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Q&A reasonable to mandate sending attachments in a separate follow-up email to ensure that the recipient receives at least one message?

In addition to what Michael said (+1), this would be quite annoying to recipients. It would be a hiccup in my workflow, and I'd think less of the sender. Their inability to fix their email system...

posted 3h ago by Olin Lathrop‭

Answer
#1: Initial revision by user avatar Olin Lathrop‭ · 2025-05-14T13:40:31Z (about 3 hours ago)
In addition to what Michael said (+1), this would be quite annoying to recipients.  It would be a hiccup in my workflow, and I'd think less of the sender.  Their inability to fix their email system shouldn't be my problem.

If you're sending legitimate email with legitimate attachments, they really shouldn't get rejected as spam as long as the number of attachments is reasonable and the overall size not excessive.  I know systems that refuse mail when the attachments add up to more than 10 Mb.  When you need to send someone large files, it is better to put them in an unlinked corner of your web site, a drop box, or something similar, then send only a link.  Unfortunately, some spam filters seem to trigger on such links too.