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Context menu does not appear on second monitor. Dragging MonoDevelop to the primary monitor and then they do appear.
My configuration is an MBA running OS X 10.7.2 with the second monitor plugged in via the Display Port. I'm running MD 2.8.5.
What is your monitor layout?
I'm also going to need to know which context menus, because that may make a difference.
Is the MB Air monitor above? below? to the left? or to the right of the thunderbolt display?
The context menus for the solution (left pane).
My external monitor is above the MBA's monitor (from the mini DisplayPort, not Thunderbolt port).
I can't reproduce on MonoDevelop 126.96.36.199 (although I did just find/fix a multi-monitor issue for debugger tooltips when MD was on the primary screen in your setup that our CEO mentioned to me a minute ago).
I think this fix that made it into 2.8.6 may have fixed your particular issue:
Author: Jeffrey Stedfast <email@example.com>
Date: Fri Dec 16 18:46:57 2011 -0500
[TextEditor] Fixed context-menu placement for vertical multi-monitor setups
(the [TextEditor] bit is misleading, it actually fixes a GtkWorkarounds method to reposition context menus that is shared between the text editor and other areas of MD)
Marking as Fixed, but if you experience this with MonoDevelop 188.8.131.52, reopen and I'll dig into it again.