Why do my outgoing emails often get spam-filtered?

July 12, 2007 10:26 AM

More than half my outgoing emails wind up in spam folders. I realize that it's inevitable this will happen sometimes, but how can I minimize it? I use gmail, and I do not, fwiw, use words like "mortgage", "refinance" or "penis" in my messages. I sometimes use a sig, but it's non-hypeish. I do often send links in the body of my emails. One solution is to follow up re: unreplied-to emails, but 1. if someone did receive my mail but hasn't had time to reply, I look pushy and 2. chances are that my follow-up will be spam filtered, too.
posted by jimmyjimjim to computers & internet (16 comments total)

If you are sending the emails to people you regularly correspond with, make sure they add your address to their contact lists. Also, there should be a way for them to tell the spam catcher to exclude you. I'm not sure that anything you do in the e-mail itself will matter much, but greater minds than I will surely weigh in.

(Greater minds = anyone else.)
posted by The Deej at 10:38 AM on July 12, 2007

I correspond with a wide and ever-widening range of people. If it was always the same 20 people, that'd be a lot easier.

Also, my emails requesting that they white list my address would likely be spam filtered. :(
posted by jimmyjimjim at 10:41 AM on July 12, 2007

How is your email going out? Is your host/ISP spam-tolerant? Check to see if your mailserver is on any block lists.
posted by mrbugsentry at 10:45 AM on July 12, 2007

Well, using Gmail alone might get you some spam points. If you're not sending from Gmail's web interface you might get some points for not connecting from the advertised From domain.

Ensure that HTML mail is turned off (use "Plain text" not "Rich formatting").

Try to get a copy of one of the messages that ended up in a spam folder. If the receiving mail server is using SpamAssassin, it will include reasons the message was tagged as spam in its headers.
posted by grouse at 10:48 AM on July 12, 2007

From the SpamAssassin wiki - Tips To Avoid False Positives. If you like, send me an email (e.g. an anonymized version of something you've had a problem with) and I'll see what it gets marked down for.
posted by teleskiving at 10:48 AM on July 12, 2007

I use gmail, and have not experienced any such complaints about spam-foldering of mail I send.

How are you determining the 50% failure rate?

Also, it sounds like you are sending mail out to a bunch of people at the same time,
If it was always the same 20 people.

If you are listing everyone on the To: line together, many servers will assume your emails are spam. Using BCC will help those failures, since it makes the receiving server think it's just mailed to one person.
posted by nomisxid at 10:53 AM on July 12, 2007

Grouse, ah, that's great. Yes, I'm using Earthlink to send gmail via a POP client. That must be it.

I really want to stay with my POP client (Eudora), though, and I also like the flexibility of Gmail.

OTOH, I'd never use [e-mail]; being ISP agnostic, I need transportability.

teleskiving, thanks for the offer. will do so later.
posted by jimmyjimjim at 10:54 AM on July 12, 2007

It turns out that a lot of HTML formatting tags have an extremely high spam score on most filtration systems.

Plaintext emails nearly always rate much less spammy than HTML-encoded emails. So follow Grouse's advice, and turn off formatting.
posted by Steven C. Den Beste at 10:55 AM on July 12, 2007

nomisxid, "50%" is a very rough and thoroughly unscientific estimate. And no, I'm not doing mass mailings.

Formatting is (and always has been) off.
posted by jimmyjimjim at 10:56 AM on July 12, 2007

My gmail to my fiance's company usually gets blocked because they have their spam filter on "super duper annilihate mode."

Either that or fiance is just ignoring my request to pick up milk on his way home.
posted by desjardins at 11:17 AM on July 12, 2007

I have friend's whose work e-mail service routinely mark as spam or bounce messages sent from my GMail account using the Web UI. I think some companies set their thresholds for such things much higher. If you still want to use GMail interface you might consider getting your own domain name and use Google Apps for Domains which might cut back on the number of people who hold the gmail.com domain against you when calculating spam likeliness scores.
posted by mmascolino at 11:21 AM on July 12, 2007

jimmyjimjim, how do you know you're being filtered? i've never had this problem with my gmail account, either and a lot of what you're saying doesn't seem like it would register on filters to my mind.
posted by shmegegge at 11:27 AM on July 12, 2007

Yes, I'm using Earthlink to send gmail via a POP client.

My guess is this might not be right. You are probably receiving email via POP3 and gmail, but maybe sending them via a different server. Spam filters love to flag emails that say they are 'from' one server, but were actually sent from somewhere else.

In your Eudora settings, what's your outgoing/sending SMTP server?
posted by ghostmanonsecond at 11:52 AM on July 12, 2007

When you're sending via Earthlink, are you using Earthlink's SMTP server for outgoing mail or are you using Gmail's SMTP?

If you send out email that's "from" a Gmail address, but you send it via somebody else's SMTP server, it will get spam-points added to it by most filtering systems. (Because it'll look at the from address, and the IP of the server it came from, and see that they don't match. And thus conclude that it's got forged headers.)

Make sure you're using Google's SMTP server for all outgoing mail.

Here are instructions from Lifehacker.
posted by Kadin2048 at 12:01 PM on July 12, 2007

Yeah, eudora is indeed sending via smtp.gmail.com

hmph....
posted by jimmyjimjim at 12:20 PM on July 12, 2007

Check for multiple SMTPs in your email app. Are you sure that's the only smtp you are using?

Do you have a goofy signature?

Does your real name/username have a naughty substring like johhny cocksmith?

Do you have any embeded image or background in your html email?

Can you send plain text?

Do you usually send mail out without a subject line?

Check your encoding settings. Make sure your email is in a regular english encoding (not sure what its really called off the top of my head).

Perhaps try a different client for a while and see if it makes any difference.
posted by damn dirty ape at 12:57 PM on July 12, 2007