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SBS 2003 Send Email via Application

We have a customer that recently had GFI Vipre installed for AV. There is the possibility to setup email alerts, however, I have tried multiple things (messing with Relay, authentication, etc.) without success. This site is a single NIC SBS 2003 (no ISA). I am not great with Exchange, so I'm having trouble determining if somewhere SSL/TLS is enabled or enforced. But even with that, I have tried using proper AD credentials and the system still gives the error I will insert below. I checked the virtual SMTP server the IP address is set to "All Unassigned". Under Access > Authentication, "Anonymous Access" is checked but under Relay Restrictions, only the localhost (127.0.0.1) is allowed along with "Allow all computers which successfully authenticate to relay, regardless of the list above" being checked.

Scratching my head on this one. Any assistance is greatly appreciated. Thanks!

Error String in Vipre logs:

Verbose      29      2012-08-16T09:34:29      634807064690781250      Sending email with notification. To: Recipient@domain.com From: Sender@customerdomain.com Subject: VIPRE Site Service Test Email
Error      29      2012-08-16T09:34:29      634807064690781250      To: Recipient@domain.com, From:Sender@customerdomain.com, Server:10.0.0.2, Port:25, User:UserAccount
Enterprise.Arsenal.EmailController.SendMail( EmailServerSettingsXmlData String String Boolean )+529
System.Net.Mail.SmtpException: Failure sending mail. ---> System.IO.IOException: Unable to read data from the transport connection: net_io_connectionclosed.
   at System.Net.Mail.SmtpReplyReaderFactory.ProcessRead(Byte[] buffer, Int32 offset, Int32 read, Boolean readLine)
   at System.Net.Mail.SmtpReplyReaderFactory.ReadLines(SmtpReplyReader caller, Boolean oneLine)
   at System.Net.Mail.SmtpReplyReaderFactory.ReadLine(SmtpReplyReader caller)
   at System.Net.Mail.SmtpConnection.GetConnection(String host, Int32 port)
   at System.Net.Mail.SmtpTransport.GetConnection(String host, Int32 port)
   at System.Net.Mail.SmtpClient.GetConnection()
   at System.Net.Mail.SmtpClient.Send(MailMessage message)
   --- End of inner exception stack trace ---
   at System.Net.Mail.SmtpClient.Send(MailMessage message)
   at Enterprise.Arsenal.EmailController.SendTheMailMessage(EmailServerSettingsXmlData ess, MailMessage mail)
   at Enterprise.Arsenal.EmailController.SendMail(EmailServerSettingsXmlData ess, String emailSubject, String emailBody, Boolean isBodyHtml)
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aaron_tr
Asked:
aaron_tr
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1 Solution
 
Sudeep SharmaTechnical DesignerCommented:
Did you try to communication from the Vipre system to Exchange using the telnet?

Command would be:
telnet exchange_IP_address 25

Did you get the connection? If not what errors do you get?

telnet command is not installed on Windows 7 or Windows 2008 by default so you would need to add it from Windows Feature from Control Panel --> Programs and Features.
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aaron_trAuthor Commented:
I did attempt telnet and it doesn't give a 220, it just takes me back to a command prompt. Just to be clear, the Vipre console is on the SBS box, so I am attempting to telnet to the localhost (telnet 10.0.0.2 25). I wasn't sure where I could modify the setting(s) to not reject/close that connection, that was part of the equation that eluded my understanding. I assumed that is where the issue lies, but wasn't sure how/where to correct that. Thanks.
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Sudeep SharmaTechnical DesignerCommented:
Authentication, "Anonymous Access" is checked but under Relay Restrictions, only the localhost (127.0.0.1)

Add the IP address of Vipre to this section.
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aaron_trAuthor Commented:
Vipre is installed on the SBS box (127.0.0.1). I did try adding 10.0.0.2 as well, but no change. Does it take time to update the policy (similar to recipient policies)?
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aaron_trAuthor Commented:
To clarify, the LAN IP of the SBS box is 10.0.0.2. So I left 127.0.0.1 in the Relay Restrictions, but also added 10.0.0.2. Then using "telnet 10.0.0.2 25" returns same result (returns to command prompt).
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Sudeep SharmaTechnical DesignerCommented:
Did you restarted the Transport Service?
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aaron_trAuthor Commented:
I did not. I will restart now and report back afterwards.
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aaron_trAuthor Commented:
Hmm...no MS Exchange Transport Service.

SBS 2003 lists the following:
Microsoft Exchange Event
Microsoft Exchange IMAP4
Microsoft Exchange Information Store
Microsoft Exchange Management
Microsoft Exchange MTA Stacks
Microsoft Exchange POP3
Microsoft Exchange Routing Engine
Microsoft Exchange Site Replication Service
Microsoft Exchange System Attendant

Like I stated, not very good w/ Exchange 2003. Is it named something different in 2003?
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Sudeep SharmaTechnical DesignerCommented:
May I ask if you have SMTP enabled on the Exchange?
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aaron_trAuthor Commented:
Yes. This is SBS 2003. All email works fine from clients like Outlook/ActiveSync, but Vipre can't send the email from its management console.
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aaron_trAuthor Commented:
So, I restarted the SBS box over the weekend, but no change. So, GFI Vipre's management console is installed on their SBS server (10.0.0.2). When I am logged onto the SBS box and attempt to telnet to port 25, it returns me to a command prompt (no EHLO or 220 response). I think that's the issue, but not sure where to start to allow that telnet traffic through (but without allowing the server to become an open relay). Any thoughts? Thanks.
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aaron_trAuthor Commented:
I have resolved the issue. Here was the resolution to allow Telnet to port 25 on the localhost:

Go into Microsoft Exchange System Manager > Servers > *servername* >  Protocols > SMTP > (right-click) Default SMTP Virtual Server > Properties > Click the "Access" Tab > Click "Connection" under the Connection Control section > add server IP (either 127.0.0.1 or LAN IP, in my case 10.0.0.2).
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aaron_trAuthor Commented:
After figuring out this issue on one SBS 2003 server, I found this worked on two other SBS servers where I had issues with local telnet to SMTP. Issues resolved.
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