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Gmail plugin Boomerang arrives on iOS with a voice assistant

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After four years of Android only

Credit: Boomerang

Gmail and Microsoft Outlook plugin Boomerang comes to iOS today, and it’s got a built-in AI voice assistant. The app syncs your email so that you essentially have two different apps to view your mail in, but it gives you tools Gmail and Outlook have yet to offer, like the ability to pause your email notifications for hours or weeks and send an email chain back to yourself as a reminder to follow up when needed. It’s taken Boomerang over four years to release its iOS app after launching on Android, and the latter isn’t getting the AI voice assistant for now.

Boomerang is also getting a few updates beyond its voice assistant. On the iOS app, you can swipe to the left on an email, and then move, mark, star, or delete the email with the flick of a finger. I tested out exactly how well Boomerang’s voice assistant works on iOS. The good news: the assistant can hear you over mild background noise, pause your emails on command, find what emails you need to respond to, and estimate the time it’ll take. It can even draft an email for meetings you need to reschedule. The bad news? Boomerang’s AI assistant is rudimentary, and it’s only trained for very specific commands; one or two wrong words, and you’ll get an “unknown command” error.

First, you have to toggle on the assistant in Settings. Then you can say “Hey Boomerang, brief me,” and in a very monotone voice, the AI assistant will show your next three meetings, and several numbers indicating how many minutes it will take to get through your emails. Boomerang’s founders, Alex Moore and Aye Moah, used an old product they had, called the Email Game, where they had people check and answer their emails on a timer, as their baseline to which they then applied machine learning. This feature was not so useful for me, as I skim PR emails based on keywords and delete if I see my name misspelled horrendously or another media’s name copy pasted instead of The Verge. An 800-word email written in graduate school-level English might take 10 minutes to go through based on Boomerang’s estimate, but if it’s spam, it only takes seconds to delete it right away without a response.

The rest of the commands don’t trigger a voice response, only a silent action, since the assumption is that you’ll be talking to Boomerang at work and maybe during a meeting. You can also say “Reschedule my meeting with so-and-so,” and the AI assistant will automatically create a draft email for you that begins, “I can no longer make it to the meeting at 2PM. Can we reschedule?” If you have multiple contacts of the same name, the assistant is smart enough to figure out the exact one you’re having the meeting with, so that you don’t send an email to the wrong John or Jack. It’s a convenient feature, but the draft email leaves out all the apologies and excuses I would normally include, so I’d have to rewrite most of it anyway. And since Boomerang is a plugin for Gmail and Outlook, it doesn’t sync with Apple’s calendar app.

Another command you can try is “Show me emails I need to respond to.” This one searches through all your emails, so it takes longer to load. It relies on machine learning to comb through sentences for phrases like “please let me know.” Does it work well? It could use improvement. It showed me a vacation notice from my editor as something that I needed to answer. Plus, it lacks the human ability to differentiate the spammers who would love you to answer from the legitimate pitches that deserve a response.

Command: “Show me emails I need to respond to.”

You can also command the Boomerang assistant to “Find me all emails with images from June,” which works, but seems to have some filtering issues, like including some pesky emails outside of June in the results. “Pause my email for such-and-such hours” is more reliable and stable to use. Boomerang’s email pausing function just hides all incoming mail for the time frame you set in a separate label until you’re ready to view it again. And commanding Boomerang to pause email makes the email paused on all platforms: mobile, web, and the Thunderbird desktop app.

The assistant is also not very hands-free. In order to activate the voice assistant, you need to first unlock your phone and then open Boomerang. Alternatively, in a chain reaction of assistants, you could ask Siri to open Boomerang and then talk to the Boomerang assistant from there. Moore and Moah say they’re speaking to Apple about fixing this in the future.

Boomerang’s voice assistant is a good first step, but it still has a lot of room to improve. The app itself is functional, but it turns off Spotify music whenever I open an email, and it loads slightly slower than Gmail. I’ll still be keeping the app on my iPhone solely for the ability to pause my email on the weekend through voice command. Hopefully, the minor issues that the assistant and iOS app have can be ironed out in future patches.