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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?

Aside from what others have said, the critical assumption behind this policy is that the recipient's email system will only flag emails with attachments as spam, and is guaranteed to let through an...

posted 8h ago by InfiniteDissent‭

Answer
#1: Initial revision by user avatar InfiniteDissent‭ · 2025-05-14T15:32:25Z (about 8 hours ago)
Aside from what others have said, the critical assumption behind this policy is that the recipient's email system will **only** flag emails with attachments as spam, and is guaranteed to let through any email which does not have attachments.

I see no particular reason to make this assumption. If email systems are treating your domain as an originator of spam, they might well be filtering all messages, regardless of attachments. While the presence of attachments is no doubt a factor in the various heuristics that are used to determine the probability of spam, it is not the only such factor.

So not only is it an inconvenience, but it may not even be solving the problem it's claimed to solve. If your CTO is claiming that sending an attachment-free initial message will "ensure" that the recipient receives at least one message, employees may be given a false sense of security which is worse than not having the policy at all.