Best way to send lots of email

[Sarah Reichelt]

On 9/7/05, J. Landman Gay <jacque at hyperactivesw.com> wrote:
> I told a friend I would try to help him set up a little database that
> sends email to a list of opt-in customers. To begin with there will only
> be a few names, but he is hoping that business will grow and there will
> be a few thousand eventually. I thought I'd just set up a simple stack
> that uses the excellent libSMTP to send the emails.
> 
> To protect each customer's privacy, we'd prefer that emails are sent out
> individually, or else in some way that doesn't display the other email
> addresses. That means we can't use CC lists. We could use BCC instead
> but then the recipient's name wouldn't be in the "To" field and some
> spam filters might block it.
> 
> If we send each email individually it could conceivably take a long time
> when the list gets larger, and spewing a lot of email at once could
> trigger an ISP's spammer alert. Does anyone know how many emails it
> takes before you look like a spammer?
> 
> What's the best way to handle a private mailing like this?

I agree that the best way to avoid spam filters is to use individual
emails which can include a personalised greeting as well as showing
the recipient in the "To" field. Make sure the "From" includes a real
name as well as the email address e.g.
  From: John Smith <john.smith at isp.com>
rather than
From: john.smith at isp.com

When testing, have the program send an email to you and to some
testers and get them to check the raw source and see what spam status
has been allocated to the email and why. That way you can re-structure
the email to minimize the likelihood of it being thought spam.

As regards trying to avoid looking like a spammer, I don't know how
this is triggered, but from what I have read, these spammers can send
out 30,000 emails an hour or something ridiculous. I reckon that if
you split it up so that you sent a bunch, waited a few minutes and
sent another bunch, it would be more reliable and less likely to be
misinterpreted. Also, if the email content doesn't trigger any spam
filters, that has got to look better.

HTH,
Sarah