The contribution of context information to content management is of great importance. The increase of storage capacity in mobile devices gives users the possibility to maintain large amounts of content to their phones. As a result, this amount of content is increasing at a high rate. Users are able to store a huge variety of content such as contacts, text messages, ring tones, logos, calendar events, and textual notes. Furthermore, the development of novel applications has created new types of content, which include images, videos, MMS (multi-media messaging), e-mail, music, play lists, audio clips, bookmarks, news and weather, chat, niche information services, travel and entertainment information, driving instructions, banking, and shopping (Schilit & Theimer, 1994; Schilit, Adams, & Want, 1994; Brown, 1996; Brown, Bovey, & Chen, 1997). The fact that users should be able to store the content on their mobile phone and find the content they need without much effort results in the requirement of managing the content by organizing and annotating it. The purpose of information management is to aid users by offering a safe and easy way of retrieving the relevant content automatically, to minimize their effort and maximize their benefit (Sorvari et al., 2004). The increasing amount of stored content in mobile devices and the limitations of physical mobile phone user interfaces introduce a usability challenge in content management. The physical mobile phone user interface will not change considerably. The physical display sizes will not increase since in the mobile devices the display already covers a large part of the surface area. Text input speed will not change much, as keyboard-based text input methods have been the most efficient way to reduce slowness. While information is necessary for many applications, the human brain is limited in terms of how much information it can process at one time. The problem of information management is more complex in mobile environments (Campbell & Tarasewich, 2004). One way to reduce information overload and enhance content management is through the use of context metadata. Context metadata is information that describes the context in which a content item was created or received and can be used to aid users in searching, retrieving, and organizing the relevant content automatically. Context is any information that can be used to characterize the situation of an entity. An entity is a person, place, or object that is considered relevant to the interaction between a user and an application, including the user and the applications themselves (Dey, 2001). Some types of context are the physical context, such as time, location, and date; the social context, such as social group, friends, work, and home; and the mental context, which includes users’ activities and feelings (Ryan, Pascoe, & Morse, 1997; Dey, Abowd, & Wood, 1998; Lucas, 2001). By organizing and annotating the content, we develop a new way of managing it, while content management features are created to face efficiently the usability challenge. Context metadata helps the user find the content he needs by enabling single and multi-criteria searches (e.g., find photos taken in Paris last year), example-based searches (e.g., find all the video clips recorded in the same location as the selected video clip), and automatic content organization for efficient browsing (e.g., location-based content view, where the content is arranged hierarchically based on the content capture location and information about the hierarchical relationships of different locations).