Is it logical to require sending attachments in a separate follow-up email, to increase the chance that recipient receives at least one email? [closed]

my new company has this IT policy for emailing attachments. does it make sense? what do you think? First, employees shall email the recipient to inform them that you will be sending attachments in a separate, subsequent email. Don’t attach anything to this initial email. Then, in the second email, attach the file(s). the chief technology officer (CTO) claims that his policy of sending attachments in a follow-up email, is safer than sending just one email with attachments. because if the recipient's email flags the second email WITH attachments as spam, they shall still receive your first email without attachments, and know that they're missing the follow-up email WITH attachments. without this IT policy, if recipient's email flags the lone email as spam, then recipient shall miss your email.

Mar 27, 2025 - 12:36

my new company has this IT policy for emailing attachments. does it make sense? what do you think?

First, employees shall email the recipient to inform them that you will be sending attachments in a separate, subsequent email. Don’t attach anything to this initial email.
Then, in the second email, attach the file(s).

the chief technology officer (CTO) claims that his policy of sending attachments in a follow-up email, is safer than sending just one email with attachments. because if the recipient's email flags the second email WITH attachments as spam, they shall still receive your first email without attachments, and know that they're missing the follow-up email WITH attachments.

without this IT policy, if recipient's email flags the lone email as spam, then recipient shall miss your email.