Cannot e-mail monitor alerts from windows server 2003

Hi,

I have a windows server 2003 not running exchange. I have backup software that I want to receive status and alert messages via e-mail to an external e-mail account. I have setup the e-mail notification configuration in the backup software and the w2k3 event log says it cannot be delivered. The PC clients in the domain run outlook (e-mail server on external server) and can send and receive e-mail without issue.

Do I have to install/setup an account on smtp server on the w2k3 system to allow the emails from the monitoring clients (like backup software) to be able to send reliably?
DennisHebertAsked:
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SembeeConnect With a Mentor Commented:
If the tool that you are using to send the email doesn't keep a copy of the message then there is very little that you can do. You cannot see that the message has gone anywhere other than the SMTP logs.
If it was McAfee that was blocking SMTP traffic then you might have better success using the ISPs SMTP server instead.

Simon.
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SembeeCommented:
If you want to send email to an external account then you have to configure relaying. Allowing anonymous accounts to relay is a bad idea, that is an open relay.

You have a number of options.

1. Authenticate. If the tool that is going to send the emails can authenticate when it sends, create an account for that application to send email.
2. Look at your relaying settings to allow the server to relay email by IP address. I don't like this option as it can be easily abused.
3. Use another server. This is my preferred method. I will send email messages through the ISPs SMTP server, even if there are mixed internal and external users. Internal email will come back in and external will be delivered in the usual way.

Simon.
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DennisHebertAuthor Commented:
Simon,

Thanks for your reply. I am not sure if I am doing #1 correctly, but I listed the admin username in the backup application and it did not send email. I also configured the email server to be my isp's server...no change.

I don't know where the relay settings are???

Thanks
Den
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SembeeCommented:
The relay settings are in IIS Manager, SMTP, Protocols, SMTP. Right click on the SMTP VS and choose Properties. Click on the tab Access and then Relay.

However, if using the ISPs SMTP Server doesn't work, then I would have to question whether the alerts are being sent at all.
Can you telnet to the ISPs SMTP server on port 25?

telnet mail.isp.net 25

If not, then that would explain why it isn't working.  

Simon.
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DennisHebertAuthor Commented:
Simon,

The SMTP VS has relay setup from the server only.

When I try telnet...it cannot access the isp smtp server.

The w2k3 does not have firewall or nat installed. This service is being done at the firewall/router. I checked the tcp/ip filtering and there are no filters in place.

Thanks
Den
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SembeeCommented:
If you cannot connect to the ISPs SMTP Server then port 25 is being blocked somewhere. I would doubt if the ISP is blocking it as most ISPs want you to send email through their server rather than directly. Therefore there has to be some kind of block locally.

Simon.
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DennisHebertAuthor Commented:
Simon,

The McAfee security software was blocking port 25. I opened this up and now I can telnet to the smtp server, but the alert emails are not being sent or delivered. I checked my email server to see if it was auto blocking the email and they are not.

I looked at the log on the router and can see outgoing smtp from the w2k3 server, so it seems like it is going out. Is there a way I can "see" the email that was sent?

Thanks
Den
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