First came Slack, then came Skype — at least to the messaging app bot game.

Microsoft, which owns Skype, demoed how an updated Cortana would integrate travel expense reporting and hotel booking at its Build conference in San Francisco this week. Cortana now works in the background of the Skype app, understanding both video and SMS conversations within the app, to proactively make suggestions and perform tasks relevant to the conversation and upcoming events a traveler refers to. Cortana is exclusively for Android smartphones and Microsoft’s Windows operating system but Skype isn’t its only domain. As Microsoft explained, Cortana also integrates with a variety of Windows products including Outlook.

Microsoft’s been discreet about how it views itself in the travel ecosystem and no travel brands have launched a Skype bot. It did, however, announce that Cortana can automate expense reporting through Outlook based on incoming emails, though that’s separate from Skype’s bots.

Skype is also more consumer-focused than Slack, which built its business as a messaging platform for companies. Adding bots to Skype’s video messaging creates a new learning curve beside SMS messaging that travel brands haven’t yet grasped.

“This is part of the proactive action capabilities we announced at [Microsoft’s Build conference],” Microsoft told Skift. “Developers can now leverage Cortana’s holistic understanding of the user and their context to proactively surface their app, websites and in the future, bots, to users in just the right the context to drive greater engagement.”

“For consumers, this means that Cortana is now evolving to do things for you when she anticipates that you need help by proactively prompting you with timely suggestions about things, such as expense reports, that she can help with and even connect you with an expert to get it done on your behalf. [Through Microsoft’s Windows Ink] you can even turn your Sticky Note into a reminder, for example. When you type in a flight number, Cortana will recognize it and allow you to track that information [using Cortana] across your devices.”

A Westin Hotels & Resorts Skype bot was mentioned during the demo (see video below), but Westin told Skift that Microsoft used the brand as a hypothetical example to demonstrate the bots and that no Westin bot has been implemented and the hotel hasn’t had further discussions with Microsoft about an integration.

With the Westin example, Cortana introduced the Westin bot into a conversation between a traveler and a friend she’s planning to visit in Dublin. Cortana pre-populated the Westin bot with trip dates and destination. After booking a room at The Westin Dublin, the Westin bot left the conversation for chatting to continue between both friends.

The remaining mystery: Microsoft wouldn’t say why it believes travelers want to book travel in this context or offer color about the merging of messaging and travel. Kayak’s Slack bot integration shows that early travel brand adopters brew a lot of uncertainty for travelers. But once kinks get worked out, imagine the convenience of having your favorite hotel or airline integrated into a messaging conversation when chatting with friends and family about upcoming plans to visit them.

Photo Credit: A demo of a hypothetical Westin bot within Microsoft's Skype app at Microsoft's Build conference in San Francisco this week. CNET