Disclosed are methods, systems, and machine readable mediums which provide for an automatic image scaling that may be utilized in a variety of contexts, including for scaling images inserted into documents. The image may be scaled based upon one or more scaling features that may be utilized alone or in combination. Scaling features may be described by scaling feature categories, although as will be appreciated, the scaling features may be placed in one or more categories. Example feature categories may include image characteristics; image content; content of the document and context of the image within the document; past user behavior and preferences; and the like.