The present invention is directed to a secure messaging assistant that provides secure two-way communications between a user device and a server. The user can conduct a natural language conversation with the secure messaging assistant ask medical questions and enter symptoms that the user is experiencing. The secure messaging assistant uses natural language processing to return, in near real-time, medical conditions that are responsive to the user's input and which account for the user's own medical history (e.g., securely stored electronic medical history). The secure messaging assistant prevents the user from disclosing private or sensitive information to an internet based search engine, in the quest for medical advice.