My emails are being flagged as spam

February 26, 2005 11:58 AM

Emails I send are being flagged as spam.

Over the last 5 years or so I've run multiple opt-in mailing lists for my own site and the sites of others. In the past 6 months or so I've noticed a huge drop in the number of replies I get. Today, I test-sent some letters from each of my domains to my own Hotmail account. When I went and checked, all had been flagged as spam.

As I say, my mailing lists are all true opt-in lists. However, one of the lists only sends a couple emails a year (for the past 2 years). I'm assuming that some of the subscribers didn't realize what they were and flagged them as spam and this "spam data" has propagated to various email-hosting places.

However, I also sent some test-emails today from addresses that *are not* used for mailing lists and those also were sent to spam so I'm assuming these filters are working off my IP or something like that.

My questions are:

1. In general, what can I do about this?

2. I am in the process of starting a new project that has a fresh domain and has never sent an email. I was going to test it by sending to my hotmail account and seeing what happens. However, if I do this, will hotmail flag the new domain as a spammer since it's coming from the same IP?

3. Should I call my ISP (Rogers High Speed Cable) and request a new IP? How can I do this without getting their hackles up and thinking I'm a spammer?

4. What about non-hotmail services? Are these companies all getting their "spammer IDs" from the same pool? Is there some service that can be used to send a test message to to see if it's being flagged as spam? Are there Mefi members who use third-party spam-filtering services that would allow me to send them a test-message to see if it's coming through?

Sorry for the lengthy post but the majority of my online projects have been email-based and this is obviously quite distressing. Thanks!

posted by dobbs to computers & internet (20 comments total)

If you're running your own mail server (or using mail-sending software that delivers directly to the destination mail server) on a basic cable modem connection, then your mail is quite likely to be viewed as spammy by a lot of systems. Changing to sending out mail through your ISP's SMTP server may help (of course, your ISP's server may not be competently run). Also, if you are sending directly from your own machine, then you need to have a nongeneric reverse lookup (PTR record) for the IP address, not some long combination of IP-address-derived numbers and geographic abbreviations that looks like you're someone's home computer.

Getting mail to people on big ISPs (or even small ISPs) is a challenge nowadays. Spam is pretty much killing e-mail marketing. AOL provides some useful information at http://postmaster.info.aol.com. I haven't really seen anything similar for other ISPs.
posted by Axaxaxas Mlö at 12:10 PM on February 26, 2005

there's a site you can go to that shows if your mail server is on a whole pile of blacklists. you can track it down on google.

after asking here i started routing my email through dyndns.org. that thread has other solutions, some free. i chose dyndns because i also used them for dns routing and wanted to pay them something in return. works like a dream, but they charge by number of emails (in bands). i have so few subscribers that it doesn't matter. :o)
posted by andrew cooke at 12:17 PM on February 26, 2005

hmmm. i can't find the combined database, but here are links to individual lists.
posted by andrew cooke at 12:22 PM on February 26, 2005

ah, here's one. enter your mail server address in that little box and wait.
posted by andrew cooke at 12:24 PM on February 26, 2005

Thanks for the answers so far. Here's some more information (and sorry if it sounds way layman, I have no idea about how email works beyond sending and receiving):

1. I used to run one of the lists from my computer, when the subscriber-base count was manageable. When it got to the thousands, I switched it to my web-host's mailing list option (Dreamhost's Announce List feature).

