Prioritizing thumbnail previews based on message content

Systems for prioritizing thumbnail previews within a message are described. A thumbnail prioritization application may automatically identify files that are most applicable and/or relevant to a message. When more than one file is applicable to a message, each file may be ranked based on its predicted relevance to the message. In this way, a subset of relevant files is identified, as well as identifying the most relevant files within the subset. Thumbnail previews may further link directly to a corresponding file within storage, enabling recipients of a message to easily and efficiently identify and directly access files that are most applicable to the message. Because relevant files are automatically identified, neither the sender nor the recipient(s) are required to search through multiple files to locate applicable files. Accordingly, user burden is reduced and user efficiency is increased, leading to a better overall user experience.