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Whenever the user selects a new configuration which doesn't define a particular preprocessor macro, MonoDevelop will not reflect the change in the code highlighting. For instance
// Debug configuration defines the DEBUG symbol and it's the active configuration
string debugVar = null; // <- highlighted and colorized
// user switches configuration to Release which does not define DEBUG
string debugVar = null; // <- still highlighted and colorized
In order for the editor to refresh the display the user needs to start typing.