of course a copy appears in your sent folder, just as a copy would exist in a real filing cabinet if you took a photocopy before you placed it in an envelope and sent it snail mail. Also like snail mail electronic mail has absolutely no guarantees with regard to delivery. None. Whilst over the past 20 years or so email has been very reliable, that does not imply any guarantee.

I am aware of at least one email situation where any email with an attachment is automatically dropped and not delivered as the company views word documents as unnecessary for employees to do their jobs, but representing a real risk of email infection with malware.

I am also aware of people who set their email client to delete all mail that arrives from people not in their address book. They only want to hear from a chosen few.

I suggest you try sending your mail without the proprietary and risky word document and see if deliverability improves. My guess is at least some of the issues arise from that attachment being identified as risky by the recipients anti virus product of choice, or by their providers decisions about what it is appropriate to deliver.

Thanks Matt, but it happens to all recipients when it happens. I send the email to about 16 people and either they all get it or they all don't. And the only reason for the email is the newsletter attached, so it has to be there. The problem seems to me to be somewhere from me sending it to when the postmaster sends it (or not).

As I said before, drop the word document. So you have a newsletter, but nothing says you can not send it as HTML or PDF or even as HTML in the body of the email.