BENFEI DisplayPort to VGA Cable, 1.8M Display Port of Computer/Laptop to VGA of Monitor/Projector Gold-Plated Adapter (Not Bidirectional,Not Compatible with HDMI or USB)

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https://en.wikipedia.org/wiki/DisplayPort Opens a new window (Article indicates passive DP/HDMI adapters are possible, so I don 't know why a passive VGA>HDMI wouldn't be possible but I've never seen one) While you can go from a displayport to VGA monitor with a basic adapter(displayport provides power, where VGA doesn't) , I don't believe it's possible (and the your link mentions) that its not possible to go from VGA to DisplayPort, what's powering the conversion of the signal? Has the computer in question ever supproted HDMI and VGA output at the same time? Not all computers\video cards support output on every port at once. You should try using a Display port to USB and just drop the VGA all together.

VGA on the other hand is analog and requires extra equipment on the monitor side to convert analog to digital.If you are going from analog source (VGA) to a digital out like HDMI or DisplayPort, the adapter typically needs to be powered and usually has a little micro usb port on it for such purposes. It might be the other way around.. it's always hard to remember. Long story short, it's cheaper to go all digital from a manufacturing perspective, no more A to D conversion, and the picture looks better anyways. They probably just don't have the A to D hardware in the monitor and really didn't gear the thing for people putting the adapter on the other end.

If you are going from analog source (VGA) to a digital out like HDMI or DisplayPort, the adapter typically needs to be powered and usually has a little micro usb port on it for such purposes. so what I'm trying to find out is if there is another adapter i could use to get the second monitor to connect and work properly.

For analog VGA/YPbPr and dual-link DVI, a powered active adapter is required for compatibility and does not rely on dual mode. Active VGA adapters are powered by the DisplayPort connector directly, while active dual-link DVI adapters typically rely on an external power source such as USB I have a problem in getting one of my monitors to work through a VGA connection using a VGA to Display Port adaptor as the monitor only supports VGA input.