Bulk legitimate email: Can I predict liklihood that the outgoing messages will be wrongly flagged as spam? -

the recipients represent wide variety of academic institutions , business organizations. many use free email accounts too, gmail , hotmail. there several thousand addresses in distribution list.

seems people on distribution list received recent sent email , had flagged spam. know there guidelines made available, these @ gmail, navigating spam filters. know not uncommon problem.

i not looking iron clad guarantee here, optimize result in terms of maximizing % email messages received. how emailers test prior sending?

is there sort of destination 1 can send email process message array of filters , provide report on percentage flagged spam , percentage delivered?

i understand tool aid evil spammer, i'd assume benevolence purposes of question. while asking recipients add "from" address address books some, i'd remove discussion well.

what's best way test legitimate email message "deliverability?"

thanks in advance comments -

perry
note: if misguided spammer, please away.

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some overlap question 2008:
how make sure email send programmatically not automatically marked spam?

and more recent one:
how make sure email send not automatically marked spam?

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spamassasin best answer. it'll give reasons why email may rejected can fine-tune it.