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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?

My new company has this IT policy for emailing attachments. Does it make sense? The Chief Technology Officer (CTO) claims that sending attachments in a follow-up email is safer than sending a sing...

3 answers  ·  posted 20h ago by 7095‭  ·  last activity 2h ago by InfiniteDissent‭

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#1: Initial revision by user avatar 7095‭ · 2025-05-13T22:21:46Z (about 20 hours ago)
reasonable to mandate sending attachments in a separate follow-up email to ensure that the recipient receives at least one message? 
My new company has this IT policy for emailing attachments. Does it make sense?


The Chief Technology Officer (CTO) claims that sending attachments in a follow-up email is safer than sending a single email with attachments. The reasoning is that if the recipient's email system flags the second email with attachments as spam, they will still receive the first email without attachments and be aware that the follow-up email with attachments is missing. Without this policy, if the single email is flagged as spam, the recipient may miss the entire message.