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I am a developer and I have a two monitor setup.

Many times I want to keep a debug console window on top of all windows without blocking my source code viewer (monitor 1) and emulator program (monitor 2). I usually drag the console at to the common edge of both monitors, so I can view the console with minor obstruction to the source code viewer and emulator program.

Did anyone came across any windows application which will automatic make a window always on top when being positioned to span across two monitors?

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I don't know of anything that will automatically do it. But use a freeware program called Desk Pins to set any windows I want to stay on top.

To make any window stay on top, you click the Desk Pins icon in the system tray and then you click the window you want to stay on top, it then puts a small little thumbtack icon next to the minimize button showing that it is being held on top.

If you want to make a window not stay on top, you click the pin next to the minimize button and removes the pin and makes the window normal again.

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You can try the free Eusing Auto Window Manager, although its description doesn't mention multi-monitor.

A commercial option may be ZMover (trialware).

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