Caveats of doing a mass e-mail

April 29, 2006 2:08 PM

I want to send a large number of E-mails (like 500) to my customers. This isn't spam; they have definitely opted in and know me personally. I'd like to know if there is anything that might cause a problem here . . .

My main concern is (1) getting on a blacklist and (2) taking heat from the company that owns the SMTP server (Dreamhost hosted service). I intend to send them from my laptop through my ISP (Sprint DSL) to my Dreamhost shared hosting SMTP server (relayed but with my authorized login). So do I have anything to worry about?

My understandings are:
1. This is not too different from running a package like phpBB, which spouts out a lot of administrative E-mails daily, except that I'm connecting to the SMTP server remotely.
2. AOL/CompuServe will likely blacklist me, but I have no idea how this happens.

Again, this is not spam, and the customers have asked to be on my announcement list. Would it be safer to have some other company (or Dreamhost's "announcement" goodie) do it, or can I do it safely as long as I have opt-out info and maybe an X-header of some sort?

posted by chef_boyardee to Computers & Internet (9 answers total)

Response by poster: Also about the "500 E-mails"... I don't mean 500 E-mails per customer. Rather I mean one E-mail to 500 customers, maybe every few weeks or so.
posted by chef_boyardee at 2:09 PM on April 29, 2006

Dreamhost has a built-in Announce List feature exactly for this service. I run dozens of mailing lists for myself and clients without issue from them.

However, in my experience, you will be blacklisted no matter what, by certain companies. I've sent 10s of thousands of emails thru my own mailing list over the years and as a result, I often have difficulty with hotmail and/or aol users.
posted by dobbs at 2:11 PM on April 29, 2006

The problem is that -- depending on the ISP -- it only takes one user falsely reporting the e-mail as spam to get you on that ISP's blacklist. Be prepared to spend a reasonable amount of time getting yourself de-blacklisted from various places.
posted by littleme at 2:21 PM on April 29, 2006

Also, dreamhost has a limit of 100 mailings (each address counts as 1 mailing) per hour. So don't blast away. Use the mailing list.

Or, shoot, set up a Google group or Yahoo group and let them subscribe to that. You can set those up as one-way lists, and if AOL blacklists that, they're even more pathetic than I thought. I think Yahoo lets you pay a small fee to remove the ad-footers if you want.
posted by adamrice at 2:32 PM on April 29, 2006

Response by poster: I figured I'd give Google Groups a shot since it does support E-mail. However we'll see what becomes of this:

• Your request to add 241 new members has been flagged for review by our staff.

This may have happened for various reasons, including because it was a large request, or because you've recently made a large number of small requests.

You can help us evaluate your request and expedite its approval by telling us more about your request here. We appreciate any information you can provide to us, and will let you know our decision within 24 - 48 hours. Please note that we would not be able to process your request without your input.
posted by chef_boyardee at 3:09 PM on April 29, 2006

Also, dreamhost has a limit of 100 mailings (each address counts as 1 mailing) per hour. So don't blast away. Use the mailing list.

Huh? Where is this noted?

I have several thousand people on some lists and have never had any indication that they're only going out to 100 people per hour. In fact, Dreamhost's wiki specifically says no emails sent to the list should take longer than 6 hours to arrive. If they do, they recommend you contact support as something is wrong.
posted by dobbs at 4:58 PM on April 29, 2006

Oh, I think I misunderstood adamrice. I think he's talking about using DH without using the list.
posted by dobbs at 5:00 PM on April 29, 2006

You could outsource this function to another provider (bulk email providers). There are legitimate ones out there that exist solely to take the heat off you in the event of blacklisting etc.

Check out gravityMail. I've dealt with them in the past and it was very easy to setup and it's not very expensive (few hundred dollars for over 4000 email).
posted by purephase at 5:02 PM on April 29, 2006

You pretty much just have to take the risk and suck it up if something bad happens. People report the strangest shit as spam...

For example: I'm on AOL's complaint response system, so that if someone reports an email from my server as spam, I actually see what email it was.

A website I run has you enter your birthdate when you register for an account, and then on your birthdate it sends you a very short email that says something goofy like "Happy Birthday, since we have no budget or money all we can afford to give you is this junky email - hope it's a great birthday anyway!"...

Just the other day I had 2 of these reported as spam, despite the fact that they address the person by the username they signed up for at my site, clearly identify themselves as coming from this site, etc...

Bottom line is you probably won't get blacklisted, but there isn't much you can do other than pay attention and work with people to get yourself unblacklisted if it happens.
posted by twiggy at 11:22 PM on April 29, 2006