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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 i...
#2: Post edited
by
Michael
·
2025-05-14T14:16:30Z (about 4 hours ago)
Revise for readability
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 one 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. For inbox searchability (which has been seriously impacted by this policy), I recommend replying to your original message and leaving the quoted body intact when you send the followup attachment.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 (particularly easy) way to circumvent email filtering *will become a spammer practice.* You absolutely do not want to still be doing this when it's an indicator of spam.
- 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.[^reply]
- 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[^mimic] 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.
- [^mimic]: Particularly a pattern that is as easy to follow as this one
- [^reply]: Hopefully, the reply to a successfully received message with the linked message IDs will also signal to the filtering software that you're legitimate.
#1: Initial revision
by
Michael
·
2025-05-14T12:48:32Z (about 5 hours ago)
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 one 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. For inbox searchability (which has been seriously impacted by this policy), I recommend replying to your original message and leaving the quoted body intact when you send the followup attachment. 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 (particularly easy) way to circumvent email filtering *will become a spammer practice.* You absolutely do not want to still be doing this when it's an indicator of spam.