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Basically, I'm wondering with the proper cables if can hook up an additional monitor to my late 2009 21.5" iMac. I know the 27" iMacs are able to be hooked up to external monitors, I'm just worried I won't be able to in the 21.5". Does anyone know if this will be possible?

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The support page shows that you can connect it to an external monitor.

Apple Mini DisplayPort video port

Using the Mini DisplayPort video output port, mirror video or extend the size of your Mac OS X desktop (extended desktop mode) with a compatible DVI (Digital Visual Interface) display or VGA (Video Graphics Display) or projector using the appropriate Mini DisplayPort adapter:

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Actually the next paragraph limits that to just 27's.:

Apple Mini DisplayPort video port

Using the Mini DisplayPort video output port, mirror video or extend the size of your Mac OS X desktop (extended desktop mode) with a compatible DVI (Digital Visual Interface) display or VGA (Video Graphics Display) or projector using the appropriate Mini DisplayPort adapter:

For Single Link DVI displays, use the Mini DisplayPort to DVI Adapter (MB570Z/A).
For Dual-Link DVI displays, use the Mini DisplayPort to Dual-Link DVI Adapter (MB571Z/A).
For VGA displays or projectors use the Mini DisplayPort to VGA Display Adapter (MB572Z/A).

Video mirroring

With video mirroring, you can see the image that is on the iMac flat-panel display on an external monitor, television, or projector.

Extended desktop mode

Connect an external display and use that area in addition to the built-in display for your desktop.

Audio output

The iMac (Mid 2010) supplies an audio signal from the Mini DisplayPort. For this feature, use Mini-DisplayPort to HDMI adapters that conform to the VESA v1.1a DisplayPort Interoperability Guidelines.

The Mini DisplayPort video port on the 27-inch iMac also supports video input from DisplayPort compliant sources.

Target Display Mode

Use the 27-inch iMac display as an external display for another computer, like a MacBook Pro. Return to the iMac screen by pressing Command + F2 on the keyboard. Note: Requires Mini DisplayPort to Mini DisplayPort cable or a converter that converts other electrical, video and audio protocols to DisplayPort compliant signals. Read more about using this feature in Using a 27-inch iMac as an external display.

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