I’m looking for a list of “rules” to follow when sending out bulk
email that will minimize the likelihood that the email will be
identified as spam by a filter.  We send out a monthly newsletter to a
large subscriber base and want to make sure our style is not causing
us to be filtered as spam.

I understand that there are key words to avoid in a subject header as
well as phrases and content styles can minimize this problem.

What are the specific words to avoid in a subject header?  What are
the specific things to avoid when designing the content of an email? 
Please provide any and all available information to help us with this
problem.  We also request that any information be backed up by URLs as
cited reference.

Hello cclegg06

Here is an article with some hints on how ezines can avoid being
trapped by spam filters, together with a selection of default triggers
found in Outlook http://www.ezineannouncer.com/ezines.html (“Beware Of
The Silent Ezine Killer!” by James Potash)

Another article with an overview of the problem:
http://www.itworld.com/nl/ebiz_ent/08052002/
(“Enterprise Email: Write for Two Audiences “ by James Lewin)

This article looks at how a spam filter analyses an email message and
gives some hints on how to avoid getting caught in a spam filter:
http://www.boldfish.com/BF_emguide/Notes/spam-filters.html
(“Spam Filters: The good, the bad, and the ugly”)

And more hints here:
http://www.workz.com/cgi-bin/gt/tpl_page.html,template=1&content=2633&nav1=1&
(“Avoiding the Spam Trap” by Alexandria K. Brown, 'The E-zine Queen' )

You can find all the default words and expressions used by Microsoft
in the filters.txt file which is available on the Microsoft site at
http://office.microsoft.com/Assistance/9798/newfilters.aspx  Note that
even something as innocuous as the phrase “Dear friend” is included as
a trigger.

Here are words and phrases used by the McAfee spam killer, together of
examples of how they might be used inadvertently and innocently in
personal and business emails:
http://www.startupinternetmarketing.com/ezines/filters.html (“Spam
Filters Run-Amuck
Is Your Message Getting Through?”  by Tim Gross) 

And a list of 250 words and phrases obtained from two spam filter
lists: http://www.wilsonweb.com/wmt8/spamfilter_phrases.htm (“Words
and Phrases that Trigger Some Spam Filters” by Dr. Ralph F. Wilson,
E-Commerce Consultant, Web Marketing Today, Issue 119, December 3,
2002)

Here is a more-detailed article that looks not just at content but at
some of the technical aspects of how to ensure that your messages are
not identified as spam, eg it looks at choice of ISP, configuring
email delivery infrastructure, monitoring your mailing base. It makes
the point that at least 12% of permissioned email is not delivered
because it is identified as spam by the receiving ISP.
http://www.assurancesys.com/f/avoid-spam-filter-trap.pdf (“An
Assurance Systems Brief: Avoid the Spam Filter Trap”)

Search strategy: spam filter words

I hope that this answer provides the information you are seeking.
Please use the request clarification feature if you have any questions
or problems.

Thank you