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For example the Alienware m17x offers 3 connections, HDMI, DisplayPort, and VGA. Is it possible to connect two independent external monitors, one through the DisplayPort and one through the HDMI port?

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That's actually an interesting question. Have you tried it already? For my Intel GMA it doesn't work. It is a dual head GPU because it can connect to two screens (to the laptop display and the VGA or DVI port). For anything different you would need a triple/quad head GPU, two GPUs or at least the possibility to switch from the Laptop screen to one of the external connectors. – Daff Aug 28 '09 at 21:22
    
My current laptop only supports hdmi/vga. I'm looking to replace it with one that will support two digital outputs, hdmi, dvi, displayport, etc. I just can't find any reliable information on how well they will work together... – Steph Aug 30 '09 at 14:34
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Simple answer is yes so long as your drivers support it. It would certainly be possible if you were using a usb displayport adapter I'm just not sure whatever chipset your running would support different output to 3 connections (assuming you want to extend your desktop not just have it cloned on multiple screens)

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