2. For my non-list mail (which comes from the same domain as the list mail but not the same email address), I just use basic email thingies like Entourage or Thunderbird and the smtp server that Dreamhost assigns each domain.
posted by dobbs at 12:26 PM on February 26, 2005

sorry, i didn't explain those lists. a lot of filtering is based on the address of the machine that "sends" the email. that's the first machine that launches the email out onto the internet via SMTP (which is a protocol like HTTP, but for mail not web pages).

if you were running, say, sendmail on your own machine then that machine probably (depending on how it was configured) would be the address checked.

if you are using webmail, ot an email program configured to use your ISP's mail server, then the address used would be that if your ISP's mail server. it would *not* be the machine you were using when you sent mail.

the simplest way to find out what the address is is to look at an email sent to the relevant list (get a copy from a subscriber or subscribe yourself). look at the headers. you'll see things like:

Received: from aaa.bbbb.cccc.dddd (pp.qq.rrr [Z.Y.X.W])
     by xxx.yyy.zzz (8.12.8/8.12.8) with ESMTP id j1MFh0Dt000678
     for ; Tue, 22 Feb 2005 12:43:00 -0300

the address you want is the first "received from" (ie the bottom one in the list of headers). enter it in the page i gave above and see if it is on any blacklists. if so, and they are important lists, then you need to get unblocked or change the machine you send email from. one solution is to use the services i asked about.

that's just one way to filter spam. people may also filter by content. given what some of your mailing lists are/were about, that might be relevant too.

sorry if i'm still not answering the question. it's difficult to tell you what to do to cure the problem until you've tracked down what's causing the problem.
posted by andrew cooke at 12:42 PM on February 26, 2005

Other ISPs may be different, but the medium-large ISP I work for will make a reverse pointer for static IP addresses (that is, 66.123.66.123 points to mail.yourdomain.com rather than ppoe-123-456-lagh-tralalalala.isp.com. In some cases, that reverse pointer may be all you need, because many mail systems simply flag as spam any mail where the from domain doesn't match the reverse lookup. So if you're sending from [e-mail], but your mail comes from 66.123.66.123, which resolves to ppoe-123-456-lagh-tralalalala.isp.com instead of dobbsstuff.org, they're going to see that as a problem.

You can also see if your specific IP range has been blocked by going here (lots of other fun tools there, too): dnsstuff.com. If it has, you can work with your ISP to get those blocks removed (in most cases a good ISP is aware of which ranges are blocked and work constantly to resolve those issues.)

I would suggest sending an email to [e-mail] as a first step (or do a whois lookup--you can do this at dnsstuff, too, if you like; just use the abuse lookup tool) and see if they have an abuse address listed. If you get an automated reply, don't despair, because it will likely have further instructions regarding how to contact a real person, and you can go from there.

Good luck. :>
posted by littlegreenlights at 12:51 PM on February 26, 2005

Send mail to an account that has some sort of spam filtering tool that shows why it is filtered as spam - my email has SpamAssassin on it and you get a report like this:

Content analysis details: (5.20 points, 5 required)
X_AUTH_WARNING (-0.4 points) Has a X-Authentication-Warning header
MAILTO_TO_SPAM_ADDR (0.4 points) URI: Includes a link to a likely spammer email address
RCVD_IN_ORBS (0.5 points) RBL: Received via a relay in orbs.dorkslayers.com
[RBL check: found 4.16.98.199.orbs.dorkslayers.com.]
RCVD_IN_OSIRUSOFT_COM (0.6 points) RBL: Received via a relay in relays.osirusoft.com
[RBL check: found 4.16.98.199.relays.osirusoft.com.]
FORGED_MUA_OUTLOOK (3.5 points) Forged mail pretending to be from MS Outlook
MISSING_OUTLOOK_NAME (0.6 points) Message looks like Outlook, but isn't

That's not actually from a spam mail, but from a guy I know who has his mail set up pretty weird. Hopefully a similar report on your mails could tell you what is setting off some filters.
posted by TheOnlyCoolTim at 1:03 PM on February 26, 2005

I've found that the basic issue that littlegreenlights points up has become a huge factor over the past year or so in whether or not mail gets flagged--basically, if the IP/domain info for the "From" address doesn't match the info for the originating STMP server ("From: [e-mail]", "smtp.mydomain.com"), then the likelihood of getting flagged goes _way_ up.
posted by LairBob at 1:58 PM on February 26, 2005

