Rails - Mar 2006 - ActionMailer e-mails getting tagged as junk in Outlook 2003

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!

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?


On 3/30/06, Dylan Markow <dylan@dylanmarkow.com>
wrote:
>
> 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!
> _______________________________________________
> Rails mailing list
> Rails@lists.rubyonrails.org
> http://lists.rubyonrails.org/mailman/listinfo/rails
>
-------------- next part --------------
An HTML attachment was scrubbed...
URL:
http://wrath.rubyonrails.org/pipermail/rails/attachments/20060330/e91b6616/attachment.html

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?

Chris Hall wrote:
> 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?
>
>
> On 3/30/06, * Dylan Markow* <dylan@dylanmarkow.com 
> <mailto:dylan@dylanmarkow.com>> wrote:
>
>     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!
>     _______________________________________________
>     Rails mailing list
>     Rails@lists.rubyonrails.org <mailto:Rails@lists.rubyonrails.org>
>     http://lists.rubyonrails.org/mailman/listinfo/rails
>
>
> ------------------------------------------------------------------------
>
> _______________________________________________
> Rails mailing list
> Rails@lists.rubyonrails.org
> http://lists.rubyonrails.org/mailman/listinfo/rails
>   
-------------- next part --------------
An HTML attachment was scrubbed...
URL:
http://wrath.rubyonrails.org/pipermail/rails/attachments/20060330/3921212a/attachment-0001.html

On 30 Mar 2006, at 21:12, Dylan Markow 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

On Thursday 30 Mar 2006 20:12, Dylan Markow 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 Silvester
Rent-A-Monkey Website Development
http://www.rentamonkey.com/

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