Outlook 2007 Junk Email Filter

**richyrich** · richyrich, March 1st, 2010 09:01 AM

I've just taken over sending out marketing emails for the company and am finding that when I'm testing them, they keep appearing in Outlook Junk Email. Previously the guy sending them had very few issues with this. The company does sell chemicals, but not like the "prescription drug" emails that get picked up as spam all the time. The drugs are for research purposes.

In Outlook it says "This message was marked as spam using the Outlook Junk Email filter". If I send to a gmail or live (hotmail) address it appears in the inbox fine.

I re-wrote the original HTML email template as there were a few discrepancies with it (2 <body> tags, for example) the previous guy used DreamWeaver to edit the templates. I'm just using Notepad.

Also, for some bizarre reason, if I send exactly the same email with the subject line "Order before December 14th for prize draw", the email appears in the Inbox. I don't think there's anyway of marking a specific subject as not spam ie, I couldn't have previously marked just the subject as not spam so any messages with that subject aren't junked. I've tried various different subject lines and they've all gone into Junk.

I've checked the email using an online content checker and it comes back with a low score (0.2) and I've checked the content against the supposed spam words the Junk filter looks for on Microsoft's website and it seems this email doesn't contain any of the word combinations they list.

I've also checked the mail servers on blacklists and they all come back as not blacklisted. I'm sending it through my own mail server that has reverse DNS setup correctly on it.

Any ideas what might be causing the emails to be flagged as Junk by Outlook?

On the previous email, I thought I had narrowed it down to the number of links in the email. If I added one more link, it went into Junk. The current email has less links than the previous one, so I can't see it could be that.

At the moment I have no idea what might be causing the Junk Filter to pick up on these emails. Anyone have any ideas of what I can try?

Current things I've tried changing:-
1) The subject
2) Removing all the links.
3) Changing the first 2 paragraphs of the email to just normal text.
4) Removing a table that contains 3 links to the website.
5) Removing any chemical names from the email.

I could keep testing till the cows come home but without knowing what might be causing the problem, it's difficult to know where to start.

**Kraevin** · Kraevin, March 5th, 2010 03:37 PM

First thing I would check is that the from email address is from the same domain as the server they are being sent from.
If you send from nospam@wearenotspammers.com but the server is wearenaughtyspammers.com then outlook is likely to flag it. Especially if the nslookup for the 2 domains are different ip's.
Also any scripting that tries to redirect or get dynamic content.

**richyrich** · richyrich, March 5th, 2010 03:50 PM

I have been testing them in various environments. One email marketing software package uses a mail account designed to send email campaigns. this account is different from the actual domain name, but uses an SPF record to allow sending from particular IPs.

I have also tried through my own VPS server using my own domain / email. The VPS has it's own IP with RDNS and the DNS has an SPF record allowing sending of emails for the specific domain.

Also none of the domains or servers are blacklisted.

If I send to a google account, the SPF header gives a PASS rating from google. I don't seem to have an issue with any spam software or mail servers, it's just when it is retrieved by Outlook and goes through the Junk Email filter.

I do seem to have resolved some of the issues, although still really none the wiser as to what the problem is. One of the test users still gets the email in her Junk Email but myself and 2 others receive it in our Inbox. All of us are on the same domain and receive the same email from the email marketing software through the same mail account.

Very odd.

**Kraevin** · Kraevin, March 5th, 2010 04:00 PM

What are the differences?
Are the test accts all on the same version of outlook, and the same email server?

**richyrich** · richyrich, March 5th, 2010 04:12 PM

Yes. They all run on Outlook 2007. All emails are on the same domain through the same email server.

All have the same setting on the Junk Email Options (Low).

Another quite strange thing happened yesterday when I was testing through my own server. When one of them sent a normal, unrelated, email from Outlook to a different email address of mine, when I received it, it went into my Junk Email in Outlook 2003. He then sent me another email, with a screenshot included in it, and that went into my Inbox.

All the tests I tried today went into the Inbox of 3 out of 4. Just annoying that I can't figure out what is causing the other machine to Junk them. I know the email virus checker is disabled on her machine as well, because it was causing Outlook to crash.

**Kraevin** · Kraevin, March 5th, 2010 05:11 PM

Well If i was bound to find out I would take a methodical approach to it.

I would set up a machine using outlook and send the email in the same format as what the server is. If that junks it you know its content and can test from there cutting things out.
If not then try to set up another computer to access the test email account and see if that junks it. If it doesnt then its probably something in the setting on that computer.

If it does then probably something with the way its being sent. Could be many differnt things you can try and tweak the settings to see if you can get it to pass and figure it out.

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