Send a mail to me (email is in profile) via your list interface with a subject "AskMe" and I'll tell you what SpamAssassin thinks is wrong with it, like what TheOnlyCoolTim gives an example of above.
posted by zsazsa at 2:38 PM on February 26, 2005

Still going through most of the posts and checking stuff.

zsazsa, I sent you an email from my regular account (I can't send thru the list without mailing everyone). Thanks!
posted by dobbs at 2:57 PM on February 26, 2005

Well, SpamAssassin didn't think there was anything wrong with it:
X-Spam-Status: No, score=-2.6 required=5.0 tests=BAYES_00 autolearn=ham version=3.0.2

There must be something strange with emails sent through the Announce List interface. I checked the headers and the test mail went through dreamhost's servers, after originating from dobbs' cable modem.
posted by zsazsa at 3:54 PM on February 26, 2005

zsazsa, thanks for that. The thing is that the emails I've sent to my own hotmail account are from the same account that the email I sent you is from--not from my lists.

Weird.

When I punch my IP into those checker sites I come up as being on 3 of the lists. I'm gonna try to get them to delist.
posted by dobbs at 4:11 PM on February 26, 2005

Mail servers usually don't check the first originating IP against the blacklists, as they're usually on dialup, dsl, or cable. Any subsequent servers will be checked, especially the last hop before it reaches the recipient's mail server. There are dynamic/dialup blacklists that are supposed to prevent such people from sending mail directly, bypassing legitimate mail servers. Your IP is probably in those ranges, which really isn't a problem. You'll actually want to check the server that Dreamhost's Announce List email goes through.
posted by zsazsa at 4:23 PM on February 26, 2005

Hmm. Okay.

A few more stupid questions: I own multiple domains but they're all at Dreamhost and set up in the same way I emailed you. Do all these spam checker things just check numbers and whatnot or do they look at domains as well? One of my domains has the word shag in it and the other has the word trash in it. I always fear those are bad things.

I'm suspicious because often I email people for the first time and I never hear back. This happens like... I dunno at least half the time and maybe 7 out of 10 times. I find that strange. (I mean, sure, maybe they don't like me or are just ignoring me but I like to think that's not the case.)
posted by dobbs at 4:37 PM on February 26, 2005

1. In general, what can I do about this?

Change your email name to something besides EnlargeYourPenis. :-)
posted by curtm at 4:48 PM on February 26, 2005

It could also be flagged as spam because the program which sends the emails out has a signifier which marks it as coming from a non mail-client source. I use a delphi DLL to send emails, and the line "X-Library: Indy 8.0.22" in the header isn't liked by spam filters.
posted by seanyboy at 5:12 PM on February 26, 2005

Mail servers usually don't check the first originating IP against the blacklists,

ack. sorry i got that wrong. as zsazsa says, they check the last one. if you're running the smtp server yourself, that's you. otherwise it's your isp (unless there's multiple hops, but normally the check is at any gateway that precedes internal redirects).
posted by andrew cooke at 9:03 AM on February 27, 2005

These two content checkers won't help solve your current problem but may be useful going forward:
Lyris e-mail validator and SpamCheck. Good luck, keep us posted.
posted by madamjujujive at 10:28 AM on February 27, 2005

Bah. Thanks for all your help but I think my head is about to explode. This stuff's too complicated for me.

It really angers me how Spammers fuck everything up for everyone--not to mention the morons who buy shit from them. Ugh.

Though my new project was going to incorporate a new mailing list I think I'll just nix the plan and go RSS--not nearly as nice for the kind of shit I do but solves the problems pretty easily and forces me to learn a new tech thingy, which I suppose is good.

One other thing, though: it's kinda fucked that hotmail is sending my regular, non-list emails to spam folders. If I send an email to a bunch of friends with hotmail accounts and get them to click "this is not spam" will that help the hotmail spam identifier globally or just for their own accounts?

Thanks, all!
posted by dobbs at 1:40 PM on February 27, 2005