Any.do is releasing a powerful new version of its popular to-do app. Available first on iOS and coming soon to Android, it brings the two features that CEO Omer Perchik says were most requested from its users: an integrated calendar and real-time sync. But Perchik is more eager to talk about the third feature, launching in a limited beta for a subset of users: a personal assistant.

When you enter a task into Any.do, the company’s servers will analyze it to see if it’s the sort of thing a chatbot or a human assistant could help you accomplish. If so, a button pops up to launch a chat with said bot or human, who then takes care of it for you.

This is the part where you, like pretty much everybody who has tried a virtual assistant or chatbot, will roll your eyes and assume it’s going to be a mess. Despite getting a whole lot of attention this year, chatbots haven’t replaced apps as the primary way in which we interact with our phones. And assistants from app makers have had an even harder time — they lack both the data and the deep integration into the OS that’s often necessary to make them useful.

But Any.do, Perchik says, has solutions to both of those problems. Users enter more than 1 million tasks a day into the app, and Any.do has been analyzing them anonymously for years. So the company comes to the bot game with a deep sense of its users’ top priorities, and where a bot or a human assistant could help. If your task is “Finish the TPS report,” the assistant won’t show up. If it’s “Make reservations for dinner” or “Buy flowers for mom” (the perennial chatbot classic), it’s more likely to appear.

As for integrating into the OS, Any.do is essentially sidestepping the whole problem. The assistant shows up only in the form of a little blue button next to your tasks — but only the tasks that Any.do knows for a fact that its services can achieve. And it doesn’t show up right away, either — the idea is that you dump all your tasks into your list when you think of them, and then later when it’s time to Start Doing Work, some of them will be solvable by a bot.

Most chatbots and assistants — from Siri to Allo to Facebook M — make you go to the bot, ask a question, and cross your fingers that it can figure it out. And when they inevitably can’t, you get annoyed. Any.do is taking the opposite approach: it only comes to you when it can help.

The assistant only appears when it will actually work

Perchik claims that up to a third of all tasks that get entered into Any.do could be accomplished with an assistant’s help. And when it comes to deciding whether to route the task to a chatbot or to a human, there’s yet another thing that this flipped-assistant model knows: whether it’s cost-effective. So if you type in “Buy a television,” Any.do might be more likely to assign a real human to finish that task out for you. The company says it charges a 5 to 15 percent service fee for completing tasks like these.

As a business plan, it makes more sense than most of the other assistant or chatbot schemes out there. Any.do knows what people are trying to accomplish, so it can create or commission bots that are able to do those things. But while it makes sense for Any.do as a company, we won’t know if it makes sense for users until we are able to try it. If those assistant dots don’t appear when you think they should or if the assistant itself can’t do what it promises, we’ll be looking at yet another failed chatbot promise.

But even if the new intelligent feature is a flop, the core to-do app itself still looks pretty solid — and perhaps worth the $45/year asking price (as of this writing, it’s discounted to $26.99). It’s as cleanly designed as ever, with the “Moment” feature that helps you organize your list every day. The real-time sync is table stakes, of course, but a necessary addition for people who have more than one device in their life (read: everybody).

The calendar also has a clever feature called “1x1.” When you want to make an appointment with somebody, you can select a bunch of optional times. Any.do then fires off an email with all of your options presented as buttons. When your contact taps one, that’s when it fires off a calendar invite that’s compatible with most online calendaring systems.

The new version of Any.do is rolling out today to iOS users — but the Any.do assistant will only be available in limited form to users in the US for awhile.