Can this device output signal when all three plugs are in use?

No. The DVI and HDMI will both output at same time. However if you plug in the VGA output you will lose both DVI and HDMI outputs

Questions & Answers: StarTech.com DP2VGDVHD Travel A/V adapter: 3-in-1 DisplayPort to VGA DVI or HDMI converter

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Item#: N82E16812400573
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StarTech.com DP2VGDVHD Travel A/V adapter: 3-in-1 DisplayPort to VGA DVI or HDMI converter

Connect a DisplayPort-equipped PC to an HDMI, VGA or DVI Display
Compatible with DisplayPort-equipped Desktop or Laptop computers such as Dell Optiplex or Ultrabook
DisplayPort to DVI / DisplayPort to VGA / DisplayPort to HDMI / DP to DVI / DP to VGA / DP to HDMI / DisplayPort 3-in-1 Converter / BYOD DP Converter
Carry with your laptop and connect to any HDMI, DVI or VGA display
Similar to MDP2VGDVHD

$50^.99 –