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E-Mail / SMTP Server Configuration and Troubleshooting

Last Modified 04/25/2011 - MC/SW
Article ID#: KWin0167

Overview

RDP has fully integrated e-mail into RDPWin and the Internet Reservation Module (IRM or IRM.Net).  Every e-mail contains four key players:

  • Author (RDPWin) or originator of the e-mail
  • Sender (customer's internal or external SMTP server) or agent who first put the e-mail on the public internet
  • Receiver or agent who receives the e-mail from the internet
  • Recipient or person intended to read the e-mail
  • email flow chart


Note: There are numerous factors outside of RDP that can effect whether or not the recipient receives an e-mail. RDP only starts the process as the author (see diagram above) and cannot guarantee the e-mail will be received. However, this document is designed to help troubleshoot and configure RDP to deliver the e-mail to the SMTP (Simple Mail Transfer Protocol) server and to make sure the SMTP server is able to send the e-mail out to the internet.



Installation and Configuration Steps
  1. SMTP & E-Mail Server Options
  2. Requirements for SMTP Server
  3. Verify SMTP Server is Installed
  4. Restrict SMTP Access by IP Address
  5. Restrict SMTP Relay by IP Address
  6. Change Message Parameters in SMTP
  7. Open Port 25 for Sending and Close Port 25 for Receiving on the Firewall
  8. Send Test E-Mail with RDPWin
  9. Test SMTP Server with Outlook Express

E-Mail Troubleshooting Guide
  1. Possible Reasons E-Mail is Bounced or Rejected by Receiving Server (SPAM)
  2. Test with MX Tools
  3. Test Authentication with Telnet
  4. SMTP Server Troubleshooting Tips

1. SMTP & E-Mail Server Options

Whenever e-mail is sent from RDPWin or the IRM.Net it must first go to an SMTP e-mail server.  Customers have the option to use Microsoft SMTP server, ISP (Internet Service Provider) based SMTP server, or other e-mail server like Microsoft Exchange.

WARNING: RDP software enables the use of ISP based SMTP servers or other e-mail exchange servers. However, RDP Support is not responsible for supporting these configurations because they require a third party such as an ISP. RDP recommends using Microsoft SMTP server installed on the IRM server or RDP data server.

SMTP Server Type Explanation and RDP Support
Microsoft SMTP Server  Microsoft provides a SMTP server with every copy of Windows 2003 and 2008 server.  This is the recommended method 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"
ISP based SMTP Server 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, some ISPs will not allow a third party program like RDP to send e-mail using their SMTP server because of concerns about spam and viruses.   If your ISP does not allow RDP to send e-mails, use the Microsoft SMTP server on either the IRM server or RDP data server.
Microsoft Exchange or
other E-mail Server 
Many customers already have an e-mail server, such as Microsoft Exchange, set up for use for outgoing e-mail.  The RDP software will allow e-mail sent using an e-mail exchange server. However, since there are over 100 different e-mail servers with different configurations, it is not possible for RDP to support Exchange or any other e-mail server.   Support of this configuration must be obtained from a third party and is not provided by RDP Support.

 2. Requirements for SMTP Server

The following steps are required for the SMTP Server:

Step Explanation
1. Windows 2003 or 2008 Server A Windows Server 2003 or 2008 with IIS 5.0 or higher is required to run the SMTP server. 
2. Registered Domain Name A registered domain name if often required to pass many spam tests.  
3. Static External IP Address Purchase an external static IP address from your Internet Service Provider (ISP).   When purchasing the static IP, inform your ISP that the intent is to use this IP address to host a website (IRM), and that e-mails are to be sent from this website.   
4. FQDN
Fully Qualified Domain Name
Every external internet address must have a fully qualified domain name (FQDN), such as IRM.Resortdata.com.
5. Forward Lookup

DNS "A" Record 

The forward DNS lookup associates the Fully Qualified Domain Name to the external IP address.  For example,  the FQDN of IRM.Resortdata.com has a forward DNS lookup to 65.38.150.7. Contact your IT person to set up forward lookup.

6. Reverse Lookup

DNS PTR Record

Required so E-Mail 
is not treated as spam

Spam filters have become much more aggressive in recent years and more e-mail is treated as spam than ever before.  If your e-mail is treated as spam, it may be caught in a spam filter and never gets to the recipient.  Set up your SMTP server so that e-mail sent has the greatest possibility of not being treated as spam. 

