# ActionMailer e-mails getting tagged as junk in Outlook 2003 **URL:** \ **Category:** Rails\ **Created:** [March 30, 2006, 7:48pm UTC](https://www.ruby-forum.com/t/actionmailer-e-mails-getting-tagged-as-junk-in-outlook-2003/56386 "2006-03-30T19:48:00Z")\ **Posts on this page:** 5\ **Page:** 1
**Author:** ![dmarkow](https://www.ruby-forum.com/letter_avatar_proxy/v4/letter/d/bc8723/32.png) [@dmarkow](https://www.ruby-forum.com/u/dmarkow)\ **Post date:** [March 30, 2006, 7:48pm UTC](https://www.ruby-forum.com/t/actionmailer-e-mails-getting-tagged-as-junk-in-outlook-2003/56386/1 "2006-03-30T19:48:00Z")
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! ---
**Author:** ![dmarkow](https://www.ruby-forum.com/letter_avatar_proxy/v4/letter/d/bc8723/32.png) [@dmarkow](https://www.ruby-forum.com/u/dmarkow)\ **Post date:** [March 30, 2006, 8:48pm UTC](https://www.ruby-forum.com/t/actionmailer-e-mails-getting-tagged-as-junk-in-outlook-2003/56386/2 "2006-03-30T20:48:59Z")
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? ---
**Author:** ![dmarkow](https://www.ruby-forum.com/letter_avatar_proxy/v4/letter/d/bc8723/32.png) [@dmarkow](https://www.ruby-forum.com/u/dmarkow)\ **Post date:** [March 30, 2006, 9:16pm UTC](https://www.ruby-forum.com/t/actionmailer-e-mails-getting-tagged-as-junk-in-outlook-2003/56386/3 "2006-03-30T21:16:30Z")
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? ---
**Author:** ![dmarkow](https://www.ruby-forum.com/letter_avatar_proxy/v4/letter/d/bc8723/32.png) [@dmarkow](https://www.ruby-forum.com/u/dmarkow)\ **Post date:** [March 30, 2006, 10:39pm UTC](https://www.ruby-forum.com/t/actionmailer-e-mails-getting-tagged-as-junk-in-outlook-2003/56386/4 "2006-03-30T22:39:32Z")
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 ---
**Author:** ![dmarkow](https://www.ruby-forum.com/letter_avatar_proxy/v4/letter/d/bc8723/32.png) [@dmarkow](https://www.ruby-forum.com/u/dmarkow)\ **Post date:** [March 30, 2006, 11:00pm UTC](https://www.ruby-forum.com/t/actionmailer-e-mails-getting-tagged-as-junk-in-outlook-2003/56386/5 "2006-03-30T23:00:50Z")
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](http://www.openspf.org/wizard.html) …and I use this to test with: [http://www.seoconsultants.com/tools/spf/](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 > **[Tree Removal Service For Home & Businesses in Salt Lake City, UT](https://www.rentamonkey.com/)** > > Rent A Monkey Tree Service provides the safest, highest-quality tree removal for Salt Lake City, UT homes and businesses. Request a service today! PGP Key: [http://www.rentamonkey.com/pgpkey.asc](http://www.rentamonkey.com/pgpkey.asc)