To a lot of people watching the technology world and digital assistants, Microsoft's Cortana often ranks low on the list of options. A lot has happened since 2013, when Microsoft began putting Cortana into Windows Phones, including the death of that platform. But in 2019, the voice assistant is getting some significant revisions, including contextual-based conversational abilities as announced at the Build developer conference this week in Seattle. To get some answers about why contextually-aware artificial intelligence (AI) is a considerable breakthrough, and what's coming next for Cortana, we sat down with Andrew Shuman, Corporate Vice President of Cortana Engineering, and Daniel Klein, Technical Fellow at Microsoft Semantic Machines and a Professor at UC Berkeley, to find out. Best VPN providers 2020: Learn about ExpressVPN, NordVPN & more Years of redefining Cortana is not dead

While our 30-minute conversation ranged from skills to natural language processing and the problem with smart speakers, the big question we had was about the perception that Cortana is a dead platform. Shuman was emphatic. "Cortana is not dead," he said. "Fundamentally it is a foundational horizontal piece … like Microsoft Account, Microsoft Store, Microsoft Search." That may come as a surprise to many Cortana users. With the demise of mobile, Cortana has been undergoing an identify alteration during the last few years, including its development shifting to the Office team. One year ago, we wrote an article detailing Microsoft's plans for Cortana. At the time we said, "Microsoft's end goal is to integrate Cortana into Windows 10 seamlessly so that users don't even know they're using it." That point still holds. It was also in May 2018 when Microsoft acquired Semantic Machines, the Berkeley, Cali.-based AI company that powers the very conversational technology demonstrated this week at Build through Cortana. Microsoft is working on a Cortana experience that looks and feels like a normal text conversation. The chaos over Cortana, though, seems to be coming to an end. Recent significant revisions to the Cortana iOS and Android apps, and integrating it through more Microsoft endpoints (such as software and services) means that Cortana is on its way to being less app-centric and more people-centric, basing its knowledge graph on what we do, not just a single, siloed experience. Regarding the fragmented Cortana experience today in Windows 10 – something we criticized in our May 2019 Update review – Shuman said Cortana on Windows 10 will get a similar typing experience found now on iOS and Android, with a more refined and modern look. "That's just an interim step," Shuman said. This feature is a big deal because the Cortana experience on Windows 10 has slowly regressed during the last few Windows 10 feature updates. It started as a thriving virtual-assistant experience complete with day overviews, upcoming meetings, latest news, and weather forecasts, but is now an empty shell that does nothing but listen to you when you click it. The Cortana experience on Windows 10 today is something most people aren't going to want to use. It's not fun, nor informative, and it only works if you know what you're going to say. Many people don't feel comfortable talking to their PCs, so a redesigned Cortana experience that puts typing front and center is vital. This decision doesn't mean Microsoft is going to remove the ability to talk to Cortana on PC. It just means the user experience Microsoft is working on is going to better enable both use cases. Microsoft already does this with Cortana on Android and iOS; the user interface works equally well with voice or text, and the same can be expected for Cortana on Windows 10. If the experience looks and feels like a normal text conversation, like an SMS or iMessage conversation with a friend, people are much more likely to interact with Cortana. That's what Microsoft is hopefully working towards with the Cortana experience on Windows 10. Cortana is designed to help you stay productive, and typing is sometimes more natural than speaking. Talk like people Why contextual awareness matters