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Installation and Configuration of the
Microsoft SMTP E-mail Server

Last Modified 12/26/2006 - Article ID#: KC00003

Resort Data Processing (RDP) has fully integrated e-mail into our Windows property management system, RDPWin and the Internet Reservation Module (IRM).  This article covers setting up a Microsoft SMTP e-mail server that can be used by both the IRM and all RDPWin workstations. 

Installation and Configuration Topics

E-Mail is one of the most powerful and least expensive marketing tools available and has been fully incorporated into the core RDP system at no additional charge.  E-Mail can be sent as follows:

E-Mail Source Explanation 
RDPWin Workstation Any RDPWin workstation can send e-mail confirmations or mass e-mails. 
RDPWin Automatic E-Mail
Monitor Service
RDPWin can automatically send an e-mail confirmation to any reservation made via the IRM.Net, RDPWin or loaded by the GDS interface.  Please go here for information on configuring the RDPWin Monitor.
Crystal Reports Designer It is also possible to e-mail any Crystal report or confirmation directly from the Crystal Reports Designer.  See Using Crystal Reports Designer to E-Mail Reports without RDPWin.

All e-mail sources above require the use of Microsoft's SMTP e-mail server or username and password to authenticate with an ISP email service or an Microsoft exchange server.  See below.

Requirements for SMTP Server

The following steps are required for the SMTP Server:

Step Explanation
Windows 2003 Server A Windows 2003 server or Windows 2008 server with IIS 6.0 is required to run the SMTP server.  See Must use a Microsoft SMTP E-Mail Server.
Registered Domain Name You must have a registered domain name to pass many spam tests.   For RDP's IRM/SMTP test server this is Resortdata.com.
Static External  IP Address Purchase an external static IP address from your Internet Service Provider (ISP).  For RDP's IRM/SMTP test server this is 65.38.150.7.  Tell your ISP that your intent is to use this IP to host a website (the IRM) and that e-mails are to be sent from this website.   
FQDN
Fully Qualified Domain Name
Every external internet address must have a fully qualified domain name (FQDN).  For RDP's IRM/SMTP test server this is IRM.Resortdata.com.
Forward Lookup

DNS "A" Record 

The forward DNS lookup associates the Fully Qualified Domain Name to the external IP Address.  This is usually done by the person from whom the Registered Domain Name was purchased.  For RDP's IRM/SMTP test server the FQDN of IRM.Resortdata.com has a forward DNS lookup to 65.38.150.7.
Reverse Lookup

DNS PTR Record

Required so E-Mail 
is not treated as spam

There is a constant battle underway to stop unwanted mass e-mail (spam) and e-mail that contains viruses.  If your e-mail is treated as spam, it may be caught in a spam filter and never get to the recipient.  It is therefore important to set up your SMTP server so that e-mail sent has the greatest possibility of not being treated as spam.

Spam filters have become much more aggressive in recent years and more e-mail is treated as spam than ever before.  One potential spam test is to verify that the sending SMTP server has a valid  reverse pointer record. .  

The reverse DNS lookup associates the external IP address  to the Fully Qualified Domain Name.  Setting up the PTR record must be done by the Internet Service Provider (ISP) from who you purchased the external IP Address.  For RDP's IRM/SMTP test server the address 65.38.150.7 has a DNS PTR record to the FQDN of IRM.Resortdata.com.   Warning:  When e-mail is sent from the SMTP server it may be treated by spam if there is not a Reverse lookup record.   See "Testing Reverse Lookup" below.

SSL Certificate

Optional

A Security Certificate (SSL) is not required to send e-mail.  However, many customers purchase one for their IRM.  The common name of the SSL must be the Fully Qualified Domain Name.   For RDP's IRM/SMTP test server this is IRM.Resortdata.com.  See "Ordering and Installing a Security Certificate".  
Firewall Changes Changes will be required on your firewall to send e-mail and for the IRM, including:
  • Allow outgoing e-mail from the SMTP server (open port 25)
  • Prevent incoming e-mail from being forwarded through the SMTP server (close port 25 for incoming e-mail).   The SMTP server only sends e-mail, it never receives e-mail. 

See "Firewall Changes".

Setup SMTP Server You must set up the SMTP server on the Windows 2000/2003 server with the steps in the remainder of this document.

Must use a Microsoft SMTP E-mail Server

Whenever e-mail is sent from RDPWin or the IRM.Net it must first go to an SMTP e-mail server.  Customers must use a Microsoft SMTP server, configured as described in this document or be able to authenticate to an exchange server or ISP based SMTP server with an username and password from RDPWin.

