Microsoft’s Cortana is getting its biggest round of upgrades of the year with an integration into its Outlook email and Microsoft 365. Cortana can now read your emails to you, book and reschedule meetings, and provide personalized daily rundowns to help you prepare for meetings.

The work is a result of collaboration between Microsoft’s Cortana and Outlook teams and was leaked in a video a few days ago.

Cortana’s been able to find and write emails or surface reminders in your inbox for years, but Cortana in Outlook utilizes Microsoft’s key point extraction and summarization AI to deliver a synopsis of emails that lets people do quick triage — flagging and saving longer emails for later review or sending quick responses. “Play my email” also notes changes to your schedule that appear in email text and alerts you to any scheduling conflicts — like double-booked meetings.

Summaries can share context, like who else received the email and whether it was a follow-up or part of a thread, and when connected with Azure Active Directory, they can also factor company structure into the order of your email playlist, prioritizing emails from a manager, for instance.

The news is part of a larger effort to wed Cortana with Microsoft 365 products, Microsoft VP Andrew Shuman told VentureBeat in an interview at Microsoft offices in San Francisco.

Each email rundown begins by telling you how long it will take, and the feature is trained on your personal data and relationships.

Cortana’s meeting scheduler is enabled when Cortana is CCed in an email. Each person invited to a meeting will receive an email from Cortana allowing them to pick an agreeable time.

“This has been in various beta testings for I think over two years, maybe three years — with a lot of enterprise partners and customers — to try to really learn step by step how to make this great. And we’re excited to bring it out to production now,” Shuman said.

Cortana is also getting a masculine voice produced by a neural text-to-speech model. Major AI assistants like Cortana and Alexa were criticized in 2017 by people who believe it’s wrong for servile assistants to only speak with a female voice, Since then, Google and Apple have added male voice options.

“Certainly, we heard … a lot … that our users wanted this option, and that was the really big push to get it done. And you’re absolutely right, it’s been a story for a while,” Shuman said when asked why Microsoft chose to introduce a masculine voice now.

Finally, the daily briefing email comes with a quick look at your schedule, recommended documents to review ahead of a meeting and action items surfaced from conversational AI analysis of your emails. It also suggests scheduling focus time based on when a block of time becomes free in your schedule.

Cortana is also getting an upgrade to let users search and find information from the Microsoft 365 graph in Windows 10.

These upgrades were among a flood of announcements shared on the first day of Microsoft’s annual Ignite conference in Orlando, Florida.

Changes announced today are intended to enhance on-the-go mobile experiences for Microsoft Outlook’s 100 million monthly active users.

News today signals the continuance of Microsoft’s effort to focus Cortana on productivity and workplace applications.

“We are really focusing on this experience here, embedding across M365. That’s really the message,” Shuman said.