A method, computer system, and computer program product for contextually searching an electronic mail system is provided. The embodiment may include generating a contextual language set based on a language tag assigned to each electronic mail message within an electronic mailbox, whereby the generated contextual language set includes a first language and a second language. The embodiment may also include receiving a search term. The embodiment may further include identifying the received search term is drafted in the first language. The embodiment may also include generating a root character string of the identified search term. The embodiment may further include executing a search query of electronic mail messages within the electronic mailbox drafted in the first language using the generated root character string. The embodiment may also include executing a search query of electronic mail messages within the electronic mailbox drafted in the second language using the identified search term.