SMTP Server Type Explanation and RDP support
ISP based SMTP Server

Not Allowed

Almost all Internet Service Providers (ISP) provide an IP address or name for their SMTP server to use with your normal e-mail client.  However, most of these ISP's will not allow a third party program like RDP's IRM or RDPWin to send e-mail using their SMTP server because of concerns about spam and viruses.  For these reasons you cannot use any ISP based SMTP server and must use the Microsoft SMTP server on either the IRM bridge server or RDP data server as defined below.
Microsoft Exchange or
other E-mail Server 
Not Allowed
Many customers already have an e-mail server, such as Microsoft Exchange, set up for use for outgoing e-mail.  Since there are over 100 different e-mail servers, all with different configurations, it is not possible for RDP to support Exchange or any other e-mail server.   You must use the Microsoft SMTP server on either the IRM bridge server or RDP data server as defined below.
Microsoft SMTP Server 

Allowed

Microsoft provides a SMTP server with every copy of Windows 2000 and 2003 server.  This is the only SMTP server supported by RDP for sending e-mail from the Internet Reservation Module (IRM) or any RDPWin workstation.  Normally the SMTP server is already installed on the IRM server.  If you do not have the IRM, the data server can be used as the SMTP server.  See "RDP Hardware Requirements"

Test with www.dnsstuff.com

After setting up your registered domain name, alias record, and reverse pointer record, please test as follows:

  1. Go to www.dnsstuff.com
  2. In the "IP Tests" area, select the "Reverse DNS Lookup" test and enter your external IP address.  This should return the machinename.registereddomainname.  In the RDP example, this is:

    65.38.150.7 PTR record: irmip07.resortdata.com. [TTL 7200s] [A=65.38.150.7]  

Test your site against a spam database lookup and a full DNS report using  www.dnsstuff.com.

Verify if SMTP Server is Already Installed

RDP suggests using the Microsoft SMTP e-mail server installed on the IRM server.  If you do not have the IRM, then install and use the Microsoft SMTP e-mail server on the data server.  To verify if the SMTP service is already installed, proceed as follows:

  1. Login to the Internet Reservation Module (IRM) server as administrator.  If you do not yet have the IRM, login to the data server as administrator.
  2. Select Start | Programs | Administrator Tools | Internet Information Services.
  3. If Internet Information Services (IIS) is installed it should start and appear similar to the diagram below, which indicates a default SMTP Virtual Server is installed.  If these are not installed, see IRM Installation Document - Customer Steps.

Restrict SMTP Connections by IP Address

After a SMTP server is installed, it must be configured to allow access from all workstations at the property and to restrict access from outside computers so that an unauthorized individual cannot send spam through your SMTP server.  There are many security techniques possible, however RDPWin only supports restricting access to the SMTP server by IP address, as follows:

  1. From the Windows 2000/2003 server that has SMTP installed, login as the administrator.
  2. Select Start | Programs | Administrator Tools | Internet Information Services.
  3. Highlight the Default SMTP Virtual Server, right click and select properties.
  4. Select the "Access" tab and then the "Connection" button.  
  5. Highlight the option for "only the list below" and click the "Add button" . 
  6. Select the "group of computers" radio button, and enter the subnet for the property.  In the example below the subnet address is 192.168.43.0 and the Subnet mask is 255.255.255.0, which allows access for all computers from 192.168.43.1 to 192.168.43.255.
  7. Click OK

Warning:   After making changes to the SMTP configuration, it may be necessary to reboot the server, even if not prompted to do so, before testing e-mail again with RDPWin or the IRM.

Restrict SMTP Relay by IP Address

Next, restrict who is allowed to relay e-mail through the SMTP server, as follows:

  1. From the Windows 2000/2003 server that has SMTP installed, login as the administrator.
  2. Select Start | Programs | Administrator Tools | Internet Information Services.
  3. Highlight the Default SMTP Virtual Server, right click and select properties.
  4. Select the "Access" tab, and then the "Relay" button.  
  5. Highlight the option for "only the list below" and click the "Add button"  
  6. Again select a "group of computers" as explained in the previous section.
  7. Make sure that "Allow all computers which successfully authenticate to relay, regardless of the list above" is NOT checked.

Warning:   After making changes to the SMTP configuration, it may be necessary to reboot the server, even if not prompted to do so, before testing e-mail again with RDPWin or the IRM.

Change Parameters on Messages in SMTP

Change the Parameters for Messages in SMTP as follows:

  1. From the Windows 2000/2003 server that has SMTP installed, login as the administrator.
  2. Select Start | Programs | Administrator Tools | Internet Information Services.
  3. Highlight the Default SMTP Virtual Server, right click and select properties.
  4. Select the "Messages" tab, and then the "Relay" button.  
  5. Remove all check-boxes. 
  6. In the "Send Copy of Non-Delivery Reports to:"  add the e-mail address of someone at your company who should be notified each time a e-mail message cannot be delivered. 
  7. Select Apply and OK

Firewall - Open Port 25 for Sending
and Close Port 25 for Receiving

Changes will be required on your firewall to send e-mail:

  • Allow sending e-mail from the SMTP server (open port 25)
  • To stop non-authorized users (spammers) from relaying e-mail though your SMTP server, block all incoming e-mail to the SMTP server at the firewall level. The SMTP server only sends e-mail, it never receives e-mail. E-Mail is received through your normal e-mail client.

Note:  Other changes are required to the firewall for the Internet Reservation Module.  See IRM Installation.

