earlier versions of corresponding releases of Windows Server.[6]
Older versions: Windows Small Business Server 2011 was available in Essentials, Standard, and Premium editions. Essentials is a scaled down version for 1 to 25 users; both the other editions are based on the Windows Server codebase and include Microsoft Exchange Servermail server, Internet Information Services (IIS) web server, Windows SharePoint Services for collaboration, Microsoft Outlook 2003 email client (not included in 2008), Routing and Remote Access Service (RRAS), Windows Server Update Services for update management across the network, and a Fax server. Up to SBS 2003, the Premium edition also included Microsoft SQL Server, Microsoft Internet Security and Acceleration Server and Microsoft Office FrontPage 2003. SBS 2008 Premium edition will not include ISA Server but will include a Windows Server 2008 license and SQL Server 2008 for running on a second server. Those upgrading to SBS 2008 Premium edition via Software Assurance will be compensated with a free license for the latest version of ISA Server.[7]
The version of Windows Server that is part of Small Business Server 2008 and Essential Business Server 2008, known as Windows Server 2008 for Windows Essential Server Solutions (WinWESS) (also known as Windows Server 2008 Standard FE)[8] is available outside the product suite, supporting a maximum of 15 Client Access Licenses.[9]
Initially, Small Business Server was marketed as an edition of Microsoft BackOffice Server. When Windows 2000 was released, it was marketed as Microsoft Small Business Server 2000, and finally was rebranded as a member of the Windows Server 2003 family. In December 2008, Microsoft also introduced a Windows Essential Business Server product aimed at medium-sized businesses, but this was discontinued in June 2010 due to low demand.
Design and licensing considerations[edit]
All editions of Windows Server Essentials since the 2011 release do not need any client access license (CAL).
Windows Small Business Server (not Essentials) had its own type of CAL, and included the user CALs for Windows Server, Exchange Server, and eventually SQL Server; the SBS CAL cost more than the Windows Server license, but less than the sum of separate access licenses for the two or three servers.
Windows Small Business Server has the following design restrictions:[10]
Unique features[edit]
Versions[edit]
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