Cortana may not be the personal assistant she once was, but a new update as part of the Windows Insider Dev Channel means that her capabilities to find files have improved. The new "File Skill" in the Cortana app appears in the new Windows 10 Insider Preview Build 20270, part of the Dev Channel. In this experimental app, Cortana's skills have been honed to the point where she can find files in the cloud, with a better understanding of what you're looking for. If your PC is enrolled in the Windows 10 May 2020 Update or later, some of these capabilities will already be available. As long as you have speech recognition enabled on your PC, you can ask Cortana "find my recent files," and it should unearth the last two or three files you've used on your PC.

Lenovo recently released a new combination desktop program/Windows Store app that helps add even more power to Cortana on Windows 10 PCs. Lenovo's Reachit lets you take Cortana into places it's never been before by connecting the digital assistant to your files within the likes of Dropbox and Google Drive. Lenovo released Reachit in beta form in 2015, but now it's available for anyone to use. First, you install the Windows Store version of Reachit. Once you've done that, you'll be prompted to install a desktop program as well.