SMTP cleanup and maintenance 1

[wahnula]

Hello,

I recently received a series of warnings regarding many messages in my SMTP queue. I noticed many were from postmaster@myserver.com so I followed the instruction here:

http://support.microsoft.com/?kbid=886208

When I followed these instructions, my users received hundreds of old messages that had not been sent as well as non-deliverable mail messages.

Question: Should that operation from kb 886208 be all I need or do I need to block open SMTP relaying:

http://support.microsoft.com/kb/324958

In addition to the previous action? Thanks!

Tony

 

[ShackDaddy]

Which step did you follow in that first article?

ShackDaddy
Shackelford Consulting

 

[wahnula]

Which step did you follow in that first article?

Shackdaddy,

I followed all three steps, but did not have to create a "temporary SMTP connector". Since I had modified the SBS SMTP connector that was there I deleted it (after step 3) and re-added it manually. Mail seems to be moving normally and all the queues seem to be empty. There were 960 messages in the queue before I implemented the first article.

Tony

 

[wahnula]

Here's a screenshot of my queues:

http://www.tonyandterri.com/smtp.jpg

It shows a message being "stuck" that is a legitimate message from an employee to a customer. Since I am using Exchange for email do I even need this "sbs smtp connector"?

Thanks

 

[ShackDaddy]

Don't delete that connector. It's basically the engine that routes mail out through your other SMTP Virtual Server. It's an essential part of Exchange functionality.

The "stuck" message is probably just greylisted, which means that as an anti-spam measure, the receiving server asked the sending server to wait X number of hours before attempting a re-delivery. It will probably eventually make it through.

ShackDaddy
Shackelford Consulting

 

[wahnula]

Thanks ShackDaddy. I'm out of my bailiwick once I leave the wizards!

What about blocking open SMTP relaying as in the second article posted above to prevent future problems? Thanks for your time.

Tony

 

[ShackDaddy]

By default open relay is blocked, so if you haven't messed with it, you shouldn't need to worry about it.

ShackDaddy
Shackelford Consulting

 

[wahnula]

OK Shackdaddy. That message is still in the queue, I've told the user and had him re-send.

Thanks as always.

Tony

 

[ShackDaddy]

Ok. Typically no need to actually resend from the mail client. The server just holds it in queue and reattempts delivery after an extended period of time.

ShackDaddy
Shackelford Consulting

 

[wahnula]

Hmmm....I just got this from a user:

The following recipient(s) could not be reached:

  xxxxxx@hotmail.com on 9/26/2007 12:55 PM
  There was a SMTP communication problem with the recipient's email server.  Please contact your system administrator.
  <lynnslandscaping.com #5.5.0 smtp;550 Your e-mail was rejected for policy reasons on this gateway.  Reasons for rejection may be related to content with spam-like characteristics or IP/domain reputation problems.  If you are not an e-mail/network admin please contact your E-mail/Internet Service Provider for help.

Is this anything I need to be concerned about? It only happens with this one user, maybe a pebcak or Outlook problem? lynnslandscaping.com is our company.

BTW you were right the queues are all empty.

Tony

 

[ShackDaddy]

Just hope it was content. I work with a big 3rd-party spam scrubbing operation, and last week they got on the Microsoft services blacklist and we were seeing thes messages from msn.com and hotmail.com and live.com mailboxes. If it continues to happen and occurs with more than just this user, you'll probably want to go to the hotmail site and dig around for your options as far as getting off their blacklist. Sometimes you can't, if, for example, your IP address is in a block of addresses that they won't accept mail from. Then you have to build an extra custom connector in Exchange and route mail to them through your ISP smarthost...

ShackDaddy
Shackelford Consulting

 

[wahnula]

I agree about the content. We have been blacklisted before as our website has a published info@address with an autoresponder that leads to a ton of spam, and our autoresponder gives the spammers an active address so I'm sure we're doomed. I've had our domain go to spam folders many, many times. It would not be that hard to circumvent as the way I have things set up now lynnslandscaping.com forwards all email to the server's TZO address (servername.com), I could simply use that address as our main email address, or sub the

http://www.lynns.ws

domain we own for the old one in Exchange...just a PITA.

Tony

 

[ShackDaddy]

The main reason you are likely to get blocked as spam is that it sounds like your sending mail server address isn't static, and because of that you aren't able to maintain an RDNS record. Is that true?

ShackDaddy
Shackelford Consulting

 

[wahnula]

No. Sending SMTP server is static, tied to the website.

Tony

 

[ShackDaddy]

Ok. I was just unsure of what role TZO was playing.

ShackDaddy
Shackelford Consulting