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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?"

5 of 86 comments (clear)

  1. Re:I've run 2 ISP's, starting my third... by bartle · · Score: 4, Insightful
    I don't understand why everyone assumes that anyone who Asks Slashdot is an idiot. I have a static IP and as I said, I'm not on any RBLs that I can find.

    My email address is listed in the post. I would think that anyone who would bother to reply might also be bothered to do a little probing of their own to see if their reply has merit.

  2. 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.

  3. Re:I've run 2 ISP's, starting my third... by jpkunst · · Score: 5, Insightful

    Google really *would* have answered this.

    Certainly. But the point of Ask Slashdot is that now others can read the answers too and learn something new, even if they were not searching for an answer to that particular problem at the time.

    These "Just Google it" replies really miss the point, IMHO.

    JP

  4. 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.
  5. Duh, yourself. by fmaxwell · · Score: 4, Insightful

    Rather than connecting directly to Yahoo's or Hotmail gateways, use your ISP's mail relay. That's what it's there for.

    Problems:

    1. Many ISPs won't relay mail unless the "From:" is in the ISP's domain. This prevents forgeries by zombies that try to relay through with random from addresses. More importantly for the ISP, they get to use viruses and spam as an excuse to force you to use their e-mail address, making it harder for you to switch ISPs.
        1a. Yes, I know about "Reply-To:." Many brain-dead mail servers, list servers,
                  and even e-mail clients apparently don't.

    2. ISPs often have limitations on attachment size. If I want to e-mail a 9MB file to a client or family member that can't deal with passworded FTP, I don't need my ISP's mail server rejecting the e-mail.

    3. ISPs often disallow attachments which are executable. Again, not a hassle when dealing with computer-savvy recipients, but not all recipients are that sharp.

    4. If the ISP ends up on a blacklist, your e-mail doesn't go through to mail servers that use that blacklist. I have a much better ability to control spam going through my server than to control spam going out through my ISP's mail server.

    5. You're at the mercy of the ISP. It their mail server goes down or experiences other problems, your outgoing e-mail is either lost or delayed.

    6. If there are e-mail delivery problems, your server won't have useful logs (since the actual delivery was attempted by your ISP's mail server. You won't be able to tell how many times a message was retried, whether something timed out in the protocol, etc.

    7. I'd rather not have my ISP retaining copies of my e-mail, auto-scanning it with who-knows-what software, passing it on to the FBI for warrantless PATRIOT Act fishing expeditions, etc. While I know that they could do that with a port 25 snoop, chances are that they wouldn't routinely do that.

    Yes, I know that there are inconvenient workarounds for some of the problems listed above, but, all in all, it's far preferable to use your own server.