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Cortana fail: Microsoft's AI assistant embarrasses Satya Nadella during live keynote presentation

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Microsoft CEO Satya Nadella walks in front of the new Cortana logo as he delivers a keynote address during the 2014 Microsoft Build developer conference on April 2, 2014 in San Francisco, California. Satya Nadella delivered the opening keynote to kick off the 2014 Microsoft Build developer conference which runs through April 4.  (Photo by Justin Sullivan/Getty Images)

Microsoft CEO Satya Nadella walks in front of the new Cortana logo as he delivers a keynote address during the 2014 Microsoft Build developer conference on April 2, 2014 in San Francisco, California. Satya Nadella delivered the opening keynote to kick off the 2014 Microsoft Build developer conference which runs through April 4. (Photo by Justin Sullivan/Getty Images)

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Microsoft CEO Satya Nadella walks in front of the new Cortana logo as he delivers a keynote address during the 2014 Microsoft Build developer conference on April 2, 2014 in San Francisco, California. Satya Nadella delivered the opening keynote to kick off the 2014 Microsoft Build developer conference which runs through April 4. (Photo by Justin Sullivan/Getty Images)

Microsoft CEO Satya Nadella attempted to show off Cortana's capabilities during a keynote speech when it let him down in spectacular fashion.

We’ve all been there. We try to issue a voice command and our digital assistant gets it completely muddled. But Microsoft CEO Satya Nadella is the last person who wants to be let down, especially when he’s in the middle of demonstrating what Microsoft’s Cortana is capable of.

Nadella was delivering a keynote address at Salesforce's annual Dreamforce conference. He was demonstrating some productivity tools, and occasionally showed off what Windows 10 had to offer.

Then he called upon Cortana. “Show me my most at-risk opportunities,” he told the digital assistant.

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But she got it completely wrong and instead opened a Bing search results page for "Show me to buy milk at this opportunity."

He tried again and Cortana opened reminders. He gave Cortana one last chance at redemption before acknowledging that it wasn’t going to work. The snafu, which you can watch for yourself, starts at 10:30 in the video.

Cortana has been integrated into Windows 10. It is currently only available in certain regions.


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