Send a Test E-mail with the
Internet Reservation Module (IRM)

To send a test e-mail with the Internet Reservation Module (IRM), proceed as follows:

  1. Go to your IRM server and login as the administrator.
  2. Start the IRM Monitor.
  3. Click the link for "Test E-Mail" and click "Get Path" on the IRM test Page screen.  
  4. There are two e-mail tests at the bottom.  Make sure to enter an outside e-mail address such as a Hotmail account.
  5. Click the button for "Send1Line" to test the e-mail from the IRM.
  6. Start your e-mail client and verify that the e-mail has been received. If the e-mail is not received, see Testing SMTP Server with Outlook Express and SMTP Server Troubleshooting Tips.

Warning:   After making changes to the SMTP configuration it may be necessary to reboot the server, even if not prompted to do so, before testing e-mail again with RDPWin or the IRM.

Sending a Test E-mail with RDPWin

To test that the SMTP server is working, send a test e-mail from RDPWin as follows:

  1. Start RDPWin.
  2. Navigate to Reporter - Configuration - Email.  A screen similar to the following appears.  Make sure to use an external e-mail address.
  3. Set the SMTP server as the static internal IP address of the SMTP server.  In the example used at the top of this document for RDP's test IRM server, this is 192.168.43.7.
  4. Click Save.  All changes must be saved before clicking "Send Test Email". 
  5. Click the "Send Test E-mail".
  6. Start your e-mail client and verify that the e-mail has been received.  If not received, see testing SMTP Server with Outlook Express and SMTP Server Troubleshooting Tips at the end of this document.

Testing SMTP Server with Outlook Express

There are many reasons why an e-mail will not be received successfully and it is not possible for RDP to troubleshoot all possibilities.  If the e-mail is not received, use the procedure below to test using 100% Microsoft tools.  If the e-mail is still not received, you can have your hardware people call Microsoft Support, since the problem will be isolated to Microsoft products only.

  1. Install Outlook Express on the IRM Bridge Server or the workstation that cannot send e-mail.
  2. Set the SMTP server to the internal IP address of the SMTP server.  See screen below for other fields.
  3. Using Outlook Express to send a test e-mail to an external e-mail address. If this e-mail is not received call Microsoft Support. The problem is then confined to Microsoft's Outlook Express and Microsoft's e-mail server and they should be able to help. If you can get Outlook Express to send an e-mail through the SMTP server then RDP will also work.
Configuration of Test Outlook Express Account

Field Setting
Incoming E-Mail (POP3) Incoming SMTP server can be set to "test@test.com" because there will be no incoming e-mail in this test.
Outgoing E-Mail (SMTP) The SMTP server must be the IP address of the Windows 2000, 2003, or XP workstation where the SMTP server is installed.  This should always be an internal address.  Do not use external SMTP servers as most of these have security that prevents programs like RDPWin and the IRM from sending e-mail.  You must use an SMTP server behind your firewall.  
Account Name The incoming e-mail server account name is not relevant for this test, since no incoming e-mail will be received.  You can use an account name of "Test".
Password The incoming e-mail server password is not relevant for this test, since no incoming e-mail will be received.  Leave this blank.  
Logon Using Secure Password Authentication

Do not check "Logon Using Secure Password Authentication".  RDP supports securing the outgoing e-mail server by IP address only.

My Server Requires Authentication Do not check "My server requires authentication".   RDP supports securing the outgoing e-mail server by IP address only, not user name and password.  Use the links below to review these topics. 

SMTP Server Troubleshooting Tips

There are many reasons why an e-mail will not be received successfully and it is not possible for RDP to troubleshoot all possibilities. Some troubleshooting tips are below:

  • Make sure e-mail is not forwarded to a SMTP server from your ISP or some other e-mail server.  E-Mail should be sent directly from the IRM test server to the firewall. See Must Use SMTP Email Server.
  • Always test with Microsoft Outlook Express, which confines the problem to Microsoft products, which allows your hardware people to call Microsoft for help.  Generally speaking, if Outlook Express works, so will RDP's IRM and RDPWin.
  • While RDP suggests using a Windows 2000/2003 server as the SMTP server, in a peer-to-peer environment without a server, a Windows XP Professional Workstation can be used.   The Microsoft Personal Firewall on the Windows XP workstation must be configured to allow access on port 25.  See SMTP Server on Windows XP.
  • The company firewall can also stop e-mail.  In this case, the RDP test e-mail will appear to work, but the e-mail will never be received.  See Open Port 25 on the Firewall for SMTP above.
  • Even if the SMTP server has is configured correctly and the firewall is also configured correctly, e-mails may still not get through.  This can occur if the Internet Service Provider (ISP) has stopped all outgoing e-mail at their firewall to prevent spam.
  • The test e-mail may not be received by the client because the client may consider the test e-mail as spam and put the test e-mail in the Junk folder.
  • The SMTP server sends e-mail to specified folders on the server first.  Verify the e-mail has cleared the Pickup folder in c:\Inetpub\Mailroot.  See SMTP Folders Incorrect.

E-Mail Related Topics

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