There are a lot of outlook 2003 related bugs that have recently been fixed in CVS and are slated for 2.61..

http://bugzilla.spamassassin.org/show_bug.cgi?id=2344
http://bugzilla.spamassassin.org/show_bug.cgi?id=2538

Theoreticaly, these may fix your problem.

You can also look at the other Outlook/OE related bugs in 2.60:

http://bugzilla.spamassassin.org/buglist.cgi?short_desc_type=allwordssubstr&short_desc=Outlook&version=2.60&long_desc_type=allwordssubstr&long_desc=&bug_file_loc_type=allwordssubstr&bug_file_loc=&keywords_type=allwords&keywords=&bug_status=NEW&bug_status=ASSIGNED&bug_status=REOPENED&bug_status=RESOLVED&bug_status=VERIFIED&bug_status=CLOSED&emailtype1=substring&email1=&emailtype2=substring&email2=&bugidtype=include&bug_id=&changedin=&chfieldfrom=&chfieldto=Now&chfieldvalue=&cmdtype=doit&order=Bug+Number&field0-0-0=noop&type0-0-0=noop&value0-0-0=



At 12:20 PM 12/6/03 -0500, Charles Gregory wrote:
Greetings!

One of our users today reported a mis-identification of legitimate mail
primarily based upon two tests:
> >  1.1 FORGED_OUTLOOK_HTML    Outlook can't send HTML message only
> >  1.1 FORGED_OUTLOOK_TAGS    Outlook can't send HTML in this format



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