ActionMailer e-mails getting tagged as junk in Outlook 2003

Rails
1

Whenever an email is sent via ActionMailer, and the recipient is using
Outlook 2003 (with SP2 installed), the e-mail is getting put in the junk
e-mail folder. Since Outlook doesn’t give a reason it was tagged as
junk, it’s hard to determine what to change.

I’ve compared the message headers of the “junk” mail and a valid email
sent through Outlook, and the headers are nearly identical. (I’ve even
tried tweaking the ActionMailer e-mail so that it is 100% identical, but
it still didn’t work).

The only thing I can possibly imagine is, since it’s a multipart (html
and plain text) message, that Outlook doesn’t like the way ActionMailer
splits up the MIME Parts??

Has anyone run into this before? I’m trying to create a marketing system
through our rails application, and the last thing I need is for all of
our Outlook recipients to not even see the e-mails.

Thanks!

2

wouldn’t this be an Outlook issue?

have you tried sending the emails to multiple recipients who use Outlook
to
see if the same behavior is exhibited?

3

I have tried it on several machines. The common factor seems to be
having Outlook’s SP2 installed, which supposedly has better
“anti-phishing” features. However, I don’t see why it would think the
e-mails coming from my rails server are being spoofed?

4

On 30 Mar 2006, at 21:12, Dylan M. wrote:

I have tried it on several machines. The common factor seems to be
having Outlook’s SP2 installed, which supposedly has better “anti-
phishing” features. However, I don’t see why it would think the e-
mails coming from my rails server are being spoofed?

Reverse DNS lookup failing? Because the machine you’re sending your
mail from (the relay server) is on a dynamic IP? I once tried PostFix
on my Powerbook, but quite a lot of servers denied my mail.

Best regards

Peter De Berdt

5

On Thursday 30 Mar 2006 20:12, Dylan M. wrote:

I have tried it on several machines. The common factor seems to be
having Outlook’s SP2 installed, which supposedly has better
“anti-phishing” features. However, I don’t see why it would think the
e-mails coming from my rails server are being spoofed?

I have no idea about Outlook (I don’t use Windows, let alone Outlook),
but
could it possibly be SPF records or similar? As far as I know, the
pass/fail
generally happens at mail server level, but I guess there’s no reason it
couldn’t happen in the client.

I tried a quick Google on “Outlook SP2 SPF” and it seems that Microsoft
are
starting to use something called “SenderID”, which based on 30 seconds
browsing appears to be the same as SPF.

SPF is probably not the culprit, but you might want to check your SPF
records
are correct anyway, just to be sure.

There’s an SPF setup wizard here (though it’s not hard to read up on how
they
work and roll your own):

http://www.openspf.org/wizard.html

…and I use this to test with:

http://www.seoconsultants.com/tools/spf/

Just a thought, since nobody else had mentioned it yet.

Cheers,

~Dave

–

Dave S.
Rent-A-Monkey Website Development

PGP Key: http://www.rentamonkey.com/pgpkey.asc