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Troubleshooting spam

Running Exchange 2007 with Symantec Mail Security and Premium Antispam.  Is there any way through logging or SMS of troubleshooting exactly why a message was flagged as spam so we can instruct users on composing emails or find out if it was due to another reason that it was flagged?  If not is there a tool out there somewhere that you can run an email through to see if something in it causes it to be suspected spam?  We have a network of business peers and occasionally someone's message doesn't get through.  I'd like to be able to tell them why something got flagged instead of just that it got flagged for some reason.
2 Solutions
Rodney BarnhardtServer AdministratorCommented:
I don't think there is a good tool for this option. Many times, the block is on the receivers side and it could be the way they configured their spam filter. I know I have worked for companies where we manually added key words to block. Later, some of those had to be removed because is kept a lot of legit email from coming through.

As an example, my fathe-in-law works in sales. He was trying to get an email through to a specific client, who requested information. When he finally spoke with the clients IT person, the guy told him to remove the word "free" from his email subject line. They were blocking all emails with the subject "free" in it.

Even where I work now, we are asked by users to add key words, domains, senders, etc to the "black\block list". So, I don't think you are going to find a way to always explain why an email was blocked.
To see if you ended up on a spam list, just google email blacklist, for example, you'll see lots of them. ALot of these lists are automated, so removing yourself is pretty much impossible. That said, if you aren't a frequent violator, you'll drop off the list in a few days automatically.

In my experience:
about 1/2 of all "spam issues", defined as someone thinks their email they sent out is being treated as spam, is due to a wrong email address. User error, not a spam issue.
The rest of the time, that email is being treated as spam for a number of reasons:
1. There are components of the message that make it appear to be spam (too many recipients, lots of links to crap sites, vulgar language, etc...). Spam filters weigh each message and decide how likely a message is spam based upon a scale. The more parts that fit that profile, the more likely it will be tagged as spam.
2. Your email domain is a known spammer, or your website has been blocked as a security risk and the emails were wrapped up in that blocking. It does happen. If your website is hosted by a unsavory webhost (hostgator comes to mind as I've had to deal with this and they ended up as the reason for the issue), then you run that risk.
3. Your ISP is a haven for spammers, or allows spammers to send email out their pipe. Time Warner, Knology, Comcast, Deltacom, etc have all had this problem at times. Think about it. lots of infected home pc's (spam bots) churning away and spewing millions of spam messages. The big boys are going to refuse their traffic until they clean up their act.
4. Newsletter unsubscribes. If you mail out marketing info to people regularly, you will end up on a spam list, even if you do everything right. This is because people are lazy, and may tag your emails as spam (or the marketing departments emails) instead of using the unsubscribe feature, thus ruining it for everyone sending mail from your domain.
5. Your domain records don't match the email server address. Add a SPF entry in your domain records so that you're domain is more trustworthy. I'm not sure of the exact mechanics in play here.
In summation, to prevent this long term: Hook up with a good third party spam filter that filters in and outbound. If you must use email marketing, setup a separate domain and mail system to send outbound, and managed the lists and unsubscribes properly. Use a reputable ISP. Get a good webhost, not the cheapest one.
Brian_MBAuthor Commented:
Thanks guys, I just wish ther was a tool to "run" an email through to see why it might have a problem.  Or at least it'd be nice if you were able to find out why your own spam filter (symantec etc) blocked the email.  

t0dd_sw, lots of good info there.
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