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An Outlook add-in warns you when its AI thinks you’re about to email the wrong person or file.

Nearly every week, we’d hear at work about how somebody’s sent out some confidential email to the wrong company and how we’re now in jeopardy. They’d start typing in the name of the person they mean to send the sensitive information to and just click the first entry in the auto-complete list. The first thing proposed was to disable the Outlook auto-complete, as that was thought to be the culprit.

Needless to say, the users revolted. We’d just taken away a productivity tool and now they had to go find the email address of every single person they wanted to email. Since everyone had grown so reliant on the auto-complete, nobody had created contacts for any of these people and everyone was angry. They’d have to go into old emails, copy the email address of the people they wanted, and paste them into the email. They’d grab extra symbols around the email as they’d quickly try to do this. It was a nightmare. Within a week, we were told to re-enable the feature.

I had an idea: why couldn’t you use AI to tell if somebody was about to email the wrong person? Sure, it was easy to miss [email protected] wasn’t the same as [email protected] as a human, but a computer wouldn’t make that mistake nearly as easily. So I started working on my nights and weekends on a way to create a “spellcheck” for recipients. I made an Outlook extension that reads your email, gets to know your habits, and can tell if you’re about to email the wrong person. I started thinking that I could probably easily have it detect if you missed an attachment, so I added that feature as well. A lot of testing later and I had Jiminy.