Outgoing Email and Messagelabs

Hello, I wanted to setup a secondary backup server to be able to send outgoing emails.

I have it all up and running, and working. Now I just need to direct our emails to Messagelabs (for spam/AV/reporting). Messagelabs will only accept emails from our external IP address (203.x.x.x)

When I look at the header information of an email, it shows the source ip address as the internal ip address of the exchange server. And Messagelabs returns the email saying that it wont relay emails from this IP address.

I dont know if this is an exchange setting, windows networking setting, or a Cisco router setting.

Is anyone able to tell me how to make our exchange server send emails with its external IP address settings in the email header rather than internal ones.


The server is sitting in the DMZ of our network with one NIC. (192.168.50.x)

Our ISA server routes traffic from the DMZ out to the external network.


Thanks,
Dekkar
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dekkarAsked:
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B HCommented:
are you telling the secondary server to send its mail THRU the primary server?  

that will generate the first (bottom) "received from" line, and that's what they're seeing.

if you can make your secondary server send it directly thru messagelabs thing, then the first received-from line will be your outside ip address*

*if your primary server is natting behind a different ip address than your secondary server is, then they will both appear as different ip addresses.   when you go to www.cmyip.com from the primary and secondary servers, are the ip addresses the same?  if not, stick them in the same zone (the one with the ip address you want)
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bluebookCommented:
[I work for MessageLabs]

MessageLabs does not look at the IP addresses in headers to determine whether or not you are allowed to relay; as the previous poster suggested, the address we are interested in is the public IP address which you are natted to and from which we receive your connection.  It sounds like it is definitely different to the address that your primary server is natted to.  However, there is no need to change this (i.e. they do not both have to be the same) - you just have to tell MessageLabs about the second IP address.  You can do this through the management console at clients.messagelabs.com.  Click on the Configuration tab and select Outbound Routes from the Email Services menu.  Alternatively raise a ticket with support.

Paul
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B HCommented:
hi paul - as long as you're subscribed to this thread.... my company is looking for a solution to capture all outbound emails sent from our exchange server, in a searchable format, to make sure people aren't screwing off or giving away secrets... is that what messagelabs does?  i glanced at the site but there's way too much stuff there than i have time for
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dekkarAuthor Commented:
Hi.... yes Paul, Kind of correct.... it was the natting on the outward facing cisco router that handnt been configured.

Upon checking this, the new exch server was actually sending out on a legit external IP, one that our current exchange server was sending out on. Except there was no natting setup. So the email 'looked' like it was coming from our internal server. I dont really understand why...


I setup a nat from the new edge exchange server, to one of our spare external addresses, and then added this address to the list of accpeted IPs in ML...


Now the header information on the emails looks good. And MLabs are sending our emails correctly!


Thanks,
Dekkar
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bluebookCommented:
bryon: Yes that is one of the services we provide; actually there are 2 related ones:
- Content Control, which allows you to implement DLP by blocking and / or monitoring based on email content
- Archiving, which captures every message and allows you to search across all of them by content, sneder. recipient, etc.
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dekkarAuthor Commented:
Byron, just know that although its in a searchable format, you cant search the content of the email, only subject lines and senders.

Also the search only goes back 1 month. So if you want to find something older than that, you will have to go back to your own exchange records.
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bluebookCommented:
Actually that's not quite true...  There is a standard feature called Track&Trace which you get with any of the MessageLabs email services, which does behave exactly as you say.  But what I was referring to is the email archiving service, which allows you to search the body of emails and all attachments as well, and goes back up to 7 years IIRC - certainly multiple years anyway.
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dekkarAuthor Commented:
Ahhhh Archiving yes... We currently dont have that option.
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B HCommented:
where can i find good info about your archiving (with searching) function?  that's mostly what we're interested in, blocking messages from leaving based on content isn't as important as being able to prove what some joker told a client 2 years ago...
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B HCommented:
i'm looking for a link that i can give to our HR girl and say here, tell us if this is what you want (she's been asking for this) and if so we can buy it
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bluebookCommented:
Try this: http://www.messagelabs.com/products/archiving

We actually have a new alternate offering as well which is slightly lighter weight depending on your needs, but there doesn't seem to be a link to it yet.  A Sales guy would obviously be happy to talk you through both of them.
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