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.
7. SSL Certificate

 

A Security Certificate (SSL) is not required to send e-mail.  However, many customers purchase one for their IRM or IRM.Net. IRM.Net version 3 requires the SSL to be installed. The common name of the SSL must be the Fully Qualified Domain Name.   For example, IRM.Resortdata.com.  See "Ordering and Installing a Security Certificate."
8. Firewall Changes Changes to firewall are required to send e-mail. These changes include:
  • 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."

9. Setup SMTP Server Set up the SMTP server on the Windows Server 2003 or 2008 with the steps in the remainder of this document.

3. Verify SMTP Server is Installed

RDP suggests using the Microsoft SMTP e-mail server installed on the IRM or RDP data server. To verify if the SMTP service is already installed:

  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 --> Administrative Tools -->  Internet Information Services (IIS).
  3. If SMTP is installed, it should appear similar to the diagram below.  If not installed, see IRM Installation Document - Customer Steps.

4. Restrict SMTP Access by IP Address

After the SMTP server is installed, configure to allow access from all workstations and restrict access from outside computers, so that an unauthorized individual cannot send spam through your SMTP server.  There are many security techniques available. However, RDP only supports restricting access to the SMTP server by IP address, as follows:

  1. From the Windows Server 2003 or 2008 that has SMTP installed, login as the administrator.
  2. Select Start --> Programs --> Administrative Tools --> Internet Information Services (IIS).
  3. Highlight the Default SMTP Virtual Server -->  right click --> select Properties.
  4. Select the Access tab --> click the Connection button.  
  5. Select the Only the List Below radio button --> click the Add button. 
  6. Select the Group of Computers radio button -->  enter the Subnet address --> enter the Subnet mask.  In the example, the Subnet address is 192.168.43.0 and the Subnet mask is 255.255.255.0. This 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, reboot the server before testing e-mail.

5. Restrict SMTP Relay by IP Address

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

  1. From the Windows Server 2003 or 2008 that has SMTP installed, login as the administrator.
  2. Select Start --> Programs --> Administrative Tools --> Internet Information Services (IIS).
  3. Highlight the Default SMTP Virtual Server -->  right click --> select Properties.
  4. Select the Access tab --> click the Relay button.  
  5. Select the Only the List Below radio button --> click the Add button.  
  6. Select the Group of Computers radio button -->  enter the Subnet address --> enter the Subnet mask.  In the example, the Subnet address is 192.168.43.0 and the Subnet mask is 255.255.255.0. This allows access for all computers from 192.168.43.1 to 192.168.43.255.
  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, reboot the server before testing the e-mail.

6. Change Message Parameters in SMTP

Change the Parameters for Messages in SMTP as follows:

  1. From the Windows Server 2003 or 2008 that has SMTP installed, login as the administrator.
  2. Select Start --> Programs --> Administrative Tools --> Internet Information Services (IIS).
  3. Highlight the Default SMTP Virtual Server --> right click --> select Properties.
  4. Select the Messages tab.  
  5. Remove the checks from each box. 
  6. In the Send Copy of Non-Delivery Reports to field, add the e-mail address of someone at your company who should be notified each time an e-mail message cannot be delivered. 
  7. Click OK.

7. Open Port 25 for Sending and Close Port 25 for Receiving on the Firewall

Change the 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. Close port 25 for receiving.

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

8. Send Test E-mail with RDPWin

The most important step in determining why e-mails sent from RDPWin are not delivered is to make sure RDPWin is able to communicate with the SMTP server. RDPWin is NOT a SMTP server. Instead it uses an internal or external SMTP server to send e-mails.

If RDPWin is not configured to use SMTP, e-mails will not be sent. The steps below are designed to make sure RDPWin (author) can communicate with the SMTP server (sender). This is similar to making sure an envelope (RDPWin e-mail) is addressed correctly and placed in the mailbox for the postman (SMTP server) to pick up. RDPWin is not responsible for the letter actually making into the recipients hands.

  1. In RDPWin, go to the Reporter main menu --> Configuration --> E-mail tab.
  2. Verify or enter the SMTP server in the SMTP Server field.
    • The SMTP server can be internal (inside your network) or external (i.e. google, hotmail, or other hosted e-mail server).
    • Use an IP address, the server name, or an URL to an external SMTP server. 
  3. If the SMTP server requires authentication, enter the credentials in the SMTP Logon field and SMTP Password field.
  4. Enter a valid from address in the Default 'From' E-Mail Address field.
  5. Enter a valid address to send a test e-mail in the Send Test E-Mail To field.  
  6. Click Send Test E-mail.
  7. Email Configuration 

  8. If RDPWin is communicating with the SMTP server, the following dialog box appears:
  9. Email Info


If RDPWin returns an error message after the Send Test E-mail button clicked, see the table below:

Error Message Solution

A Connection attempt failed because the connected party did not properly respond after a period of time, or established connected failed because connected host has failed to respond 192.168.43.8:25

  • Verify that the SMTP server address is correct in RDPWin --> Reporter --> Configuration --> E-mail tab --> SMTP Server field.
  • Verify the SMTP server is turned on.
  • If using external mail server, ping the server and make sure a reply is received.

