I've just started at a new organization and I'm facing a puzzling issue. We use Microsoft 365 internally, but we receive emails from various external contacts, including contractors who often use Gmail or other webmail services. These contacts are trying to reach a shared mailbox, like [email protected], but occasionally, about once or twice a month, an email intended for that mailbox mistakenly goes to an executive instead. The common thread is that the senders claim their email autofilled the executive's address when they were typing, despite the exec having no direct connection to them. I'm confused about how they're even getting the exec's email address in the first place since they don't have any prior communication with this person.
4 Answers
Have you checked if the executive’s email is in your organization's Global Address List? Sometimes it might appear there even if they’ve never been directly contacted.
It’s possible that the exec was CCed in some previous email, and since Gmail can sometimes suggest contacts based on prior interactions, they may be seeing their email in the suggestions. I’ve noticed that Google seems to pick up on some email threads but not all, which could explain the accidental autofill.
Considering the rise of AI, could Gmail's algorithm be suggesting addresses based on past correspondence? If they're saying it's "autofilling," that might be something to look into. It’s possible that AI is suggesting contacts even if the senders don’t realize it.
In my experience, these mix-ups usually happen on the sender's side. They might have accidentally created a local contact that's incorrect or their company might have a faulty external contact saved with the wrong email address. Another possibility is that the exec was CCed on a previous email, so when they hit 'reply all,' it went to the exec instead of the shared mailbox. They might then just change the subject line and delete the original message content.
That makes sense, but these senders are all using private Gmail accounts and they don’t even know the exec, so it’s puzzling.

Exactly! I’ve been asking people to check their Google contacts to see if the email has been saved by mistake.