A woodchuck daemon, a network monitor and data transfer manager. The woodchuck daemon monitors the network and user-behavior to predict when to initiate transfer tasks. Applications that are woodchuck enabled register streams (e.g., RSS feeds, EMail mailboxes) with woodchuck as well as their constiuent objects (e.g., PodCasts, EMails). When Woodchuck detects good network conditions, e.g., the device is attached to power and there is free WiFi, it predicts what data (of the registered objects) the user will likely need in the near future based on historical user behavior and user and applications hints, and initiates their transfer.