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Classed as Spam by Large-Scale Free Email Servers?

bartle asks: "I run my own personal domain that serves all of my email needs of myself and a few friends. In general this has worked out pretty well but there's a fairly significant limitation: if I send an email to a Hotmail or Yahoo account that I've never contacted before it tends to get filed as spam. This means that if I'm writing someone out of the blue I need to send an email from a free service which kind of defeats the purpose of running ones own email server. My domain has a SPF record, the IP resolves, and it doesn't appear to be on any blacklists. I can not find any documentation on what hoops I need to jump through before Hotmail and Yahoo will consider my mail legitimate. I understand that there's a general paranoia about publishing information that could assist spammers but this attitude seems to be leaving do-it-yourselfers out in the cold. Does anybody have any ideas? Are there guidelines or protocols I can follow to make my email non-spam?"

9 of 86 comments (clear)

  1. I've run 2 ISP's, starting my third... by numbski · · Score: 3, Informative

    You're on a dynamic IP address, aren't you?

    Most major mail provider bl dynamic IP's. The way around this is to smarthost against a known, static-IP mail server. In short, smarthost outbound mail. Inbound mail is fine, and you'll be all fixed up.

    Not flaming you, but any good smtp faq or mailing list would have told you this, and Sendmail's FAQ answered it for me 3 years ago. :\

    Just wondering how we get to an ask slashdot from a simple mail administration question. Google really *would* have answered this.

    I know, I know, I'm new here. Next meme. :P

    --

    Karma: Chameleon (mostly due to the fact that you come and go).

    1. Re:I've run 2 ISP's, starting my third... by alienw · · Score: 4, Informative

      $ host chrisbartle.com
      chrisbartle.com has address 216.17.137.189

      $ host 216.17.137.189
      189.137.17.216.in-addr.arpa domain name pointer bartle189.dsl.frii.net.

      It may not be a static IP, but it's obviously an end-user address, and free services aren't too picky about who they block. I bet anything that has .dsl. in the reverse DNS is blocked.

  2. PTR DNS record by ttfkam · · Score: 4, Informative

    Likely it's because when the other end does a reverse DNS record lookup, and your hostname and the PTR record don't match up. Usually this ends up resulting in receiving fine but problems sending.

    Try setting up your ISP's SMTP server as your outgoing mail relay. In other words, when you send mail to your SMTP server, instead of looking up the remote host, doing an MX record lookup, etc., just send to your ISP's SMTP server. They should be configured to accept anything from your IP (you are their customer after all), and it only requires one extra hop for your email on the way out the door.

    Instead of:

    Email client -> Your SMTP -> MX record lookup -> Destination

    it becomes

    Email client -> Your SMTP -> ISP SMTP -> MX record lookup -> Destination

    After doing this, from your point of view, nothing will have changed, and you can learn to sysadmin on a small scale to your heart's content.

    A lot easier than getting an ISP to change the PTR record to your hostname.

    --

    - I don't need to go outside, my CRT tan'll do me just fine.
    1. Re:PTR DNS record by nmos · · Score: 2, Informative

      Try setting up your ISP's SMTP server as your outgoing mail relay. In other words, when you send mail to your SMTP server, instead of looking up the remote host, doing an MX record lookup, etc., just send to your ISP's SMTP server. They should be configured to accept anything from your IP

      That's certianly worth a try but some ISPs have their smtp servers set up to only relay mail with From headers that match one of their own domains so they might reject him anyway.

  3. to clarify by samjam · · Score: 2, Informative

    I htink that you are saying that the name as given in the SMTP HELO statement does not match reverse DNS.

    The HELO name usually defaults to the hostname.

    This implies if the guy can get his box to HELO with what the IP resolves to he will be OK.

    I'm just clarifying what I think you are saying to make the next step obvious.

    Sam

  4. That's not what you think it is. by khasim · · Score: 3, Informative
    In your original statement, you said:
    My domain has a SPF record, the IP resolves, and it doesn't appear to be on any blacklists.
    So ....

    chrisbartle.com resolves to 216.17.137.189

    but

    216.17.137.189 resolves to bartle189.dsl.frii.net

    So it doesn't resolve correctly. You might think you have a "static" IP address, but it appears the same as any other, dynamic, home DSL address.

    Unless you can get frii.net to change their DNS entry for you, you'll continue to have your mail rejected.
  5. Re:Followup by Bronster · · Score: 2, Informative

    The second suggestion is good and one I can probably implement in short order. I think I can talk my ISP into letting me manage my tiny block of IPs or at least changing what they resolve to. Someone pointed out that Hotmail spam script might just be looking for the term "dsl" and blocking based on that. It sounds stupid but in a very plausible way.

    The problem is that it's not actually stupid - because it's something that is a very strong predictor for zombie machines, and it's something that the "owners" of the zombies can't change, while legitimate operators frequently can.

    As someone else above mentioned, a service like FastMail (disclaimer: I work for FastMail) will provide you with a SMTP relay you can use for outbound email. You can still do your own SPF records, but you'll need to use the smarthost's outbound servers rather than your own IP.

    Still, if you can get the reverse fixed up you're part way there - if your IP isn't in the 'dialup range' RBLs as well.

  6. How to report a Yahoo bug to Yahoo by grok42tampabay · · Score: 1, Informative

    How to report a Yahoo bug
    to Yahoo.

    http://docs.yahoo.com/info/support/contacts/bugs.h tml

  7. another hurdle by artifex2004 · · Score: 3, Informative

    Guys, he's got a TXT record for SPF. If he starts relaying through his ISP's mail servers, he's either got to give up SPF, or add the appropriate include: modifier. Neither is particularly thrilling.

    Chris, I'm assuming you want to send out only from mail.~, since you have no PTR in the SPF, right? Still might be useful to add "A" to the SPF, since mail.~ is a CNAME. Or maybe not. :)

    And if it helps any, you seem to be clear off all the RBLs I was able to check.