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Can I connect a Dell laptop (Latitude E7440) that uses an HDMI cable to a Dell monitor that uses a VGA cable?

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You will have better luck using the mini-DisplayPort port to adapt to VGA. The 7440 has mDP right next to HDMI on the back plane of the chassis:

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Googled 'Latitude E7440 vga' and the result was ' On the other hand, you’ll need to carry a VGA adapter to connect it to the old video projector in the boardroom.'

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