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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?"

6 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:Your ISP's ip-range is listed by kayen_telva · · Score: 3, Insightful

    did your post help at all ? just because you cant think of a reason to run your own server doesnt mean "There is really no good reason to run a mail server on your own machine". Why do people like you even bother replying. your post was pointless.

    a smarthost really is the most practical solution to this for now, until the climate of the internet changes (never?)

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

    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.

    Exactly, great response. I was thinking of taking my systems which are currently hosted at a colo several miles away and putting them in my office here, which is hosted off of cable (was thinking of moving to DSL possibly) and now I know that if I do move my systems, I may begin to encounter problems sending to free mail systems, and I'll know how to handle the situation if it does happen.

    Ask Slashdot often brings up interesting questions that are not always terribly important, but interesting nonetheless, and helpful sometimes to several people who may be dealing with the same issue at the same time, or may be in the future.

  5. I've had success with... by j-turkey · · Score: 2, Insightful

    Some time ago, I found that my company's mail was rejected by a large provider. Similar to your issue, our mails were also being rejected without any notice. I had good luck with calling the ISP. Once I got the right person on the line, we were able to diagnose the problem with ease. In my case, it was an incorrect reverse DNS lookup record that I had overlooked, which it was easily resolved. Your domain appears to have the same problem.

    You may want to see if your ISP will update your reverse lookup record to match your DNS info (unlikely if your DSL is residential). If they won't do this for you, consider upgrading to a business class service that allows you to run a mail server and gives you some control over your DNS record(s). If this turns out not to be the issue, your best bet is to contact the recipient's service provider(s). Once you get the right person on the line, you may be pleasantly surprised.

    --

    -Turkey

  6. 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.