No connection could be made because the target machine actively refused it 192.168.43.7:25

  • Verify that the SMTP server address is correct in RDPWin --> Reporter --> Configuration --> E-mail tab --> SMTP Server field.
  • Verify the SMTP server is turned on.
  • If using external mail server, ping the server and make sure a reply is received.

Mailbox unavailable. The server response was: 5.7.1 Unable to relay for sysadmin@resortdata.com (Trace: EMailConfig-btnSend)

No response from Mail Server

No such host is known

  • If using authentication and you receive this message, verify that the SMTP server is correct in RDPWin --> Reporter --> Configuration --> E-Mail Tab --> SMTP Server field.
  • See Testing External SMTP with Telnet.

Mailbox unavailable. The server response was: <test@hotmail.com> No such user here (Trace:EMailConfig-btnSend)

  • If using authentication and receive this message, verify that the user name and password are correct in RDPWin --> Reporter --> Configuration --> E-Mail tab --> SMTP Logon and SMTP Password fields.
  • See Testing External SMTP with Telnet.

9. Test SMTP Server with Outlook Express

There are many reasons why an e-mail is not received successfully. It is not possible for RDP to troubleshoot all possibilities.  If the e-mail is not received, use the procedure below to test using Microsoft tools.  If the e-mail is still not received, have your IT person call Microsoft Support, since the problem will be isolated to Microsoft products only.

  1. Install Outlook Express on the IRM 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. Use 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 Outlook Express successfully sends the e-mail through the SMTP server then RDP will also work.
Field Setting
Incoming E-Mail (POP3) Set the incoming SMTP server to "test@test.com" because there is no incoming e-mail in this test.
Outgoing E-Mail (SMTP) The SMTP server must be the IP address of the Windows Server 2003 or 2008,  XP, Vista, or Windows 7 computer 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.  Use a 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.  Use an account named "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. 

E-Mail Troubleshooting Guide

Possible Reasons E-Mail is Bounced or Rejected by Receiving Server (SPAM)

  • Blacklisted
    • Spamhaus is responsible for three widely used anti-spam DNS Blocklists (DNSBL): Spamhaus Block List (PBL), Exploits Block Lists
      (XBL), and Policy Block List (PBL). Many ISPs use these services to reduce the amount of spam.
  • Temporary Rejection or Grey Listed
    • Grey listing is the technique to temporarily reject messages from unknown sender mail servers. A temporary rejection is designated with a 4xx error code and then delivery is retried later.
  • No e-mail account
    • If the SMTP server finds that the destination is incorrect or that the mail account be delivered, it constructs an "undeliverable mail" notification message and sends it back to the sender.
    • Silently drops messages.
  • Reverse DNS Lookup returns a "no domain associated" message. The e-mail will likely be deleted, filtered, or bounce to the sender.
    • Setup and test reverse lookup.
    • Configure e-mail address to receive a copy of the non-delivery report.

Test with MX Toolbox

MX Toolbox is used to test if your SMTP is blacklisted, if the MX record exists, and tests DNS.

  1. Go to mxtoolbox.com.
  2. Enter your Domain Name (i.e. resortdata.com) and click the MX Lookup button.
  3. Click the links for SMTP Test, Blacklist Check, and DNS Lookup. Verify if the tests pass.

Test Authentication with Telnet

The telnet commands allow you to communicate with a remote computer using the Telnet protocol.  Use telnet to test to see if the authentication is sucessful for SMTP servers that require authentication.

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:

  • Always test with Microsoft Outlook Express. Using this program confines the problem to Microsoft products, allowing you to receive support directly from Microsoft.  Generally speaking, if Outlook Express works, so will RDPWin.
  • While RDP suggests using Windows Server 2003 or 2008 as the SMTP server, in a peer-to-peer environment without a server, a Windows XP Professional, Vista, or Windows 7 workstations 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 firewall can also stop e-mail.  In this case, the test e-mail will appear to work, but the e-mail is never received.  See Open Port 25  for more information.
  • 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 on the SMTP server computer.  See SMTP Folders Incorrect.

E-Mail Related Topics

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