A system for automatically providing different levels of formality controls in a communication is disclosed, in which a formality level is determined based on a current communication context. The formality level is used to enable an appropriate level of automatic checking of the communication contents. The determination of a formality level for a communication may be based on any specific context information regarding the participants and/or contents of a communication. including but not limited to the relative positions of participants within an organizational hierarchy (“organizational distance”), the professional relationships of the participants (e.g. service provider to client/customer), the frequency of communications between participants, the geographic locations of participants, the number of previous errors in the communication contents, configurable participant preferences, express communication settings by participants, etc. The determined formality level may be used to enable any specific type or level of automatic message contents checking, including but not limited to various types and levels of spell checking (e.g. location specific spell checking), grammar checking, acronym substitution, cultural filtering, etc. The disclosed system may determine organisational distances based on the contents of user directories, such as lightweight directory access protocol (LDAP) directories.