How to make sure a multiple-recipient is not marked as spam?
January 22, 2010 2:16 AM   Subscribe

I want to send an email to several hundred school principals and am wondering if it is likely to be spam-filtered, given the amount of recipients. The content of the email is a clarification of some points that appeared in an educational journal (it is not spam of any kind). Would putting the addresses in the BCC box make any difference (other than hiding all the other recipients)? I'm using gmail, but Eudora is an option (although I have never used it before).
posted by strangeguitars to Computers & Internet (23 answers total)
Technically, Bcc would definitely make a difference, since the recipient won't be able to distinguish a multi-recipient email from a single-targeted one (unless multiple recipients are on the same mail server).

As an Internet-old person, I wouldn't send an email to hundreds of people anyway. If it's about an article in a journal, send a letter to the editor if you want to reach the readership.
posted by themel at 3:01 AM on January 22, 2010

Have they asked for the clarification or otherwise done something to indicate that they even want this clarification? Because the way I read your question, you saw something incorrect in an educational journal and thought that these school principals would need to see a clarification.

Not saying that you're intend is in any way malicious or anything.
posted by theichibun at 3:08 AM on January 22, 2010

Response by poster: Let me clarify my question a little: it's a technical question, not a moral question. I'm not asking whether or not I should send the email, just if it will end up marked as spam if I do. Sorry for the confusion.
posted by strangeguitars at 3:25 AM on January 22, 2010

I'd definately BCC: but I think the receiver can still tell how many people have been BCCed and mark as spam. (especially if its 100)

You might want to send out say 10-20 addressees at a time.
posted by mary8nne at 3:30 AM on January 22, 2010

Yes, it will be marked as spam, because it is spam (unsolicited bulk email) whether you think it's important or not.

It's not just a question of the receiver either - your outgoing email provider may block your account if you start trying to email 300 people at once (or even just the same email to 10 people 30 times).

If it's that important, write to the journal and request a correction (way more effective than an email) or post letters to the principals (somewhat more effective than an email) instead.
posted by EndsOfInvention at 3:44 AM on January 22, 2010

Another etiquette reason you want to Bcc is that any unsolicited message to a group of that size w/o Bcc is pretty much guaranteed result in an orgy of escalating "Where did you get this address?" "Please remove me from your list!" pleas sent to everyone on the recipient list, annoying everyone more than the initial email.
posted by themel at 3:57 AM on January 22, 2010 [3 favorites]

Best answer: Google has information on bulk email. For example, if there are more than 500 recipients, or a large number of undeliverable emails, they will temporarily disable your account. More bulk sender guidelines.
posted by Houstonian at 4:10 AM on January 22, 2010 [2 favorites]

I agree with EndsOfInvention. It will be marked as spam as that is what it is.
posted by Nufkin at 4:31 AM on January 22, 2010

Response by poster: Houstonian, thank you!

Nufkin: I didn't say it was unsolicited. I regret saying anything about the content of the email as that is both complex and irrelevant. I clearly said that it was not spam of any kind.
posted by strangeguitars at 5:11 AM on January 22, 2010

If the emails aren't unsolicited, then you can always ask the recipients to sign up to a mailing list (e.g. a Yahoo Group), and then send them emails that way.
posted by EndsOfInvention at 5:23 AM on January 22, 2010 [1 favorite]

Best answer: If this is a legit email, why not use one of the bulk emailers like iContact or Bronto? They should be able to help you do this and they even have tools to track the response.
posted by wrnealis at 5:31 AM on January 22, 2010

wrnealis has a great idea. Those tracking tools can be quite valuable to genuinely log important information, like if there are any clickthroughs to links you may have in your email, and how quickly people delete it.
posted by carlh at 5:50 AM on January 22, 2010

I have a few email lists that I run, with anywhere from a few hundred to a couple of thousand people. The lists are handled manually, so , while the people all opt-in, I’m pretty sure there’s nothing from a technical perspective that would let a server know that what I’m sending isn’t spam.

What I’ve done at times is- send a few copies of the message, each bcc’ed to around a hundred recipients. In my experience, these messages are not marked as spam, at least not for most recipients. (One reason, I suspect, among many, is that regular spam messages go to way way more than a few hundred people).

One thing to keep in mind – your own ISP may have a maximum number of BCC’s on a message, or a maximum number of messages/recipients per hour. The number, and how the ISP handles it, will vary from provider to provider. If you send through gmail, you’re subject to the rules that Houstonian linked to. If you use Eudora, you’re subject to the rules of your ISP. You’ll have to find out what they are, and your ISP may or may be good about having a clear policy that the express publicly.
posted by ManInSuit at 6:17 AM on January 22, 2010

"may or may NOT be good about having a clear policy that THEY express publicly."
posted by ManInSuit at 6:24 AM on January 22, 2010

I'm not sure how Google treats BCC, but my mail server makes it send every message individually as a different spool.
[1] Client --> mail server. Send this message to server A. OK!
[2] Client --> mail server. Send this message to server A. OK!
Instead of Server A thinking it's the same message, it appears as 2 different messages because they're all being sent independently. Working in a school, we send a weekly newsletter to parents and Yahoo used to flag all our mail as spam until I got the secretaries to use the BCC field and magically, it worked.

