I'm on a blocklist! HELP!

Recently, an abuse desk rep asked what to do when customers were complaining about being assigned an IP address located on a blocklist. Because not every blocklist actually affects mail delivery it’s helpful to identify if the listing is causing a problem before diving in and trying to resolve the issue.

  1. Find out whether mail is actually being blocked, or whether the customer just went to one of the jumbo economy blacklist checker sites.
  2. If no mail is being blocked, it’s not an issue.
  3. If mail is being deferred (Yahoo…) it’s not the same issue as being blocked, and likely isn’t worth pursuing.
  4. If mail is being blocked, don’t take the customers word for why. If they got an email rejected by, say, Earthlink for some reason and then went to the blacklist checker and discovered that they’re listed on FIVETEN, they might grab onto that listing like a rabid terrier when it’s really an irrelevant rathole.
  5. Start with the rejection message. If it has a URL in it, that’s all you need to start with.
  6. If not, see if it’s consistent – does test mail get rejected. If not, it’s either a transient issue or it’s a content-based block rather than an IP based block, and hence not your problem.
  7. If there’s no URL in the rejection, contact the entity that blocked the mail, perhaps.
  8. Make a good judgement call about whether it’s worth caring. If it’s just one guy in his Mom’s basement blocking mail then it’s not worth the time or energy to care about the issue.
  9. If this is really business-critical for the customer then they should talk to a decent consultant rather than relying on their abuse desk for assistance.

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JD posed a question in my post about Postini and trying to sort out a customer getting marked as spam by their filtering mechanism and I think it bears more discussion than can be done in comments.

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Greylisting: that which Yahoo does not do

Over the last couple days multiple people have asserted to me that Yahoo is greylisting mail. The fact that Yahoo itself asserts it is not using greylisting as a technique to control mail seems to have no effect on the number of people who believe that Yahoo is greylisting.
Deeply held beliefs by many senders aside, Yahoo is not greylisting. Yahoo is using temporary failures (4xx) as a way to defer and control mail coming into their servers and their users.
I think much of the problem is that the definition of greylisting is not well understood by the people using the term. Greylisting generally refers to a process of refusing email with a 4xx response the first time delivery is attempted and accepting the email at the second delivery attempt. There are a number of ways to greylist, per message, per IP or per from address. The defining feature of greylisting is that the receiving MTA keeps track of the messages (IP or addresss) that it has rejected and allows the mail through the second time the mail is sent.
This technique for handling email is a direct response to some spamming software, particularly software that uses infected Windows machines to send email. The spam software will drop any email in response to a 4xx or 5xx response. Well designed software will retry any email receiving a 4xx response. By rejecting anything on the first attempt with a 4xx, the receiving ISPs can trivially block mail from spambots.
Where does this fit in with what Yahoo is doing? Yahoo is not keeping track of the mail it rejects and is not reliably allowing email through on the second attempt. There are a couple reasons why Yahoo is deferring mail.

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Why do ISPs do that?

One of the most common things I hear is “but why does the ISP do it that way?” The generic answer for that question is: because it works for them and meets their needs. Anyone designing a mail system has to implement some sort of spam filtering and will have to accept the potential for lost mail. Even the those recipients who runs no software filtering may lose mail. Their spamfilter is the delete key and sometimes they’ll delete a real mail.
Every mailserver admin, whether managing a MTA for a corporation, an ISP or themselves inevitably looks at the question of false positives and false negatives. Some are more sensitive to false negatives and would rather block real mail than have to wade through a mailbox full of spam. Others are more sensitive to false positives and would rather deal with unfiltered spam than risk losing mail.
At the ISPs, many of these decisions aren’t made by one person, but the decisions are driven by the business philosophy, requirements and technology. The different consumer ISPs have different philosophies and these show in their spamfiltering.
Gmail, for instance, has a lot of faith in their ability to sort, classify and rank text. This is, after all, what Google does. Therefore, they accept most of the email delivered to Gmail users and then sort after the fact. This fits their technology, their available resources and their business philosophy. They leave as much filtering at the enduser level as they can.
Yahoo, on the other hand, chooses to filter mail at the MTA. While their spamfoldering algorithms are good, they don’t want to waste CPU and filtering effort on mail that they think may be spam. So, they choose to block heavily at the edge, going so far as to rate limit senders that they don’t know about the mail. Endusers are protected from malicious mail and senders have the ability to retry mail until it is accepted.
The same types of entries could be written about Hotmail or AOL. They could even be written about the various spam filter vendors and blocklists. Every company has their own way of doing things and their way reflects their underlying business philosophy.

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