A system is disclosed for checking grammar and usage using a flexible portfolio of different mechanisms, and automatically providing a variety of different examples of standard usage, selected from analogous Web content. The system can be used for checking the grammar and usage in any application that involves natural language text, such as word processing, email, and presentation applications. The grammar and usage can be evaluated using several complementary evaluation modules, which may include one based on a trained classifier, one based on regular expressions, and one based on comparative searches of the Web or a local corpus. The evaluation modules can provide a set of suggested alternative segments with corrected grammar and usage. A followup, screened Web search based on the alternative segments, in context, may provide several different in-context examples of proper grammar and usage that the user can consider and select from.