When playing a video in Safari on your Mac, you can Control+click on it and select Enter Picture In Picture. But this doesn’t seem to work on YouTube videos. When you click on a YouTube video, you get a special context menu from YouTube instead of the default macOS one. The trick is to leave this context menu there without selecting anything, and then Control+click the video a second time to get the macOS context menu with the Enter Picture In Picture option.
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