[tlug] Making sure people get the message

[<stephen@example.com>]

Dave M G writes:

 > It seems that what I need to do is ensure that my email isn't dismissed 
 > as a mass-email scam, is to have some way of ensuring that it has a 
 > proper "To:" and "From:" so that it looks like a direct, one to one, 
 > mailing. And at the same time, I want to respect people's privacy by not 
 > just throwing all the email into the "To:" field.

Actually, the most important precondition is that none of the
addresses be @example.com, @example.com, @example.com, @example.com, etc.  The problem is that
missing mail can always be blamed on the sender, while the ISP must
accept responsibility for letting spam through.

I don't recall the details, but for several years the AOL "mark this
message as spam" key was right next to another frequently used key.
So users were inadvertantly marking mail as spam.  Other users would
mark mailing list posts as spam to get "revenge" on some flamer, but
if more than two or three people did that, it would bump the
spamminess of the whole ML up, and it would end up on the blacklist.

That's the kind of "only one chromosome more evolved than a spammer"
ISP you're fighting against.[1]

 > In the case of one of my groups, I use a PHP script that reads all the 
 > emails from a database, and sends them out one by one. I would have 
 > thought that would do the trick.

Spammers have been on to that trick that since, well, since they
started spamming.

 > So, does anyone have any idea of any scripts, tricks, or anything so 
 > that I can feel reasonably sure that my email won't be stopped by overly 
 > enthusiastic anti-spam measures?

No.  If you send a mass-mailing, some of your recipients will lose mail,
unless they care enough to get accounts with better than average email
services.

However,

0. send the message to yourself and see what spamassassin says!

1. as Godwin recommends, if you have any out-of-Japan addresses,
   including Hotmail and friends, arrange to have the mail sent from
   the U.S. or Europe, and try to arrange that it's from a reputable
   domain.  (Eg, avoid wanadoo.)

2. if you can't do that, at the very least get it sent from an IP
   address owned by a large organization that is not a consumer ISP;
   mail from a dynamically assigned address pool is the kiss of death,
   and even if not, some spamfilters will nuke you if you're in the
   same net block with dynamically assigned addresses.  Sometimes
   sending via your ISP's MX will do, too.

3. do not send HTML mail, or multipart/alternative mail that contains
   an HTML part.  If your message needs to do multimedia tricks, send
   a reference to a web page with the multimedia.

4. do not include anything but text.

5. use a real mailing list manager such as Mailman which does proper
   bounce processing, and watch the bounce reports.  That will allow you
   to resend to the bouncees.  (However, you cannot depend on AOL at
   least to even send a bounce.)

6. set the MLM to use VERP, which (1) allows much more precise
   tracking of bounces, and (2) at least in the case of Mailman is
   required for full personalization.

7. fully personalize the message (ie, the only header addressee should
   be the person on the list).  Mailman's FAQs call this "an
   announce-only list".

8. a sending system set up for "SPF" (one arrangement for partial
   identification of sending systems) helps with some smaller ISPs.

Footnotes: 
[1]  Actually, most of the programmers try hard.  But the marketroids
drive these organizations, and spam is a hotbutton for all of them.  I
know at least two very competent ex-major-ISP mail admins who were
driven out by that kind of wrong-headed antispam policy.