[tlug] Making sure people get the message

[Dave M G <martin@example.com>]

TLUG,

Apologies if this veers off topic, as it is more about email handling 
than Linux management.

I am involved in a few different groups which I communicate with via 
various email methods, such as mailing lists, and mass BCC mailings.

What I've noticed more and more in recent years, is that because of ever 
increasing anti-spam measures, there are often cases where people don't 
receive the email I send out. That an email comes from a majordomo 
mailing list, or is BCC'd to them seems to be a significant factor for a 
lot of email security systems.

Hotmail is particularly bad when it comes to this, and I wish I could 
just tell everyone who uses Hotmail to not. But I can't really do that, 
and in any case, Hotmail is certainly not the only offender.

In cases where I'm communicating regularly with a group, this problem is 
overcome eventually because if someone is not getting my messages, 
they'll say "hey, I never heard from you about X". In that case I can 
respond directly and say "well, make sure your spam settings aren't 
blocking me". They'll then discover that my email is in their junk mail 
folder. Thereafter it's not an issue.

However, I am wrapping up a project that requires I send out one last 
email, with some very important closing information. I have a duty here 
to try my best to ensure that everyone gets this email, and I want to 
make every effort to ensure that everyone gets it.

Because this last email going out is going to a group that I reach very 
infrequently, and that I'm mailing from an email address most of them 
don't already have, I'm worried that if I BCC it or use majordomo, up to 
30% may not get it. And they aren't necessarily expecting this 
particular message, so I can't rely on anyone contacting me to alert me 
that they haven't got it. Nonetheless, it is certain that they would 
want to receive the information I have for them, as it informs people of 
the results of the project that everyone worked very hard on.

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.

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. But it turns out that for some reason 
those emails also get marked as spam. About a third of new members who 
sign up initially complain that they don't get the message.

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?

We're talking a list of about 100 people. I could do it one by one over 
time with some copying and pasting. But... well, weren't computers 
invented to remove the repetition of tasks like this?

Any advice or information would be much appreciated.

Thanks.

--
Dave M G
Ubuntu 6.06 LTS
Kernel 2.6.17.7
Pentium D Dual Core Processor
PHP 5, MySQL 5, Apache 2