Also consider that even if the receiving mail server figures out that it's all really the same message, you'll most likely be sending to different mail servers decreasing the likelyhood of spam tagging.
posted by jmd82 at 6:37 AM on January 22, 2010

I clearly said that it was not spam of any kind.

Just because you claim it is not spam does not mean it is not spam. You do not have to be selling something to make it spam.

If this is legitimate and desired, then set up a Yahoo or Google group to send the messages.
Trying to work around technical limitations by e-mailing a few people at a time may result in you losing access to your e-mail account or your Internet service altogether.
posted by grouse at 6:44 AM on January 22, 2010 [1 favorite]

(Can we try and respect the wishes of the OP, and not argue whether this isi the right thing to do, or whether the message is or isn't spam. There are plenty of situations in which a person might legitimately want to send an email to a few hundred people, who might legitimately want to receive it.)
posted by ManInSuit at 6:53 AM on January 22, 2010 [3 favorites]

Yes, and setting up a mailing list with a reputable provider (as I and others suggested) is the way to do that legitimately (and is easier than BCCing a small number of people at a time as well). If you want to talk about the behavior of other users instead of answering the question, you can send a MeMail or take it to MetaTalk.
posted by grouse at 7:20 AM on January 22, 2010

BCC is a header used on the client side only for specifying addresses that should not go in any headers for recipients to see. If you put it in BCC, it just gets used as a recipient address but not marked anywhere.

The addresses mail is sent to have nothing to do with the mail headers To, CC, and BCC - these are conventions used by clients to indicate to recipients only. The actual addresses sent to can be totally different than what is displayed in the to/cc fields.

When you receive a mail there is no way to see the BCC addresses unless the client made them explicit. Gmail does not. An email BCCed to 500 people looks the same as one BCCed to 5 or none.

Having too many emails on to/cc can set off spam filters both software and wetware (human). Most savy people see lots of recipients as either naive or malicious.

Using BCC sets off filters (software and wetware) because there is no indication the mail was addressed to the recipient. Some clients rectify this if all recipients are in BCC by sending individual mails to each recipient adding the recipient's email to the To header one by one. Some spam filters treat an email without the recipient's email address in the To/CC as suspect.

Your best bet is to send individual emails each slightly personalized to match the recipient's name and address. Even that can set the sending mail server to flag the emails as possible spam given the similarity among many emails being sent at around the same time.
posted by ydant at 7:23 AM on January 22, 2010 [1 favorite]

One more, netiquette reason for using the Bcc field is that many people object to their email addresses being made public. I know I do.

When I was tasked with sending out a daily press review to some 50-60 clients, I put my own address in the To field; this avoided the suspicious "Unspecified addressee" which some servers add to a blank To field, and helped suggest the open and bona fide nature of the mail. Then everybody else in the Bcc field - this worked well.

This is probably a good solution for a one-off occasion. The post doesn't read as though it is planned to be the start of a regular email service, so the OP may decide that setting up a mailing list with a provider, however useful that might be longterm, is too much hassle for a single mailshot.

And I think everybody upthread has been trying to respect the wishes of the OP by suggesting ways to make this work. Only one poster touched tangentially on the issue of whether it is the right thing to do. And those who insist it is spam do not appear to be suggesting "spam" in the sense of evil ripoff/sales/advertising material, but "spam" in the purely technical sense of unrequested bulk mail which will be recognised as such by a server and cause the mailshot to fail, nothing more.
posted by aqsakal at 7:39 AM on January 22, 2010 [1 favorite]

I'd recommend the mailing list solution as well, but if you decide not to go that route, another point in favor of BCC is that it protects you from idiots who don't understand the difference between "Reply" and "Reply All," or don't understand when to use one or the other. Since none of the other Bcc'd recipients appear on each recipient's email, an accidental (or malicious) "Reply All" comes back only to you, and you don't get a dozen people's "please remove me from your mailing list" sent to every single principal on your original list.
posted by DevilsAdvocate at 7:40 AM on January 22, 2010 [1 favorite]

I've done email marketing campaigns with hundreds of recipients (these folks were members of an association I worked for, and so were expecting contact).

The best way to avoid getting blocked by a spam filter is to use Microsoft Word's "Mail Merge" feature.

You can send individual emails to each recipient, and there will be less chance of the message getting junked. As an added bonus, you can personalize every single message if you want, which means it will have a greater chance of being read.

The only downside is that if you send out large batches of email (more than 50 at a time) you may be blacklisted by your ISP, so it's best to send it out in batches of 50 or so.

In my experience, mailing lists don't work for large groups, simply because more often than not people don't understand what they are and have to be educated, or it's just one more hurdle to participation.

Try mail merge. If you don't have a hosted email service, you can even set up using Gmail.
posted by KokuRyu at 7:56 AM on January 22, 2010

I just asked a friend who does this kind of thing regularly for an academic institution here in Rome. She uses emailbrain (check here). Says it's great and costs very little, but can't give details of cost because it depends on what options you use. Makes each email look totally individual.
posted by aqsakal at 8:48 AM on January 22, 2010 [1 favorite]

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