[Hidden-tech] Gmail is rejecting my outgoing mail as SPAM

Robert Heller heller at deepsoft.com
Fri Jun 17 15:15:15 EDT 2011


At Fri, 17 Jun 2011 12:21:46 -0400 Christine Polaczak <chris at cpdesignworks.com> wrote:

> 
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> 
> Dear Hidden-Tech community,
> 
> I'm in the process of sending an email to a long list of recipients.  
> I'm sending them individually, with a personalized salutation. The  
> subject line and the content is the same for each. There's also a  
> photo attached and imbedded within the text of the message.
> 
> Many of my messages are being rejected as undeliverable, with fatal  
> errors. They seem to be considered SPAM either by Google or the  
> recipients' providers.
> 
> How can I configure this mailing successfully?
> 
> Thanks in advance for your advice.

Some of the things considered spam:

1) Pure HTML E-Mail.  That is, HTML mail *without* a text/plain
alternitive part, in a multipart/alternitive message.  *Often* Spammers
use pure HTML E-Mail as a way to 'hide' phishing messages (pretending to
be a bank or Paypal and asking the user to enter their login or banking
creditials, for the purposes of identity theft (or plain old theft). 
Many spam filters mark this as spam and either drop it or reject it.

2) Many spammers ALSO 'personalize' their messages (often with errors
or with stupid salutations: 'Dear Info,' or 'Dear Sales,').  Since your
*content* is the same, it is highly probably that spam filters are
'learning' your content in the same way as they learned of all of the
insanely wealthy people who died without heirs in Nigeria...  A
personalized salutation is not going to enough to get you past spam
filters.

Is your 'long list of recipients' an opt-in mailing list?  Or something
else? It might make sense to use something like Mailman to manage this
list (including opting in or out).  Mailman (and other E-Mail list
software) includes certain mailing list header lines, which tend add
'negative' values to the spam score.  This offsets the spam score added
by some of the spam-like features of your E-Mail.  Yes, this means you
message *won't* be as personalized, but it might be the way you need to
go.

Also, but sending the messages one-by-one, your outbound mailer has the
appearence of sending a lot of mail and a lot of it 'looks like' spam
(the messages all look the *same*, with only minor differences) -- this
would tend to cause your outbound relay look like a spam source and this
also adds to the spam score and/or might get you blacklisted with
SpamCop, which will also cause E-Mail from your outbound relay to be
rejected.

> 
> Chris
> 
> Christine Polaczak
> chris at cpdesignworks.com
> 413 539-3582
> 
> 
> 
> 
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-- 
Robert Heller             -- 978-544-6933 / heller at deepsoft.com
Deepwoods Software        -- http://www.deepsoft.com/
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