Subtitles section Play video Print subtitles We will show you how to connect both a first-generation and second-generation Apple Pencil to the iPad. Unscrew the pencil cap and plug the Apple Pencil into the charging port of the iPad. Unlock your iPad and tap on "Pair." Launch the pencil onto the magnetic side of the iPad. A pop-up will appear asking if you want to pair it. Tap "Pair." Your pencil will be paired until you restart, turn on airplane mode, or connect it to another iPad.