Abstract: Provided herein are systems, methods, and non-transient computer-readable storage media for providing contextualized responses using a virtual coworker within an email account. The disclosed techniques access an email thread, set a conversation context window to encompass the entire email thread, identify contextually relevant keywords within the subject line and email body, and search the email account for related email messages. A context library is created, comprising the email message and related email messages found in the email account. A response is generated based on user input derived from the context library, using a combination of prompts derived from natural language analysis and pre-programmed prompts. Additional features include analyzing the context library to define user input, engineering the initial prompt for the response, incorporating a knowledge base, reading attachments, and implementing digital security measures.