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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.
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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.
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I think they're fixing the wrong problem, but it is a reasonable workaround… for now.
The real problem is that mail systems do not seem to trust your SMTP. Fix the underlying trust and filtering issue and the company no longer needs to rely on goofy schemes like your CTO's.
While they work that out, your CTO is right that knowing about a missing message is better than not knowing at all. Ideally he or she should make it clear that this is a temporary measure while they fix the root cause. Inbox searchability might be seriously impacted by this policy. To mitigate this, I recommend replying to your original message when you send the followup attachment and leaving the quoted body intact.[1]
Some words of warning: If I were an email filter, I'd find an attachment-only email to be even more suspicious than one with relevant accompanying text. You may find that the attachments are even less successful than before, depending on many factors.
Furthermore, even if this does work, any behavior[2] to circumvent email filtering will become a spammer practice. You absolutely do not want to be doing this when it becomes an indicator of spam. It could crater the reputation of your whole domain.
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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.
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