Techniques for expanding capabilities of a computing shell, which exposes services provided by an OS and which is separated from a kernel of the OS, by enabling a command line interface (CLI) of the shell to have context aware capabilities. An event in which a command is entered in the CLI is detected. The CLI displays a command decoration that is selectable and that, when selected, triggers display of a menu comprising a command suggestion. The command suggestion is generated based on a context associated with the command. In response to selection of the command decoration, the menu is displayed. This menu includes the command suggestion. In response to selection of the command suggestion, the computing shell automatically executes the command suggestion.